Molecules 2018, 23, 3317
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128.7, 126.6, 125.9, 122.1, 120.1, 119.6, 119.2, 115.5, 109.6, 32.8; LRMS (EI, 70 Ev) m/z (%): 287 (M+, 100),
285 (M+, 100).
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3-(4-Chlorophenyl)-1-methyl-1H-indole (10). Light brown solid. 76% yield (110 mg). M.P.: 97–99 C.
1H-NMR (500 MHz, CDCl3)
δ 7.90 (d, J = 8.0 Hz, 1H), 7.67–7.53 (m, 2H), 7.45–7.35 (m, 3H), 7.33–7.29
(m, 1H), 7.25–7.19 (m, 2H), 3.84 (s, 3H). 13C-NMR (126 MHz, CDCl3)
δ 137.5, 134.1, 131.2, 128.8, 128.4,
126.6, 125.9, 122.1, 120.1, 119.6, 115.5, 109.6, 32.9; LRMS (EI, 70 Ev) m/z (%): 241 (M+, 100).
1-Methyl-3-(3-nitrophenyl)-1H-indole (11). Orange solid. 56% yield (85 mg). M.P.: 108–109 ◦C. 1H-NMR
(500 MHz, CDCl3)
δ 8.49 (t, J = 2.0 Hz, 1H), 8.08 (ddd, J = 8.2, 2.3, 1.1 Hz, 1H), 7.98 (dd, J = 7.8, 1.4 Hz,
1H), 7.94 (d, J = 7.9 Hz, 1H), 7.57 (t, J = 7.9 Hz, 1H), 7.41 (d, J = 8.2 Hz, 1H), 7.38–7.30 (m, 2H), 7.26 (t,
J = 7.5 Hz, 2H), 3.87 (s, 2H). 13C-NMR (126 MHz, CDCl3)
δ 148.7, 137.5, 137.5, 132.6, 129.5, 127.4, 125.6,
122.5, 121.4, 120.6, 120.1, 119.3, 114.3, 109.8, 33.0; LRMS (EI, 70 Ev) m/z (%): 252 (M+, 100); HRMS (ESI)
for C15H13N2O2 (M + H+): calcd. 253.0899, found 253.0894.
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3-(1-Methyl-1H-indol-3-yl)benzonitrile (12). Yellow solid. 61% yield (85 mg). M.P.: 121–124 C. 1H-NMR
(500 MHz, CDCl3) 7.98–7.80 (m, 3H), 7.58–7.46 (m, 2H), 7.40 (d, J = 8.2 Hz, 1H), 7.36–7.30 (m, 1H),
δ
7.29–7.18 (m, 2H), 3.86 (s, 3H). 13C-NMR (126 MHz, CDCl3)
δ 137.5, 137.0, 131.2, 130.3, 129.5, 128.8,
127.1, 125.6, 122.4, 120.5, 119.3, 119.1, 114.4, 112.8, 109.8, 33.0; LRMS (EI, 70 Ev) m/z (%): 232 (M+, 100);
HRMS (ESI) for C16H13N2 (M + H+): calcd. 232.2860, found 232.2868.
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3-(3,4-Dimethoxyphenyl)-1-methyl-1H-indole (13). Yellow oil. 76% yield (122 mg). H-NMR (500 MHz,
DMSO-d6)
δ 7.86 (d, J = 8.0 Hz, 1H), 7.60 (s, 1H), 7.47 (d, J = 8.3 Hz, 1H), 7.26–7.15 (m, 3H), 7.15–7.10
(m, 1H), 7.01 (d, J = 8.2 Hz, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.78 (s, 3H). 13C-NMR (126 MHz, DMSO-d6)
δ
149.5, 147.4, 137.6, 128.8, 127.5, 125.9, 121.8, 120.0, 119.7, 119.0, 115.4, 113.0, 111.1, 110.5, 56.1, 55.9, 32.9;
LRMS (EI, 70 Ev) m/z (%): 267 (M+, 100); HRMS (ESI) for C18H18NO2 (M + H+): calcd. 268.1332, found
268.1335.
3-(3,4-Difluorophenyl)-1-methyl-1H-indole (14) [27]. Yellow oil. 73% yield (106 mg).1H-NMR (500 MHz,
CDCl3)
δ
7.87 (d, J = 8.0 Hz, 1H), 7.48–7.40 (m, 1H), 7.38 (d, J = 8.2 Hz, 1H), 7.36–7.28 (m, 2H), 7.25–7.17
151.5 (d, J = 12.8 Hz), 149.6 (t, J = 13.0 Hz), 147.7 (d,
(m, 3H), 3.85 (s, 3H). 13C-NMR (126 MHz, CDCl3)
δ
J = 12.8 Hz), 137.4, 132.8 (dd, J = 6.6, 3.8 Hz), 126.7, 125.8, 122.9 (dd, J = 5.8, 3.3 Hz), 122.3, 120.2, 119.4,
117.4 (d, J = 17.4 Hz), 115.8 (d, J = 17.4 Hz), 114.9, 109.7, 32.9; LRMS (EI, 70 Ev) m/z (%): 243 (M+, 100).
1-Methyl-3-(naphthalen-2-yl)-1H-indole (15). Colorless oil. 82% yield (126 mg). 1H-NMR (500 MHz,
CDCl3)
δ 8.20 (s, 1H), 8.17 (d, J = 7.9 Hz, 1H), 8.00–7.90 (m, 3H), 7.87 (dd, J = 8.5, 1.7 Hz, 1H), 7.60–7.49
(m, 2H), 7.44 (d, J = 8.1 Hz, 1H), 7.42–7.37 (m, 1H), 7.36 (s, 1H), 7.35–7.31 (m, 1H), 3.85 (s, 3H). 13C-NMR
(126 MHz, CDCl3)
δ 137.5, 134.0, 133.1, 131.9, 128.2, 127.7, 127.6, 126.9, 126.4, 126.2, 126.0, 125.0, 124.8,
122.0, 120.0, 120.0, 116.5, 109.6, 32.8; LRMS (EI, 70 Ev) m/z (%): 257 (M+, 100).
3-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-1-methyl-1H-indole (16). Yellow oil. 55% yield (92 mg).
1H-NMR (500 MHz, CDCl3) δ 7.98 (dd, J = 8.0, 1.0 Hz, 1H), 7.39 (d, J = 8.3 Hz, 1H), 7.35 (d, J = 2.2 Hz,
1H), 7.34–7.30 (m, 1H), 7.28 (dd, J = 8.5, 1.8 Hz, 1H), 7.27–7.20 (m, 1H), 7.21 (s, 1H), 7.11 (d, J = 8.1 Hz,
1H), 4.31 (dt, J = 10.9, 5.6 Hz, 4H), 3.84 (s, 3H), 2.34–2.17 (m, 2H). 13C-NMR (126 MHz, CDCl3)
δ 151.3,
149.3, 137.3, 131.2, 126.2, 126.0, 122.1, 121.8, 121.8, 120.1, 119.8, 119.7, 115.8, 109.4, 70.6, 70.5, 32.7, 32.0;
LRMS (EI, 70 Ev) m/z (%): 279 (M+, 100); HRMS (ESI) for C18H18NO2 (M + H+): calcd. 280.1259, found
280.1263.
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3-(Benzofuran-2-yl)-1-methyl-1H-indole (17) [27]. Yellow oil. 47% yield (70 mg). H-NMR (500 MHz,
CDCl3)
δ
8.06 (d, J = 7.8 Hz, 1H), 7.61 (s, 1H), 7.60–7.55 (m, 1H), 7.54–7.49 (m, 1H), 7.39 (d, J = 7.9 Hz,
153.8,
1H), 7.37–7.27 (m, 2H), 7.27–7.20 (m, 2H), 6.91 (s, 1H), 3.85 (s, 3H). 13C-NMR (126 MHz, CDCl3)
δ
152.9, 137.4, 129.9, 127.5, 125.0, 123.0, 122.6, 122.5, 120.6, 120.3, 120.0, 110.5, 109.7, 106.9, 99.0, 33.0;
LRMS (EI, 70 Ev) m/z (%): 247 (M+, 100).