562 JOURNAL OF CHEMICAL RESEARCH 2018
1H); 13C NMR (100 MHz, CDCl3): δ 143.6, 141.3, 139.1, 137.3, 132.8,
128.8, 128.6, 128.4, 128.3, 128.1, 127.5, 125.9, 122.3, 120.7, 120.5,
113.8, 111.5, 103.7.
13C NMR (100 MHz, CDCl3): δ 143.8, 142.2, 138.0, 135.9, 134.8, 128.8,
128.1, 127.2, 121.3, 120.1, 119.8, 114.1, 110.3, 98.1, 8.2, 7.8; HRMS
calcd for C19H1635ClN+: [M+]: 293.0971; found: 293.0976.
2-Phenyl-1-(1-p-tolylvinyl)-1H-indole (3b):31 Oil; 1H NMR
(400 MHz, CDCl3): δ 7.68–7.62 (m, 1H), 7.51–7.46 (m, 2H), 7.28–7.18
(m, 3H), 7.18–7.06 (m, 5H), 7.04 (d, J = 8.2 Hz, 2H), 6.77 (s, 1H),
5.84 (s, 1H), 5.16 (s, 1H), 2.29 (s, 3H); 13C NMR (100 MHz, CDCl3):
δ 143.5, 141.3, 139.1, 138.8, 134.4, 132.8, 129.3, 128.9, 128.4, 128.1,
127.4, 125.8, 122.2, 120.5, 120.4, 113.0, 111.6, 103.6, 21.2.
2-(4-Chlorophenyl)-1-(1-phenylvinyl)-1H-indole (3l): Green solid;
1
m.p. 77–79 °C (lit.45 123–124 °C); H NMR (400 MHz, CDCl3): δ
7.66 (d, J = 7.6 Hz, 1H), 7.40 (d, J = 8.4 Hz, 2H), 7.24–7.20 (m, 4H),
7.19–7.09 (m, 6H), 6.76 (s, 1H), 5.92 (s, 1H), 5.28 (s, 1H); 13C NMR
(100 MHz, CDCl3): δ 143.5, 139.9, 139.2, 137.1, 133.4, 131.3, 129.5,
129.0, 128.6, 128.4, 128.2, 125.8, 122.6, 120.8, 120.6, 113.9, 111.5,
104.0.
1-[1-(4-Methoxyphenyl)vinyl]-2-phenyl-1H-indole
(3c):31
Oil;
1H NMR (400 MHz, CDCl3): δ 7.66 (d, J = 7.0 Hz, 1H), 7.51–7.46 (m,
2H), 7.28–7.21 (m, 3H), 7.16–7.10 (m, 5H), 6.76 (d, J = 8.4 Hz, 2H),
6.74 (s, 1H), 5.78 (s, 1H), 5.13 (s, 1H), 3.75 (s, 3H); 13C NMR (100
MHz, CDCl3): δ 160.1, 143.1, 141.3, 139.1, 132.8, 130.9, 128.9, 128.3,
128.1, 127.4, 127.3, 122.2, 120.5, 120.4, 114.0, 111.9, 111.5, 103.5, 55.2.
1-[1-(4-Chlorophenyl)vinyl]-2-phenyl-1H-indole (3d):Oil; 1H NMR
(400 MHz, CDCl3): δ 7.67 (d, J = 6.8 Hz, 1H), 7.45 (d, J = 6.8 Hz,
2H), 7.27–7.23 (m, 3H), 7.19–7.12 (m, 5H), 7.06 (d, J = 8.4 Hz, 2H),
6.77 (s, 1H), 5.89 (s, 1H), 5.31 (s, 1H); 13C NMR (100 MHz, CDCl3):
δ 142.7, 141.2, 139.0, 135.8, 134.7, 132.6, 128.8, 128.4, 128.3, 128.2,
127.6, 127.2, 122.4, 120.8, 120.6, 114.2, 111.3, 103.9; HRMS calcd for
C22H1635ClN+: [M+]: 329.0971; found: 329.0980.
1-[1-(4-Fluorophenyl)vinyl]-2-phenyl-1H-indole (3e):31 Oil; 1H NMR
(400 MHz, CDCl3): δ 7.67 (d, J = 7.4 Hz, 1H), 7.46 (d, J = 7.8 Hz,
2H), 7.28–7.24 (m, 3H), 7.19–7.15 (m, 3H), 7.12–7.06 (m, 2H), 6.88 (t,
J = 8.0 Hz, 2H), 6.76 (s, 1H), 5.84 (s, 1H), 5.29 (s, 1H); 13C NMR (100
MHz, CDCl3): δ 163.0 (d, 1JC–F = 247.4 Hz), 142.8, 141.2, 139.0, 133.5 (d,
4JC–F = 2.9 Hz), 132.7, 130.9, 128.3, 128.1, 127.7 (d, 3JC–F = 8.3 Hz), 127.5,
122.3, 120.8, 120.6, 115.5 (d, 2JC–F = 21.7 Hz), 113.4, 111.3, 103.8.
1-[1-(2-Chlorophenyl)vinyl]-2-phenyl-1H-indole (3f): Oil; 1H NMR
(400 MHz, CDCl3): δ 7.66–7.64 (m, 1H), 7.44–7.40 (m, 3H), 7.25–7.17
(m, 6H), 7.05–7.00 (m, 1H), 6.96–6.92 (m, 1H), 6.75–6.72 (m, 1H),
6.67 (s, 1H), 5.91 (s, 1H), 5.74 (s, 1H); 13C NMR (100 MHz, CDCl3):
δ 140.7, 140.4, 139.0, 136.1, 133.0, 132.2, 130.3, 129.2, 128.6, 128.5,
128.0, 127.4, 126.5, 122.4, 120.8, 120.6, 117.1, 111.2, 104.2; HRMS
calcd for C22H1635ClN+: [M+]: 329.0971; found: 329.0965.
1-(1-Cyclopropylvinyl)-2-phenyl-1H-indole (3g): Oil; 1H NMR
(400 MHz, CDCl3): δ 7.66 (d, J = 7.8 Hz, 2H), 7.61 (d, J = 7.4 Hz, 1H),
7.43–7.38 (m, 3H), 7.34 (d, J = 7.2 Hz, 1H), 7.20 (t, J = 7.6 Hz, 1H), 7.13
(t, J = 7.4 Hz, 1H), 6.69 (s, 1H), 5.33 (s, 1H), 5.24 (s, 1H), 1.34–1.28
(m, 1H), 0.54–0.52 (m, 2H), 0.41–0.38 (m, 2H); 13C NMR (100 MHz,
CDCl3): δ 147.0, 140.1, 138.8, 133.5, 132.2, 128.5, 128.3, 128.2, 127.6,
122.1, 120.3, 111.0, 110.9, 103.1, 16.4, 7.8; HRMS calcd for C19H17N+:
[M+]: 259.1361; found: 259.1357.
2-Butyl-1-(1-phenylvinyl)-1H-indole (3h):31 Oil; 1H NMR
(400 MHz, CDCl3): δ 7.57 (d, J = 7.6 Hz, 1H), 7.31–7.27 (m, 3H),
7.16–7.10 (m, 3H), 7.07 (t, J = 7.4 Hz, 2H), 6.39 (s, 1H), 6.06 (s, 1H),
5.42 (s, 1H), 2.51 (t, J = 7.4 Hz, 2H), 1.63–1.58 (m, 2H), 1.34–1.28 (m,
2H), 0.84 (t, J = 7.4 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 143.0,
141.9, 138.0, 137.1, 128.9, 128.7, 128.2, 125.7, 121.0, 119.9, 119.6, 113.7,
110.5, 100.4, 30.71, 26.7, 22.3, 13.8.
2-Cyclohexyl-1-(1-phenylvinyl)-1H-indole (3i): Oil; 1H NMR
(400 MHz, CDCl3): δ 7.56 (d, J = 7.4 Hz, 1H), 7.34 (d, J = 7.4 Hz, 1H),
7.29–7.23 (m, 3H), 7.12 (d, J = 6.8 Hz, 2H), 7.06 (t, J = 7.4 Hz, 2H),
6.42 (s, 1H), 6.09 (s, 1H), 5.45 (s, 1H), 2.97–2.77 (m, 1H), 1.98–1.41 (m,
10H); 13C NMR (100 MHz, CDCl3): δ 146.6, 143.2, 138.0, 137.1, 128.9,
128.7, 128.5, 125.6, 121.1, 119.9, 119.7, 114.1, 110.4, 98.1, 37.5, 33.6,
29.7, 25.3; HRMS calcd for C22H23N+: [M+]: 301.1830; found: 301.1819.
2-Cyclopropyl-1-(1-phenylvinyl)-1H-indole (3j):45 Oil; 1H NMR
(400 MHz, CDCl3): δ 7.54–7.52 (m, 1H), 7.31–7.27 (m, 3H), 7.19–7.16
(m, 2H), 7.15–7.12 (m, 1H), 7.09–7.03 (m, 2H), 6.19 (s, 1H), 6.05 (s,
1H), 5.49 (s, 1H), 1.67–1.60 (m, 1H), 0.79–0.71 (m, 2H), 0.70–0.63 (m,
2H); 13C NMR (100 MHz, CDCl3): δ 144.0, 143.2, 138.1, 137.4, 128.8,
128.6, 128.0, 125.9, 121.1, 120.0, 119.7, 113.6, 110.4, 97.7, 8.2, 7.8.
1-[1-(4-Chlorophenyl)vinyl]-2-cyclopropyl-1H-indole (3k): Oil;
1H NMR (400 MHz, CDCl3): δ 7.54–7.52 (m, 1H), 7.26 (d, J = 8.0 Hz,
2H), 7.12–7.09 (m, 2H), 7.08–7.05 (m, 3H), 6.19 (s, 1H), 6.04 (s, 1H),
5.50 (s, 1H), 1.64–1.60 (m, 1H), 0.79–0.74 (m, 2H), 0.70–0.62 (m, 2H);
2-(4-Chlorophenyl)-1-[1-(4-chlorophenyl)vinyl]-1H-indole (3m):
Oil; H NMR (400 MHz, CDCl3): δ 7.70–7.64 (m, 1H), 7.41–7.36
1
(m, 2H), 7.25–7.22 (m, 2H), 7.21–7.19 (m, 1H), 7.18–7.15 (m, 4H),
7.06–7.02 (m, 2H), 6.76 (s, 1H), 5.92 (s, 1H), 5.33 (s, 1H); 13C NMR
(100 MHz, CDCl3): δ 142.5, 139.8, 139.0, 135.5, 134.9, 133.6, 131.1,
129.4, 128.9, 128.5, 128.2, 127.1, 122.7, 121.0, 120.7, 114.4, 111.3,
104.2; HRMS calcd for C22H1535Cl2NNa+: [M + Na]+: 386.0479; found:
386.0468.
1
5-Chloro-2-phenyl-1-(1-phenylvinyl)-1H-indole (3n): Oil; H NMR
(400 MHz, CDCl3): δ 7.62 (s, 1H), 7.47–7.44 (m, 2H), 7.28–7.19
(m, 6H), 7.13–7.11 (m, 2H), 7.07–7.03 (m, 2H), 6.69 (s, 1H), 5.90 (s,
1H), 5.25 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 143.4, 142.6, 137.4,
136.9, 132.3, 129.3, 129.0, 128.7, 128.4, 128.2, 127.8, 126.3, 125.8,
122.5, 119.8, 114.1, 112.5, 103.1.; HRMS calcd for C22H1635ClN+: [M+]:
329.0971; found: 329.0962.
1
5-Chloro-2-phenyl-1-(1-p-tolylvinyl)-1H-indole (3o): Oil; H NMR
(400 MHz, CDCl3): δ 7.61 (s, 1H), 7.47 (d, J = 6.4 Hz, 2H), 7.28–7.21
(m, 3H), 7.04–7.02 (m, 6H), 6.69 (s, 1H), 5.84 (s, 1H), 5.15 (s, 1H),
2.29 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 143.2, 142.6, 139.1, 137.4,
134.0, 132.3, 129.4, 129.3, 128.4, 128.2, 127.8, 126.2, 125.7, 122.4,
119.8, 113.3, 112.6, 103.0, 21.2; HRMS calcd for C23H1835ClN+: [M+]:
343.1128; found: 343.1140.
5-Chloro-1-[1-(4-methoxyphenyl)vinyl]-2-phenyl-1H-indole (3p):
1
Oil; H NMR (400 MHz, CDCl3): δ 7.61 (s, 1H), 7.47 (d, J = 6.6 Hz,
2H), 7.29–7.22 (m, 3H), 7.11–7.00 (m, 4H), 6.75 (d, J = 8.8 Hz, 2H),
6.69 (s, 1H), 5.78 (s, 1H), 5.12 (s, 1H), 3.75 (s, 3H); 13C NMR (100
MHz, CDCl3): δ 160.3, 143.0, 142.6, 137.5, 132.4, 129.5, 129.3, 128.4,
128.1, 127.7, 127.2, 126.2, 122.4, 119.8, 114.1, 112.5, 112.1, 102.9,
55.2; HRMS calcd for C23H1835ClNNaO+: [M + Na]+: 382.0975; found:
382.0973.
1
5-Bromo-2-phenyl-1-(1-phenylvinyl)-1H-indole (3q): Oil; H NMR
(400 MHz, CDCl3): δ 7.78 (s, 1H), 7.47–7.43 (m, 2H), 7.29–7.17
(m, 6H), 7.14–6.97 (m, 4H), 6.69 (s, 1H), 5.89 (s, 1H), 5.25 (s, 1H);
13C NMR (100 MHz, CDCl3): δ 143.3, 142.4, 137.7, 136.8, 132.2, 130.0,
129.0, 128.7, 128.5, 128.2, 127.8, 125.8, 125.1, 122.9, 114.1, 113.8,
112.9, 103.0; HRMS calcd for C22H1679BrNNa+: [M + Na]+: 396.0364;
found: 396.0371.
5-Bromo-1-[1-(4-chlorophenyl)vinyl]-2-phenyl-1H-indole (3r): Oil;
1H NMR (400 MHz, CDCl3): δ 7.78 (s, 1H), 7.43–7.41 (m, 2H), 7.28–7.16
(m, 6H), 7.03–7.00 (m, 3H), 6.69 (s, 1H), 5.89 (s, 1H), 5.31 (s, 1H);
13C NMR (100 MHz, CDCl3): δ 141.3, 141.2, 136.5, 134.3, 133.8, 131.0,
128.9, 127.8, 127.3, 127.2, 126.9, 126.0, 124.1, 122.0, 113.5, 112.9, 111.6,
102.1; HRMS calcd for C22H1579Br35ClNNa+: [M + Na]+: 429.9974; found:
429.9971.
1
5-Bromo-2-phenyl-1-(1-p-tolylvinyl)-1H-indole (3s): Oil; H NMR
(400 MHz, CDCl3): δ 7.78 (s, 1H), 7.48–7.46 (m, 2H), 7.27–7.24 (m,
3H), 7.18–7.14 (m, 1H), 7.08–7.02 (m, 4H), 6.97 (d, J = 8.6 Hz, 1H),
6.70 (s, 1H), 5.85 (s, 1H), 5.16 (s, 1H), 2.30 (s, 3H); 13C NMR (100
MHz, CDCl3): δ 143.2, 142.4, 139.1, 137.7, 134.0, 132.2, 129.9, 129.4,
128.4, 128.2, 127.8, 125.7, 125.0, 122.9, 113.8, 113.3, 113.0, 102.8,
21.2; HRMS calcd for C23H1879BrNNa+: [M + Na]+: 410.0520; found:
410.0515.
5-Bromo-1-[1-(naphthalen-1-yl)vinyl]-2-phenyl-1H-indole
(3t):
Beige solid; m.p. 159–161 °C; 1H NMR (400 MHz, CDCl3): δ 7.86 (d,
J = 8.6 Hz, 1H), 7.77 (d, J = 1.6 Hz, 1H), 7.73 (d, J = 8.2 Hz, 1H), 7.64
(d, J = 8.2 Hz, 1H), 7.40–7.37 (m, 1H), 7.35–7.30 (m, 1H), 7.29–7.24
(m, 3H), 7.24–7.20 (m, 1H), 7.16 (t, J = 7.6 Hz, 1H), 7.12–7.04 (m, 3H),
7.02–6.97 (m, 1H), 6.57 (s, 1H), 5.78 (s, 1H), 5.68 (s, 1H); 13C NMR