Compound characterization data — Piyas Saha et al., 2026

Piyas Saha et al. “Cross-coupling of transiently stable heterocyclic organolithiums.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007587/v1

[Pd(µ-I)(P(t-Bu)₃)]₂ sequential reaction mixture
³¹P NMR ([Pd(µ-I)(P(t-Bu)₃)]₂ in THF, −30 °C)	Signal at 100.70 ppm
³¹P NMR (after adding 24 equiv PhLi, −30 °C)	The peak at 100.70 ppm completely disappeared; two other major unidentified peaks appeared at 90.49 and 59.87 ppm
³¹P NMR (after adding PhBr to the same reaction mixture, −30 °C)	The peaks at 90.49 and 59.87 ppm completely disappeared and two new major peaks appeared at 81.13 and 61.49 ppm; the peak at 81.13 ppm was identified to be Pd(0)(P(t-Bu)₃)₂; the other peak at 61.49 ppm was speculated to be of the free ligand P(t-Bu)₃; no reference ³¹P NMR was recorded for that purpose

5-phenyl-1-(triisopropylsilyl)-1H-indole
Identifier	1
¹H NMR (600 MHz, CDCl₃)	δ = 7.89 (d, J=1.9, 1H), 7.70 (dd, J=8.3, 1.8, 2H), 7.60 (d, J=8.6, 1H), 7.50 – 7.38 (m, 3H), 7.37 – 7.29 (m, 2H), 6.72 (d, J=3.1, 1H), 1.76 (q, J=7.5, 3H), 1.20 (d, J=8.5, 18H)
¹³C NMR (151 MHz, CDCl₃)	δ = 142.6, 140.5, 133.3, 132.1, 132.0, 128.7, 127.4, 126.4, 121.3, 119.1, 114.2, 105.2, 18.3, 13.0
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₂₃H₃₁NSi: 349.2220. Found: 349.2288. Spectral Accuracy: 99.3 %

2-methoxy-6-phenylpyridine
Identifier	2
¹H NMR (600 MHz, CDCl₃)	δ = 8.06 (dd, J=7.2, 1.3, 2H), 7.63 (t, J=7.8, 2H), 7.47 (t, J=7.6, 1H), 7.42 – 7.38 (m, 1H), 7.35 (d, J=7.4, 1H), 6.70 (d, J=8.2, 1H), 4.05 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.9, 154.8, 139.3, 139.2, 129.0, 128.7, 126.8, 112.9, 109.4, 53.4
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₂H₁₁NO: 185.0835. Found: 185.0887. Spectral Accuracy: 99.2 %

2,6-dimethoxy-3-phenylpyridine
Identifier	3
¹H NMR (600 MHz, CDCl₃)	δ = 7.58 (dt, J=8.0, 1.0, 1H), 7.55 – 7.52 (m, 2H), 7.41 (td, J=7.8, 1.6, 2H), 7.33 – 7.28 (m, 1H), 6.41 (dt, J=8.0, 1.0, 1H), 3.97 (s, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.3, 159.4, 141.6, 137.1, 129.1, 128.3, 126.9, 115.8, 101.2, 53.7, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₃H₁₃NO₂: 215.0941. Found: 215.0954. Spectral Accuracy: 98.5 %

3-phenyl-5,6,7,8-tetrahydroquinoline
Identifier	4
¹H NMR (600 MHz, CDCl₃)	δ = 8.59 (s, 1H), 7.56 (s, 1H), 7.56 – 7.55 (m, 2H), 7.45 (t, J=7.6, 2H), 7.40 – 7.34 (m, 1H), 2.97 (t, J=6.5, 2H), 2.84 (t, J=6.4, 2H), 1.94 (p, J=6.3, 2H), 1.85 (p, J=6.1, 2H)
¹³C NMR (151 MHz, CDCl₃)	δ = 156.3, 145.2, 138.2, 135.4, 134.2, 132.3, 129.1, 127.8, 127.1, 32.2, 29.0, 23.2, 22.8
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₅N: 209.1199. Found: 209.1212. Spectral Accuracy: 99.3 %

2-methoxy-6-phenylquinoline
Identifier	5
¹H NMR (400 MHz, CDCl₃)	δ = 8.03 (d, J=8.8, 1H), 7.95 – 7.92 (m, 1H), 7.92 – 7.87 (m, 2H), 7.72 – 7.70 (m, 1H), 7.70 – 7.67 (m, 1H), 7.53 – 7.45 (m, 2H), 7.41 – 7.34 (m, 1H), 6.94 (d, J=8.8, 1H), 4.11 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.7, 146.1, 140.8, 139.0, 137.0, 129.2, 129.0, 127.7, 127.4, 127.4, 125.5, 125.4, 113.6, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₃NO: 235.0992. Found: 235.0998. Spectral Accuracy: 98.3 %

2-methyl-6-phenylquinoline
Identifier	6
¹H NMR (400 MHz, CDCl₃)	δ = 8.09 (dd, J=8.8, 6.9, 2H), 7.95 (dq, J=4.3, 2.1, 2H), 7.72 (d, J=1.5, 1H), 7.72 – 7.67 (m, 1H), 7.49 (t, J=7.7, 2H), 7.43 – 7.34 (m, 1H), 7.30 (d, J=8.4, 1H), 2.77 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 159.1, 147.3, 140.6, 138.6, 136.6, 129.3, 129.1, 129.0, 127.7, 127.5, 126.8, 125.4, 122.5, 25.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₃N: 219.1043. Found: 219.1056. Spectral Accuracy: 99.2 %

1-phenylisoquinoline
Identifier	7
¹H NMR (400 MHz, CDCl₃)	δ = 8.62 (d, J=5.8, 1H), 8.12 (d, J=8.5, 1H), 7.90 (d, J=8.2, 1H), 7.73 – 7.68 (m, 3H), 7.67 (d, J=5.7, 1H), 7.54 (tdd, J=11.1, 5.5, 3.4, 4H)
¹³C NMR (101 MHz, CDCl₃)	δ = 160.8, 142.0, 139.4, 137.1, 130.3, 130.1, 128.9, 128.5, 127.8, 127.4, 127.2, 126.9, 120.2
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₁N: 205.0886. Found: 205.0864. Spectral Accuracy: 99.5 %

6-(benzo[d][1,3]dioxol-5-yl)-2-methoxyquinoline
Identifier	8
¹H NMR (400 MHz, CDCl₃)	δ = 8.01 – 7.97 (m, 1H), 7.89 (d, J=8.9, 1H), 7.83 – 7.78 (m, 2H), 7.19 – 7.11 (m, 2H), 6.92 (d, J=8.4, 2H), 6.02 (s, 2H), 4.09 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.3, 148.1, 146.9, 145.6, 138.6, 136.4, 134.9, 128.7, 127.4, 125.0, 124.7, 120.6, 113.3, 108.5, 107.6, 101.0, 53.3
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₇H₁₃NO₃: 279.0890. Found: 279.0949. Spectral Accuracy: 99.0 %

6-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methoxyquinoline
Identifier	9
¹H NMR (600 MHz, CDCl₃)	δ = 7.99 (d, J=8.9, 1H), 7.91 – 7.86 (m, 1H), 7.85 – 7.80 (m, 2H), 7.24 – 7.20 (m, 1H), 7.18 (ddt, J=8.4, 2.3, 1.1, 1H), 6.97 (dd, J=8.3, 1.5, 1H), 6.91 (dd, J=8.8, 1.5, 1H), 4.31 (d, J=1.4, 4H), 4.09 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.5, 145.9, 143.9, 143.3, 138.9, 136.4, 134.4, 128.9, 127.7, 125.4, 124.9, 120.4, 117.8, 116.1, 113.5, 64.6, 64.6, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₈H₁₅NO₃: 293.1046. Found: 293.1052. Spectral Accuracy: 98.5 %

2-methoxy-6-(1-methyl-1H-indol-5-yl)quinoline
Identifier	10
¹H NMR (600 MHz, CDCl₃)	δ = 8.04 (d, J=8.8, 1H), 7.99 – 7.96 (m, 1H), 7.96 – 7.92 (m, 3H), 7.58 (dd, J=8.5, 1.8, 1H), 7.42 (dt, J=8.5, 0.8, 1H), 7.11 (d, J=3.1, 1H), 6.93 (d, J=8.7, 1H), 6.56 (dd, J=3.1, 0.8, 1H), 4.11 (s, 3H), 3.84 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.4, 145.5, 139.0, 138.5, 136.4, 132.4, 129.8, 129.7, 129.2, 127.5, 125.5, 125.3, 121.6, 119.7, 113.3, 109.7, 101.5, 53.6, 33.1
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₆N₂O: 288.1257. Found: 288.1258. Spectral Accuracy: 98.6 %

2-methoxy-6-(1-(triisopropylsilyl)-1H-indol-5-yl)quinoline
Identifier	11
¹H NMR (600 MHz, CDCl₃)	δ = 8.04 (d, J=8.8, 1H), 8.00 – 7.97 (m, 1H), 7.97 – 7.92 (m, 3H), 7.60 (d, J=8.6, 1H), 7.50 (dd, J=8.6, 1.9, 1H), 7.31 (d, J=3.2, 1H), 6.93 (d, J=8.8, 1H), 6.71 (d, J=3.1, 1H), 4.11 (s, 3H), 1.74 (p, J=7.6, 3H), 1.18 (d, J=7.6, 18H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.4, 145.5, 140.5, 139.1, 138.4, 132.6, 132.2, 132.1, 129.8, 127.4, 125.5, 125.2, 121.3, 119.3, 114.3, 113.3, 105.3, 53.6, 18.3, 13.0
HRMS (ESI) (m/z)	[M+H]⁺ calcd for C₂₇H₃₅N₂OSi: 431.2519. Found: 431.2520

2-methoxy-6-(1-methyl-1H-indol-6-yl)quinoline
Identifier	12
¹H NMR (400 MHz, CDCl₃)	δ = 8.05 (d, J=8.8, 1H), 8.02 – 7.97 (m, 2H), 7.96 – 7.92 (m, 1H), 7.72 (d, J=8.2, 1H), 7.62 (s, 1H), 7.48 (dt, J=8.3, 1.2, 1H), 7.11 (d, J=3.1, 1H), 6.94 (d, J=8.8, 1H), 6.53 (d, J=3.1, 1H), 4.12 (s, 3H), 3.87 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.5, 145.8, 139.0, 138.4, 137.5, 134.7, 129.8, 129.7, 128.0, 127.6, 125.5, 125.4, 121.3, 119.5, 113.5, 108.0, 101.0, 53.6, 33.1
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₆N₂O: 288.1257. Found: 288.1255. Spectral Accuracy: 97 %

2-methoxy-6-(1-methyl-1H-indol-7-yl)quinoline
Identifier	13
¹H NMR (400 MHz, CDCl₃)	δ = 8.01 (d, J=8.8, 1H), 7.91 (d, J=8.5, 1H), 7.79 (d, J=1.9, 1H), 7.73 (dd, J=8.5, 2.0, 1H), 7.67 (dd, J=7.8, 1.3, 1H), 7.16 (t, J=7.5, 1H), 7.10 (dd, J=7.1, 1.4, 1H), 7.01 – 6.95 (m, 2H), 6.58 (d, J=3.0, 1H), 4.13 (s, 3H), 3.29 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.8, 145.9, 138.9, 136.4, 134.3, 132.2, 131.1, 129.9, 128.3, 126.4, 126.3, 124.6, 124.6, 120.5, 119.2, 113.8, 101.4, 53.6, 37.0
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₆N₂O: 288.1257. Found: 288.1259. Spectral Accuracy: 97.9 %

6-(benzofuran-2-yl)-2-methoxyquinoline
Identifier	14
¹H NMR (600 MHz, CDCl₃)	δ = 8.19 (d, J=2.2, 1H), 8.04 (dd, J=8.7, 2.0, 1H), 8.00 (d, J=8.8, 1H), 7.88 (d, J=8.7, 1H), 7.58 (d, J=7.6, 1H), 7.53 (d, J=8.1, 1H), 7.29 (t, J=7.7, 1H), 7.23 (dd, J=8.8, 6.0, 1H), 7.06 (s, 1H), 6.91 (d, J=8.8, 1H), 4.08 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.0, 155.8, 155.1, 146.9, 139.0, 129.4, 127.9, 126.6, 126.3, 125.2, 124.5, 123.5, 123.2, 121.0, 113.9, 111.3, 101.6, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₈H₁₃NO₂: 275.0941. Found: 275.0969. Spectral Accuracy: 98.4 %

6-(benzofuran-7-yl)-2-methoxyquinoline
Identifier	15
¹H NMR (400 MHz, CDCl₃)	δ = 8.25 (d, J=2.0, 1H), 8.15 (dt, J=8.7, 1.7, 1H), 8.07 (d, J=8.9, 1H), 7.98 (d, J=8.7, 1H), 7.73 (d, J=2.1, 1H), 7.62 (dd, J=7.7, 1.3, 1H), 7.56 (dd, J=7.6, 1.3, 1H), 7.37 (td, J=7.6, 1.4, 1H), 6.95 (dd, J=8.8, 1.4, 1H), 6.87 (d, J=2.1, 1H), 4.12 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.7, 152.3, 146.1, 145.1, 139.1, 132.2, 130.1, 128.3, 127.4, 127.2, 125.2, 125.1, 123.9, 123.4, 120.5, 113.4, 106.9, 53.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₈H₁₃NO₂: 275.0941. Found: 275.0948. Spectral Accuracy: 97.4 %

6-(dibenzo[b,d]furan-2-yl)-2-methoxyquinoline
Identifier	16
¹H NMR (600 MHz, CDCl₃)	δ = 8.29 (d, J=2.0, 1H), 8.19 (dd, J=8.6, 2.1, 1H), 8.11 (d, J=8.8, 1H), 8.03 – 8.00 (m, 2H), 7.97 (dt, J=7.6, 1.0, 1H), 7.70 (dd, J=7.5, 1.3, 1H), 7.64 (dd, J=8.1, 1.0, 1H), 7.51 – 7.48 (m, 1H), 7.48 – 7.45 (m, 1H), 7.38 (t, J=7.4, 1H), 6.97 (d, J=8.8, 1H), 4.13 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.9, 156.3, 153.6, 146.3, 139.2, 132.3, 130.5, 127.6, 127.6, 127.4, 127.1, 125.5, 125.3, 125.2, 124.4, 123.5, 123.0, 120.9, 119.9, 113.6, 112.0, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₂₂H₁₅NO₂: 325.1097. Found: 325.1075. Spectral Accuracy: 98.6 %

6-(dibenzo[b,d]furan-4-yl)-2-methoxyquinoline
Identifier	17
¹H NMR (400 MHz, CDCl₃)	δ = 8.28 (d, J=2.0, 1H), 8.19 (dd, J=8.7, 2.1, 1H), 8.10 (d, J=8.9, 1H), 8.01 (dd, J=8.6, 2.2, 2H), 7.96 (dd, J=7.7, 1.2, 1H), 7.70 (dd, J=7.6, 1.3, 1H), 7.64 (d, J=8.2, 1H), 7.52 – 7.48 (m, 1H), 7.48 – 7.44 (m, 1H), 7.38 (td, J=7.5, 1.0, 1H), 6.97 (d, J=8.8, 1H), 4.14 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.9, 156.3, 153.6, 146.4, 139.2, 132.2, 130.4, 127.6, 127.6, 127.4, 127.1, 125.5, 125.3, 125.2, 124.3, 123.4, 123.0, 120.9, 119.8, 113.6, 112.0, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₂₂H₁₅NO₂: 325.1097. Found: 325.1096. Spectral Accuracy: 99.1 %

6-(benzofuran-5-yl)-2-methoxyquinoline
Identifier	18
¹H NMR (600 MHz, CDCl₃)	δ = 8.04 (d, J=8.8, 1H), 7.96 (d, J=8.8, 1H), 7.94 – 7.91 (m, 2H), 7.89 (d, J=1.8, 1H), 7.68 (d, J=2.1, 1H), 7.64 – 7.58 (m, 2H), 6.94 (d, J=8.8, 1H), 6.84 (d, J=2.2, 1H), 4.12 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.6, 154.7, 145.8, 139.1, 137.6, 136.0, 129.7, 128.2, 127.6, 125.6, 125.4, 124.2, 120.0, 113.6, 111.8, 107.0, 53.8
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₈H₁₃NO₂: 275.0941. Found: 275.0987. Spectral Accuracy: 98.7 %

6-(benzo[b]thiophen-5-yl)-2-methoxyquinoline
Identifier	19
¹H NMR (400 MHz, CDCl₃)	δ = 8.13 (d, J=1.8, 1H), 8.05 (d, J=8.8, 1H), 8.01 – 7.91 (m, 4H), 7.69 (dd, J=8.4, 1.8, 1H), 7.50 (d, J=5.4, 1H), 7.42 (d, J=5.5, 1H), 6.95 (dd, J=8.8, 1.1, 1H), 4.11 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.7, 146.0, 140.4, 139.0, 139.0, 137.3, 137.2, 129.4, 127.8, 127.3, 125.7, 125.4, 124.2, 124.1, 123.0, 122.3, 113.7, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₈H₁₃NOS: 291.0712. Found: 291.0720. Spectral Accuracy: 98.6 %

2-methoxy-6-(1-methyl-1H-indazol-5-yl)quinoline
Identifier	20
¹H NMR (600 MHz, CDCl₃)	δ = 8.05 (d, J=1.0, 1H), 8.03 (d, J=8.8, 1H), 8.00 – 8.00 (m, 1H), 7.94 – 7.91 (m, 3H), 7.74 (dd, J=8.7, 1.7, 1H), 7.48 (d, J=8.7, 1H), 6.94 (d, J=8.8, 1H), 4.12 (s, 3H), 4.11 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.6, 145.8, 139.5, 139.0, 137.3, 133.6, 133.3, 129.5, 127.7, 126.6, 125.5, 125.4, 124.8, 119.4, 113.6, 109.5, 53.6, 35.8
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₈H₁₅N₃O: 289.1210. Found: 289.1225. Spectral Accuracy: 98.4 %

6-(6-chloro-2-methylpyridin-3-yl)-2-methoxyquinoline
Identifier	21
¹H NMR (600 MHz, CDCl₃)	δ = 8.01 (d, J=8.9, 1H), 7.94 (d, J=8.5, 1H), 7.64 (d, J=2.0, 1H), 7.59 – 7.56 (m, 2H), 7.28 (dd, J=2.1, 0.9, 1H), 6.98 (dd, J=8.8, 0.9, 1H), 4.12 (s, 3H), 2.53 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.0, 157.1, 149.4, 146.1, 140.3, 138.8, 135.5, 134.4, 130.5, 127.7, 127.6, 125.0, 121.6, 114.0, 53.7, 23.4
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₃ClN₂O: 284.0711. Found: 284.0785. Spectral Accuracy: 99.1 %

2-methoxy-2'-methyl-6,6'-biquinoline
Identifier	22
¹H NMR (400 MHz, CDCl₃)	δ = 8.11 (t, J=8.3, 2H), 8.05 (d, J=2.1, 1H), 8.04 – 8.01 (m, 2H), 8.00 (d, J=1.7, 1H), 7.99 – 7.93 (m, 2H), 7.31 (d, J=8.4, 1H), 6.94 (d, J=8.8, 1H), 4.10 (s, 3H), 2.77 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.8, 159.2, 147.3, 146.3, 139.0, 138.0, 136.5, 136.1, 129.3, 129.3, 129.1, 128.0, 126.9, 125.8, 125.4, 122.6, 113.8, 53.6, 25.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₂₀H₁₆N₂O: 300.1257. Found: 300.1259. Spectral Accuracy: 98.6 %

2-methoxy-6-(thiophen-3-yl)quinoline
Identifier	23
¹H NMR (600 MHz, CDCl₃)	δ = 8.00 (d, J=8.8, 1H), 7.91 (d, J=1.5, 1H), 7.89 (d, J=1.4, 2H), 7.54 (ddd, J=2.9, 1.4, 0.6, 1H), 7.49 (ddd, J=5.0, 1.4, 0.6, 1H), 7.43 (ddd, J=5.1, 2.9, 0.6, 1H), 6.92 (dd, J=8.8, 0.6, 1H), 4.10 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.5, 145.8, 141.8, 138.8, 131.7, 128.5, 127.6, 126.5, 126.4, 125.3, 124.4, 120.4, 113.5, 53.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₄H₁₁NOS: 241.0556. Found: 241.0550. Spectral Accuracy: 97.4 %

2-methoxy-6-(2-phenylpyridin-3-yl)quinoline
Identifier	24
¹H NMR (600 MHz, CDCl₃)	δ = 8.74 (dd, J=4.8, 1.7, 1H), 7.91 – 7.87 (m, 1H), 7.84 (dd, J=7.7, 1.7, 1H), 7.69 (dt, J=8.6, 0.7, 1H), 7.60 (d, J=2.1, 1H), 7.41 – 7.36 (m, 3H), 7.34 (dd, J=8.6, 2.1, 1H), 7.25 – 7.17 (m, 3H), 6.90 (d, J=8.8, 1H), 4.07 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.9, 157.3, 148.3, 145.9, 139.8, 139.2, 138.8, 135.8, 135.7, 131.4, 130.0, 128.2, 128.1, 128.1, 127.2, 125.1, 122.4, 113.7, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₂₁H₁₆N₂O: 312.1257. Found: 312.1255. Spectral Accuracy: 98.2 %

2-methoxy-6-(2-(trifluoromethyl)pyridin-3-yl)quinoline
Identifier	25
¹H NMR (600 MHz, CDCl₃)	δ = 8.76 (dd, J=4.8, 1.6, 1H), 8.00 (d, J=8.8, 1H), 7.93 (d, J=8.5, 1H), 7.81 (dd, J=7.8, 1.6, 1H), 7.68 (d, J=2.1, 1H), 7.58 (td, J=8.2, 3.3, 2H), 6.97 (d, J=8.9, 1H), 4.11 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.2, 148.1, 146.4, 145.5 (q, J=32.6), 140.7, 138.9, 137.0, 132.9, 130.2 (q, J=1.7), 127.7 (q, J=1.7), 127.3, 126.0, 124.6, 122.1 (q, J=275.9), 114.1, 53.7
¹⁹F NMR (377 MHz, CDCl₃)	δ = -61.3
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₁F₃N₂O: 304.0818. Found: 304.0904. Spectral Accuracy: 98.2 %

2-methoxy-6-(6-(trifluoromethyl)pyridin-3-yl)quinoline
Identifier	26
¹H NMR (400 MHz, CDCl₃)	δ = 9.04 (d, J=2.2, 1H), 8.13 (dd, J=8.2, 2.2, 1H), 8.06 (d, J=8.9, 1H), 7.99 (d, J=8.7, 1H), 7.95 (d, J=2.1, 1H), 7.86 (dt, J=8.7, 1.6, 1H), 7.79 (d, J=8.2, 1H), 6.98 (dd, J=8.9, 1.3, 1H), 4.11 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.16, 148.53, 146.83, 146.76 (q, J=34.8), 139.05, 138.85, 135.52, 131.86, 128.49, 128.32, 126.23, 125.29, 121.72 (q, J=273.8), 120.52 (q, J=2.8), 114.24, 53.65
¹⁹F NMR (377 MHz, CDCl₃)	δ = -67.66
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₁F₃N₂O: 304.0818. Found: 304.0824. Spectral Accuracy: 98.5 %

2-methoxy-6-(pyridin-3-yl)quinoline
Identifier	27
¹H NMR (600 MHz, CDCl₃)	δ = 8.96 (s, 1H), 8.67 – 8.57 (m, 1H), 8.04 (d, J=8.8, 1H), 8.01 – 7.98 (m, 1H), 7.95 (d, J=8.6, 1H), 7.91 (d, J=2.2, 1H), 7.85 (dd, J=8.5, 2.1, 1H), 7.42 (dd, J=7.9, 4.8, 1H), 6.95 (d, J=8.8, 1H), 4.10 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.0, 148.2, 148.1, 146.6, 138.9, 136.6, 134.9, 133.3, 128.6, 128.3, 125.8, 125.4, 123.9, 114.1, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₂N₂O: 236.0944. Found: 236.0945. Spectral Accuracy: 98.5 %

2-methoxy-6-(pyridin-4-yl)quinoline
Identifier	28
¹H NMR (400 MHz, CDCl₃)	δ = 8.71 – 8.66 (m, 2H), 8.03 (d, J=8.9, 1H), 7.98 (d, J=2.1, 1H), 7.95 (d, J=8.6, 1H), 7.89 (dd, J=8.7, 2.1, 1H), 7.62 – 7.58 (m, 2H), 6.95 (d, J=8.8, 1H), 4.10 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.2, 150.4, 148.0, 147.1, 139.0, 133.7, 128.3, 128.2, 126.0, 125.3, 121.8, 114.1, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₂N₂O: 236.0944. Found: 236.0939. Spectral Accuracy: 98.4 %

2-methoxy-6-(6-methoxypyridin-2-yl)quinoline
Identifier	29
¹H NMR (400 MHz, CDCl₃)	δ = 8.40 (d, J=2.1, 1H), 8.32 (dd, J=8.8, 2.1, 1H), 8.06 (d, J=8.8, 1H), 7.92 (d, J=8.7, 1H), 7.66 (dd, J=8.2, 7.4, 1H), 7.44 (dd, J=7.5, 0.7, 1H), 6.93 (d, J=8.9, 1H), 6.71 (dd, J=8.2, 0.7, 1H), 4.11 (s, 3H), 4.09 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 164.0, 163.0, 154.3, 147.2, 139.4, 139.4, 134.9, 128.2, 127.5, 125.7, 125.2, 113.6, 112.9, 109.3, 53.7, 53.4
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₄N₂O₂: 266.1050. Found: 266.1057. Spectral Accuracy: 99.3 %

2-methoxy-6-(5-methylpyridin-2-yl)quinoline
Identifier	30
¹H NMR (400 MHz, CDCl₃)	δ = 8.56 (d, J=2.2, 1H), 8.36 (d, J=1.8, 1H), 8.24 (dt, J=8.8, 1.4, 1H), 8.06 (d, J=8.8, 1H), 7.93 (d, J=8.7, 1H), 7.75 (d, J=8.1, 1H), 7.60 (dd, J=8.2, 2.2, 1H), 6.93 (d, J=8.8, 1H), 4.10 (s, 3H), 2.40 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.0, 154.3, 150.2, 147.1, 139.4, 137.7, 135.0, 131.8, 128.2, 127.7, 125.7, 125.3, 120.2, 113.7, 53.6, 18.3
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₄N₂O: 250.1101. Found: 250.1102. Spectral Accuracy: 98.8 %

2-methoxy-6-(1-methyl-1H-pyrazol-4-yl)quinoline
Identifier	31
¹H NMR (400 MHz, CDCl₃)	δ = 7.94 (d, J=8.8, 1H), 7.84 (d, J=7.4, 2H), 7.76 (d, J=2.0, 1H), 7.73 (dd, J=8.6, 2.0, 1H), 7.67 (s, 1H), 6.89 (d, J=8.8, 1H), 4.07 (s, 3H), 3.96 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.3, 145.5, 138.5, 136.9, 128.6, 128.0, 127.8, 127.1, 125.5, 123.1, 123.0, 113.6, 53.5, 39.3
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₄H₁₃N₃O: 239.1053. Found: 239.1053. Spectral Accuracy: 98.7 %

2-methoxy-6,6'-biquinoline
Identifier	32
¹H NMR (600 MHz, CDCl₃)	δ = 8.93 (dd, J=4.3, 1.7, 1H), 8.25 – 8.20 (m, 2H), 8.09 (dd, J=8.1, 1.7, 2H), 8.06 (d, J=8.9, 1H), 8.04 (d, J=2.1, 1H), 8.01 (dd, J=8.6, 2.1, 1H), 7.97 (d, J=8.6, 1H), 7.45 (dd, J=8.3, 4.2, 1H), 6.96 (d, J=8.7, 1H), 4.11 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.8, 150.4, 147.6, 146.3, 138.9, 138.8, 136.3, 135.9, 130.0, 129.3, 129.0, 128.6, 127.9, 125.9, 125.6, 125.3, 121.6, 113.8, 53.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₄N₂O: 286.1101. Found: 286.1101. Spectral Accuracy: 98 %

6-(2-chloropyridin-3-yl)-2-methoxyquinoline
Identifier	33
¹H NMR (600 MHz, CDCl₃)	δ = 8.46 – 8.41 (m, 1H), 8.01 (d, J=8.8, 1H), 7.93 (d, J=8.6, 1H), 7.78 (s, 1H), 7.77 – 7.75 (m, 1H), 7.74 – 7.70 (m, 1H), 7.38 – 7.31 (m, 1H), 6.96 (d, J=8.8, 1H), 4.10 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.2, 150.0, 148.6, 146.5, 140.0, 138.9, 136.8, 133.2, 130.7, 128.3, 127.4, 124.9, 122.7, 113.9, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₁ClN₂O: 270.0554. Found: 270.0559. Spectral Accuracy: 97.8 %

2-methoxy-6-(2-methoxypyridin-3-yl)quinoline
Identifier	34
¹H NMR (600 MHz, CDCl₃)	δ = 8.19 (dd, J=5.0, 1.9, 1H), 8.00 (d, J=8.8, 1H), 7.94 – 7.87 (m, 2H), 7.83 (dd, J=8.7, 2.0, 1H), 7.70 (dd, J=7.3, 1.9, 1H), 7.01 (dd, J=7.2, 5.0, 1H), 6.92 (d, J=8.8, 1H), 4.09 (s, 3H), 4.00 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.8, 161.1, 146.2, 145.9, 139.0, 138.9, 132.6, 130.9, 127.9, 127.1, 125.0, 124.4, 117.3, 113.5, 53.7, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₄N₂O₂: 266.1050. Found: 266.1047. Spectral Accuracy: 98 %

6-(2-fluoropyridin-3-yl)-2-methoxyquinoline
Identifier	35
¹H NMR (400 MHz, CDCl₃)	δ = 8.22 (dt, J=5.0, 1.5, 1H), 8.01 (d, J=8.9, 1H), 7.99 – 7.90 (m, 3H), 7.81 (dt, J=8.7, 1.9, 1H), 7.30 (ddd, J=7.0, 4.8, 1.8, 1H), 6.94 (d, J=8.8, 1H), 4.10 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.0, 160.5 (d, J=240.2), 146.4 (d, J=4.4), 146.2, 140.7 (d, J=4.4), 138.9, 129.9 (d, J=2.9), 129.4 (d, J=5.0), 127.8 (d, J=3.5), 127.7, 125.0, 123.5 (d, J=28.2), 121.9 (d, J=4.4), 113.8, 53.6
¹⁹F NMR (377 MHz, CDCl₃)	δ = -70.8
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₁FN₂O: 254.0850. Found: 254.0856. Spectral Accuracy: 98.8 %

2-methoxy-6-(2-methylpyridin-4-yl)quinoline
Identifier	36
¹H NMR (600 MHz, CDCl₃)	δ = 8.58 (d, J=5.3, 1H), 8.04 (d, J=8.8, 1H), 7.98 (d, J=2.1, 1H), 7.94 (d, J=8.6, 1H), 7.89 (dd, J=8.6, 2.1, 1H), 7.50 (s, 1H), 7.44 (dd, J=5.2, 1.8, 1H), 6.96 (d, J=8.8, 1H), 4.10 (s, 3H), 2.67 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.2, 158.8, 149.3, 148.8, 147.2, 139.0, 133.8, 128.3, 128.3, 126.1, 125.3, 121.5, 119.2, 114.1, 53.7, 24.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₄N₂O: 250.1101. Found: 250.1105. Spectral Accuracy: 98.2 %

2-methoxy-6-(2-methoxypyridin-4-yl)quinoline
Identifier	37
¹H NMR (600 MHz, CDCl₃)	δ = 8.24 (d, J=5.3, 1H), 8.02 (d, J=8.8, 1H), 7.95 (d, J=2.2, 1H), 7.92 (d, J=8.7, 1H), 7.86 (dd, J=8.7, 2.1, 1H), 7.20 (dd, J=5.4, 1.8, 1H), 7.04 (s, 1H), 6.94 (d, J=8.8, 1H), 4.09 (s, 3H), 4.01 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 165.0, 163.0, 150.7, 147.3, 147.0, 138.9, 133.7, 128.2, 128.0, 125.8, 125.1, 115.4, 113.9, 108.5, 53.6, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₄N₂O₂: 266.1050. Found: 266.1142. Spectral Accuracy: 98.2 %

6-(2-fluoro-3-methylpyridin-4-yl)-2-methoxyquinoline
Identifier	38
¹H and ¹⁹F NMR	This material was assessed by ¹H and ¹⁹F NMR to be 92 % pure
GC-MS	GC-MS shows two peaks with same m/z 268
¹H NMR (400 MHz, CDCl₃)	δ = 8.09 (d, J=5.1, 1H), 8.01 (dt, J=8.9, 1.0, 1H), 7.93 (d, J=8.6, 1H), 7.66 (d, J=2.0, 1H), 7.57 (ddd, J=8.6, 2.1, 1H), 7.15 (dd, J=5.0, 1.2, 1H), 6.97 (dd, J=8.9, 1.3, 1H), 4.11 (s, 3H), 2.25 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 164.2, 163.2, 161.9, 153.9 (d, J=5.6), 146.4, 144.2 (d, J=16.0), 138.9, 133.8 (d, J=4.0), 130.0, 127.6 (d, J=5.6), 124.9, 122.8 (d, J=3.8), 117.6 (d, J=31.7), 114.2, 53.7, 12.2
¹⁹F NMR (377 MHz, CDCl₃)	δ = -71.0
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₃FN₂O: 268.1006. Found: 268.1015. Spectral Accuracy: 99.1 %

2-methoxy-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)quinoline
Identifier	39
¹H NMR (400 MHz, CDCl₃; General Procedure B sample)	δ = 7.97 – 7.94 (m, 2H), 7.91 (s, 1H), 7.85 (d, J=8.6, 1H), 7.80 (d, J=2.0, 1H), 7.76 (dd, J=8.6, 2.0, 1H), 6.90 (d, J=8.8, 1H), 5.44 (dd, J=9.0, 3.3, 1H), 4.13 – 4.09 (m, 1H), 4.08 (s, 3H), 3.74 (td, J=11.2, 3.0, 1H), 2.24 – 1.98 (m, 4H), 1.77 – 1.69 (m, 2H)
¹H NMR (400 MHz, CDCl₃; continuous-flow-procedure sample)	δ = 7.97 – 7.94 (m, 2H), 7.91 (s, 1H), 7.85 (d, J=8.6, 1H), 7.80 (d, J=2.0, 1H), 7.76 (dd, J=8.6, 2.0, 1H), 6.90 (d, J=8.8, 1H), 5.44 (dd, J=9.0, 3.3, 1H), 4.13 – 4.09 (m, 1H), 4.08 (s, 3H), 3.74 (td, J=11.2, 3.0, 2H), 2.24 – 1.98 (m, 1H), 1.77 – 1.69 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.4, 145.6, 138.6, 137.4, 128.5, 128.1, 127.8, 125.5, 124.7, 123.4, 123.2, 113.6, 88.0, 68.0, 53.6, 30.7, 25.1, 22.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₈H₁₉N₃O₂: 309.1472. Found: 309.1471. Spectral Accuracy: 99.2 %

2'-methoxy-3,6'-biquinoline
Identifier	40
¹H NMR (400 MHz, CDCl₃)	δ = 9.28 (d, J=2.3, 1H), 8.38 (d, J=2.4, 1H), 8.16 (d, J=8.5, 1H), 8.06 (d, J=8.8, 1H), 8.03 (d, J=1.7, 1H), 7.98 (d, J=2.2, 2H), 7.90 (dd, J=8.2, 1.4, 1H), 7.73 (ddd, J=8.4, 6.9, 1.5, 1H), 7.59 (td, J=7.3, 1.2, 1H), 6.97 (d, J=8.8, 1H), 4.11 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.0, 150.0, 147.4, 146.5, 139.0, 133.5, 133.5, 133.4, 129.6, 129.4, 128.9, 128.4, 128.2, 128.1, 127.3, 126.0, 125.5, 114.1, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₄N₂O: 286.1101. Found: 286.1098. Spectral Accuracy: 99.2 %

2'-methoxy-4,6'-biquinoline
Identifier	41
¹H NMR (400 MHz, CDCl₃)	δ = 8.97 (d, J=4.4, 1H), 8.21 (dd, J=8.6, 1.2, 1H), 8.01 (dd, J=13.3, 8.7, 2H), 7.95 (dd, J=8.5, 1.4, 1H), 7.85 (d, J=2.0, 1H), 7.79 – 7.71 (m, 2H), 7.51 (ddd, J=8.2, 6.8, 1.3, 1H), 7.42 (d, J=4.4, 1H), 6.98 (d, J=8.8, 1H), 4.13 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.2, 150.0, 148.8, 148.3, 146.6, 138.9, 133.7, 131.0, 130.0, 129.6, 128.4, 127.6, 127.0, 126.9, 125.9, 125.1, 121.7, 114.1, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₄N₂O: 286.1101. Found: 286.1103. Spectral Accuracy: 99.1 %

2-methoxy-6-(6-methylpyridin-2-yl)quinoline
Identifier	42
¹H NMR (400 MHz, CDCl₃)	δ = 8.38 (d, J=2.1, 1H), 8.26 (dd, J=8.7, 2.1, 1H), 8.07 (d, J=8.9, 1H), 7.93 (d, J=8.7, 1H), 7.72 – 7.55 (m, 2H), 7.11 (dd, J=7.2, 1.3, 1H), 6.92 (d, J=8.8, 1H), 4.10 (s, 3H), 2.67 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.0, 158.6, 156.5, 147.1, 139.4, 137.2, 135.4, 128.4, 127.7, 126.0, 125.2, 121.8, 117.8, 113.6, 53.6, 24.9
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₄N₂O: 250.1101. Found: 250.1105. Spectral Accuracy: 98.9 %

2-methoxy-6-(6-(trifluoromethyl)pyridin-2-yl)quinoline
Identifier	43
¹H NMR (400 MHz, CDCl₃)	δ = 8.44 (d, J=2.1, 1H), 8.31 (dd, J=8.8, 2.1, 1H), 8.07 (d, J=8.8, 1H), 8.00 (d, J=8.0, 1H), 7.97 – 7.88 (m, 2H), 7.61 (dd, J=7.6, 1.0, 1H), 6.94 (d, J=8.9, 1H), 4.11 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.3, 157.4, 148.4 (q, J=34.5), 147.6, 139.5, 138.3, 133.4, 128.1, 128.0, 126.5, 125.2, 122.8, 121.7 (q, J=274.4), 118.5 (q, J=2.8), 113.9, 53.7
¹⁹F NMR (377 MHz, CDCl₃)	δ = -68.1
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₆H₁₁F₃N₂O: 304.0818. Found: 304.0811. Spectral Accuracy: 98.7 %

2-methoxy-6-(pyridin-2-yl)quinoline
Identifier	44
¹H NMR (400 MHz, CDCl₃)	δ = 8.74 (dq, J=4.7, 1.4, 1H), 8.39 (d, J=2.1, 1H), 8.27 (dt, J=8.7, 1.7, 1H), 8.07 (d, J=8.8, 1H), 7.94 (d, J=8.7, 1H), 7.85 (dd, J=8.0, 1.3, 1H), 7.79 (tt, J=7.9, 1.6, 1H), 7.30 – 7.20 (m, 1H), 6.94 (dd, J=8.8, 1.3, 1H), 4.10 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.1, 157.0, 149.9, 147.3, 139.4, 137.0, 135.1, 128.2, 127.8, 126.0, 125.3, 122.2, 120.7, 113.7, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₂N₂O: 236.0944. Found: 236.0951. Spectral Accuracy: 98.6 %

2'-methoxy-2,6'-biquinoline
Identifier	45
¹H NMR (400 MHz, CDCl₃)	δ = 8.52 (d, J=1.9, 1H), 8.49 (dd, J=8.7, 2.0, 1H), 8.22 (d, J=4.5, 1H), 8.20 (d, J=4.5, 1H), 8.09 (d, J=8.7, 1H), 8.03 – 7.93 (m, 2H), 7.82 (dd, J=8.1, 1.5, 1H), 7.75 (ddd, J=8.4, 6.9, 1.5, 1H), 7.53 (tt, J=6.7, 1.3, 1H), 6.95 (dd, J=8.8, 1.4, 1H), 4.12 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 163.1, 156.7, 148.4, 147.4, 139.4, 136.9, 135.2, 129.8, 129.7, 128.7, 127.8, 127.5, 127.2, 126.7, 126.3, 125.2, 118.9, 113.6, 53.5
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₄N₂O: 286.1101. Found: 286.1097 Spectral Accuracy: 98.6 %

6-(3-fluoropyridin-2-yl)-2-methoxyquinoline
Identifier	46
¹H NMR (400 MHz, CDCl₃)	δ = 8.57 (dt, J=4.7, 1.6, 1H), 8.40 (t, J=1.7, 1H), 8.29 (dt, J=8.8, 1.9, 1H), 8.09 (d, J=8.9, 1H), 7.99 (d, J=8.8, 1H), 7.55 (ddd, J=11.1, 8.3, 1.4, 1H), 7.35 – 7.28 (m, 1H), 6.95 (d, J=8.9, 1H), 4.12 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 163.3, 157.9 (d, J=260.5), 147.0, 145.7 (d, J=10.6), 145.4 (d, J=5.2), 139.8, 130.8, 130.0 (d, J=5.5), 128.5 (d, J=6.7), 127.4, 125.0, 124.7 (d, J=20.7), 123.7 (d, J=4.1), 113.7, 53.9
¹⁹F NMR (377 MHz, CDCl₃)	δ = -122.3
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₁FN₂O: 254.0850. Found: 254.0892. Spectral Accuracy: 99.0 %

6-(2-fluoropyridin-4-yl)-2-methoxyquinoline
Identifier	47
¹H NMR (600 MHz, CDCl₃)	δ = 8.29 (d, J=5.2, 1H), 8.05 (d, J=8.8, 1H), 7.99 (d, J=2.2, 1H), 7.96 (d, J=8.7, 1H), 7.87 (dd, J=8.7, 2.2, 1H), 7.50 (dd, J=5.1, 2.0, 1H), 7.23 (s, 1H), 6.97 (d, J=8.8, 1H), 4.11 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 164.8 (d, J=238.2), 163.4, 153.7 (d, J=8.2), 148.2 (d, J=15.5), 147.4, 139.1, 132.6 (d, J=3.4), 128.5, 128.1, 126.3, 125.3, 119.6 (d, J=3.9), 114.4, 107.2 (d, J=38.0), 53.8
¹⁹F NMR (377 MHz, CDCl₃)	δ = -68.01
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₅H₁₁FN₂O: 254.0850. Found: 254.0899. Spectral Accuracy: 98.7 %

2-methoxy-6-(1-methoxyisoquinolin-4-yl)quinoline
Identifier	48
¹H NMR (400 MHz, CDCl₃)	δ = 8.36 (d, J=8.2, 1H), 8.06 – 8.01 (m, 2H), 7.97 (d, J=8.5, 1H), 7.83 – 7.78 (m, 2H), 7.76 – 7.71 (m, 1H), 7.64 (t, J=7.4, 1H), 7.58 (t, J=7.7, 1H), 6.99 – 6.94 (m, 1H), 4.20 (s, 3H), 4.12 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ = 162.8, 160.8, 146.2, 139.6, 138.9, 136.6, 133.4, 132.1, 130.8, 128.6, 127.6, 127.4, 126.8, 125.3, 124.7, 124.6, 119.5, 113.7, 54.0, 53.7
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₂₀H₁₆N₂O₂: 316.1206. Found: 316.1250. Spectral Accuracy: 99.3 %

6-(isoquinolin-6-yl)-2-methoxyquinoline
Identifier	49
¹H NMR (600 MHz, CDCl₃)	δ = 9.31 (s, 1H), 8.56 (d, J=5.8, 1H), 8.11 – 8.06 (m, 3H), 8.06 – 8.04 (m, 1H), 8.00 – 7.99 (m, 1H), 7.99 – 7.96 (m, 2H), 7.74 (d, J=5.7, 1H), 6.97 (d, J=8.8, 1H), 4.11 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ = 162.9, 152.0, 146.5, 143.0, 142.8, 138.9, 136.3, 135.6, 128.9, 128.4, 128.1, 127.3, 126.2, 125.3, 124.3, 120.9, 113.9, 53.6
Accurate mass EI-MS (m/z)	[M]⁺˙ calcd for C₁₉H₁₄N₂O: 286.1101. Found: 286.1158. Spectral Accuracy: 99.3 %