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[D6]acetone): δ = 10.35 (br, 1 H), 7.69 (d, J = 7.2 Hz, 2 H), 7.33–7.25
(m, 3 H), 7.14 (t, J = 7.4 Hz, 1 H), 7.08 (dt, J = 2.3, 0.8 Hz, 1 H), 6.73
(m, 1 H), 6.69 (dd, J = 2.2, 0.9 Hz, 1 H), 2.27 (s, 3 H). 13C NMR (75 MHz,
Acetone): δ = 138.39, 137.71, 133.31, 131.63, 129.22, 127.62, 127.47,
125.23, 121.77, 120.33, 111.43, 99.31, 21.35. HRMS (ESI) m/z calcu-
lated for C15H14N [M + H]+ 208. 1121, found 208. 1115.
124.47, 120.51, 110.73, 100.19, 21.60. HRMS (ESI) m/z calculated for
C15H13ClN [M + H]+ 242.0731, found 242.0721.
5-chloro-2-(4-chlorophenyl)-1H-indole (4cf): yellowish solid
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(128 mg, 98 % yield); m.p. 190–192 °C (lit.[28] 190–192 °C). H NMR
(500 MHz, CDCl3): δ = 8.23 (br, 1 H), 7.51–7.47 (m, 3 H), 7.36–7.32
(m, 2 H), 7.23 (d, J = 8.6 Hz, 1 H), 7.08 (dd, J = 8.6, 2.0 Hz, 1 H), 6.66
(d, J = 1.5 Hz, 1 H). 13C NMR (126 MHz, CDCl3): δ = 138.22, 135.34,
134.06, 130.52, 130.36, 129.46, 126.55, 126.20, 123.06, 120.22,
112.05, 100.16. HRMS (ESI) m/z calculated for C14H10Cl2N [M + H]+
262.0185, found 262.0180.
5-methyl-2-phenyl-1H-indole (4ad): white solid (101 mg, 98 %
yield); m.p. 210–212 °C (lit.[20] 211–213 °C). 1H NMR (300 MHz,
CDCl3): δ = 8.23 (br, 1 H), 7.69–7.63 (m, 2 H), 7.49–7.41 (m, 3 H),
7.36–7.28 (m, 2 H), 7.04 (dd, J = 8.3, 1.3 Hz, 1 H), 6.77 (dd, J = 2.1,
0.8 Hz, 1 H), 2.47 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 138.08,
135.30, 132.66, 129.69, 129.62, 129.12, 127.71, 125.20, 124.12,
2-(tert-butyl)-1H-indole (4ea): white solid (84 mg, 97 % yield); m.p.
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72–73 °C (lit.[29] 74–76 °C). H NMR (300 MHz, CDCl3): δ = 7.85 (br,
120.44, 110.68, 99.70, 21.60. HRMS (ESI) m/z calculated for C15H14
N
1 H), 7.48–7.44 (m, 1 H), 7.26–7.20 (m, 1 H), 7.08–6.94 (m, 2 H), 6.18
(dd, J = 2.3, 0.9 Hz, 1 H), 1.31 (s, 9 H). 13C NMR (75 MHz, CDCl3): δ =
148.90, 135.89, 128.65, 121.20, 120.11, 119.73, 110.48, 97.09, 31.96,
30.45. HRMS (ESI) m/z calculated for C12H16N [M + H]+ 174.1277,
found 174.1271.
[M + H]+ 208.1048, found 208.1050.
7-ethyl-2-phenyl-1H-indole (4ae): white solid (82 mg, 74 % yield);
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m.p. 52–54 °C (lit.[19] 53–54 °C). H NMR (300 MHz, CDCl3): δ = 8.13
(br, 1 H), 7.63–7.58 (m, 2 H), 7.40–7.33 (m, 3 H), 7.28–7.21 (m, 1 H),
7.04–6.93 (m, 2 H), 6.76 (d, J = 2.2 Hz, 1 H), 2.84 (q, J = 7.6 Hz, 2 H),
1.33 (t, J = 7.6 Hz, 3 H). 13C NMR (75 MHz, CDCl3): δ = 137.68, 135.82,
132.73, 129.15, 127.79, 126.41, 125.36, 121.04, 120.70, 118.57,
100.73, 24.19, 13.96. HRMS (ESI) m/z calculated for C16H16N [M +
H]+ 222.1277, found 222.1275.
2-(1-adamantyl)-1H-indole (4fa): yellowish solid (75 mg, 60 %
yield); m.p. 147–149 °C (lit.[30] 146–147 °C). 1H NMR (300 MHz,
CDCl3): δ = 7.91 (br, 1 H), 7.47 (d, J = 7.5 Hz, 1 H), 7.22 (d, J = 7.8 Hz,
1 H), 7.01 (tt, J = 7.0, 6.2 Hz, 2 H), 6.14 (d, J = 1.5 Hz, 1 H), 2.02 (s,
3 H), 1.89 (d, J = 2.2 Hz, 6 H), 1.78–1.65 (m, 7 H). 13C NMR (75 MHz,
CDCl3): δ = 149.37, 135.53, 128.55, 121.03, 120.10, 119.59, 110.53,
96.40, 42.67, 36.86, 33.80, 28.57. HRMS (ESI) m/z calculated for
5-chloro-2-phenyl-1H-indole (4af): white solid (109 mg, 96 %
yield); m.p. 198–200 °C (lit.[21] 199–200 °C). 1H NMR (300 MHz,
CDCl3): δ = 8.27 (br, 1 H), 7.61–7.49 (m, 3 H), 7.40–7.32 (m, 2 H),
7.29–7.20 (m, 2 H), 7.06 (dd, J = 8.6, 2.0 Hz, 1 H), 6.67 (dd, J = 2.0,
0.6 Hz, 1 H). 13C NMR (75 MHz, CDCl3): δ = 139.44, 135.27, 132.01,
130.47, 129.24, 128.26, 125.99, 125.38, 122.71, 120.12, 111.99, 99.70.
HRMS (ESI) m/z calculated for C14H11ClN [M + H]+ 228.0575, found
228.0562.
C
18H22N [M + H]+ 252.1747, found 252.1743.
2-phenethyl-1H-indole (4ga): white solid (46 mg, 42 % yield); m.p.
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118–120 °C (lit.[31] 118–120 °C). H NMR (300 MHz, CDCl3): δ = 7.65
(br, 1 H), 7.45 (dd, J = 7.9, 0.9 Hz, 1 H), 7.27–7.13 (m, 6 H), 7.01 (m,
2 H), 6.20 (d, J = 1.2 Hz, 1 H), 3.05–2.92 (m, 4 H). 13C NMR (75 MHz,
CDCl3): δ = 141.34, 139.14, 135.96, 128.82, 128.70, 128.56, 126.43,
121.25, 120.00, 119.78, 110.47, 99.98, 35.77, 30.28. HRMS (ESI) m/z
calculated for C16H16N [M + H]+ 222.1277, found 222.1275.
7-bromo-5-methyl-2-phenyl-1H-indole (4ag):[24] yellowish solid,
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(91 mg, 64 % yield); m.p. 83–85 °C. H NMR (300 MHz, CDCl3): δ =
8.24 (br, 1 H), 7.61–7.56 (m, 2 H), 7.40–7.33 (m, 2 H), 7.29–7.22 (m,
2 H), 7.10 (dd, J = 1.3, 0.5 Hz, 1 H), 6.71 (d, J = 2.3 Hz, 1 H), 2.34 (s,
3 H). 13C NMR (75 MHz, CDCl3): δ = 138.78, 133.98, 132.05, 131.24,
130.56, 129.20, 128.19, 126.09, 125.41, 119.70, 104.04, 100.62, 21.34.
HRSM (ESI) m/z calculated for C15H13NBr [M + H]+ 286.0226, found
286.0229.
2-octyl-1H-indole (4ha): white solid (45 mg, 39 % yield); m.p. 50–
51 °C (lit.[32] 50 °C). 1H NMR (500 MHz, CDCl3): δ = 7.75 (br, 1 H),
7.45 (d, J = 7.7 Hz, 1 H), 7.20 (d, J = 7.7 Hz, 1 H), 7.01 (m, 2 H), 6.15
(d, J = 0.9 Hz, 1 H), 2.66 (t, J = 7.6 Hz, 2 H), 1.67–1.60 (m, 2 H), 1.34–
1.17 (m, 10 H), 0.81 (t, J = 6.9 Hz, 3 H) 13C NMR (126 MHz, CDCl3):
δ = 140.17, 135.96, 129.02, 121.03, 119.87, 119.70, 110.39, 99.59,
32.01, 29.55, 29.49, 29.37, 29.35, 28.43, 22.81, 14.24. HRMS (ESI) m/z
calculated for C16H24N [M + H]+ 230.1903, found 230.1903.
5-methyl-2-(4-methoxyphenyl)-1H-indole (4bd): white solid
(96 mg, 81 % yield); m.p. 220 °C (lit.[25] 220–221 °C). 1H NMR
(300 MHz, DMSO): δ = 11.30 (br, 1 H), 7.81–7.74 (m, 2 H), 7.29–7.23
(m, 2 H), 7.05–6.99 (m, 2 H), 6.89 (dd, J = 8.3, 1.3 Hz, 1 H), 6.65 (d,
J = 1.4 Hz, 1 H), 3.80 (s, 3 H), 2.36 (s, 3 H). 13C NMR (75 MHz, DMSO):
δ = 159.03, 138.12, 135.66, 129.46, 127.93, 126.60, 125.41, 122.97,
119.66, 114.66, 111.14, 97.22, 55.53, 21.59. HRMS (ESI) m/z calcu-
lated for C16H16NO [M + H]+ 238.1226, found 238.1227.
2-decyl-1H-indole (4ia):[33] white solid (67 mg, 52 % yield); m.p.
48–50 °C. 1H NMR (300 MHz, CDCl3): δ = 7.75 (br, 1 H), 7.47–7.43
(m, 1 H), 7.23–7.19 (m, 1 H), 7.01 (m, 2 H), 6.16 (dd, J = 2.0, 0.9 Hz,
1 H), 2.67 (t, J = 7.6 Hz, 2 H), 1.64 (dt, J = 15.1, 7.7 Hz, 2 H), 1.33–
1.16 (m, 14 H), 0.81 (t, J = 6.7 Hz, 3 H). 13C NMR (75 MHz, CDCl3):
δ = 140.16, 135.95, 129.01, 121.04, 119.87, 119.70, 110.38, 99.60,
32.04, 29.75, 29.71, 29.59, 29.48, 29.35, 28.43, 22.83, 14.26. HRMS
(ESI) m/z calculated for C18H28N [M + H]+ 258.2216, found 258.2218.
5-chloro-2-(4-methoxyphenyl)-1H-indole (4bf):[26] yellowish solid
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(121 mg, 94 % yield); m.p. 236–238 °C. H NMR (300 MHz, DMSO):
δ = 8.33 (br, 1 H), 7.86–7.80 (m, 2 H), 7.51 (d, J = 2.0 Hz, 1 H), 7.39
(d, J = 8.6 Hz, 1 H), 7.05–6.99 (m, 3 H), 6.74 (d, J = 0.7 Hz, 1 H), 3.80
(s, 3 H). 13C NMR (75 MHz, DMSO): δ = 159.03, 139.65, 135.54,
130.00, 126.62, 124.48, 123.61, 120.70, 118.59, 114.35, 112.59, 96.87,
55.19. HRMS (ESI) m/z calculated for C15H13ClNO [M + H]+ 258.0680,
found 258.0666.
2-(tert-butyl)-5-methyl-1H-indole (4ed): white solid (85 mg, 91 %
yield); m.p. 102–104 °C (lit.[29] 101–103 °C);.1H NMR (300 MHz,
CDCl3): δ = 7.72 (br, 1 H), 7.24 (td, J = 1.5, 0.7 Hz, 1 H), 7.10 (d, J =
8.2 Hz, 1 H), 6.88–6.83 (m, 1 H), 6.08 (dd, J = 2.2, 0.9 Hz, 1 H), 2.34
(s, 3 H), 1.29 (s, 9 H). 13C NMR (75 MHz, CDCl3): δ = 149.03, 134.18,
128.94, 128.85, 122.66, 119.83, 110.12, 96.60, 31.94, 30.43, 21.57.
HRMS (ESI) m/z calculated for C13H18N [M + H]+ 188.1434, found
188.1426.
2-(4-chlorophenyl)-5-methyl-1H-indole (4cd): white solid
(118 mg, 98 %); m.p. 251–253 °C (lit.[27] 252–253 °C). 1H NMR
(500 MHz, CDCl3): δ = 8.11 (br, 1 H), 7.52–7.47 (m, 2 H), 7.35–7.30
(m, 3 H), 7.21 (d, J = 8.3 Hz, 1 H), 6.96 (dd, J = 8.3, 1.2 Hz, 1 H), 6.65
2-(tert-butyl)-5-chloro-1H-indole (4ef): white solid (98 mg, 95 %
yield); a m.p. 64–66 °C (lit.[28] 62–66 °C);.1H NMR (300 MHz, CDCl3):
(d, J = 1.3 Hz, 1 H), 2.37 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = δ = 7.85 (br, H), 7.40 (d, J = 2.0, Hz, 1 H), 7.16–7.08 (m, 1 H), 6.97
136.89, 135.41, 133.43, 131.20, 129.86, 129.61, 129.32, 126.37,
(dd, J = 8.6, 2.0 Hz, 1 H), 6.11 (dd, J = 2.2, 0.7 Hz, 1 H), 1.29 (s, 9 H).
Eur. J. Org. Chem. 0000, 0–0
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© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim