Molecules 2019, 24, 1145
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3-Methyl-N-(pyrimidin-2-yl)indole (3ag) [46]: White solid (165.3 mg, 79 %); 1H-NMR (400 MHz, CDCl3)
δ
8.77 (d, J = 9.0 Hz, 1H), 8.66 (d, J = 4.8 Hz, 2H), 8.03 (s, 1H), 7.56 (d, J = 8.4 Hz, 1H), 7.42–7.19 (m, 2H),
6.98 (t, J = 4.8 Hz, 1H), 2.35 (s, 3H); 13C-NMR (100 MHz, CDCl3)
δ
158.0, 157.7, 135.7, 132.1, 123.7, 122.9,
121.8, 118.8, 116.3, 116.0, 115.5, 9.8; GC-MS m/z: 209 (M+).
1
2-(3-Methyl-indol-1-yl)benzamide (3ah) [47]: White waxy oil (140.1 mg, 56%); H-NMR (400 MHz,
DMSO-d6)
(100 MHz, DMSO-d6)
118.6, 111.0, 110.2. 9.5; GC-MS m/z: 250 (M+).
δ
7.67–7.53 (m, 4H), 7.50–7.41 (m, 2H), 7.32 (s, 1H), 7.19–7.05 (m, 4H), 2.29 (s, 3H); 13C-NMR
168.8, 165.0, 136.5, 135.9, 134.8, 130.4, 128.8, 127.3, 127.1, 126.9, 121.8, 119.3,
δ
◦
N-(2-Chloro-4-nitrophenyl)-3-methylindole (3ai): Orange solid (249.4 mg, 87%); mp 125~130 C; 1H-NMR
(600 MHz, CDCl3) 8.49 (s, 1H), 8.24 (d, J = 8.7 Hz, 1H), 7.65 (d, J = 7.3 Hz, 1H), 7.62 (d, J = 8.7 Hz,
1H), 7.27–7.19 (m, 4H), 7.11 (s, 1H), 2.41 (s, 3H); 13C-NMR (125 MHz, CDCl3)
146.2, 142.8, 136.4,
δ
δ
131.3, 129.8, 128.8, 126.8, 125.5, 123.1, 122.9, 120.9, 119.6, 114.6, 110.6, 9.7; HRMS (ESI): m/z Calcd. For:
C15H11ClNO2 [M + H]+: 287.0582; found 287.0576.
1
N-(2-Bromophenyl)-3-methylindole (3am) [48]: White waxy oil (214.6 mg, 75%); H-NMR (400 MHz,
CDCl3)
2H), 7.17–7.10 (m, 1H), 7.07 (s, 1H), 2.46 (s, 3H); 13C-NMR (100 MHz, CDCl3)
129.2, 129.0, 129.3, 122.3, 121.8, 119.7, 119.1, 112.5, 110.6, 9.8; GC-MS m/z: 287 (M+).
δ
7.80 (d, J = 7.9 Hz, 1H), 7.70–7.64 (m, 1H), 7.50–7.40 (m, 2H), 7.37–7.29 (m, 1H), 7.28–7.19 (m,
δ
138.8, 137.1, 134.0, 129.8,
◦
N-(3-Bromo-5-chlorophenyl)-3-methylindole (3an): White solid (221.2 mg, 69 %); mp 142~144 C; 1H-NMR
(400 MHz, CDCl3) 7.62 (d, J = 8.4 Hz, 1H), 7.57–7.55 (m, 2H), 7.45–7.44 (m, 2H), 7.29–7.19 (m, 2H),
δ
7.09 (s, 1H), 2.37 (s, 3H); 13C-NMR (100 MHz, CDCl3)
δ 141.9, 136.0, 135.6, 130.3, 128.4, 124.8, 124.7,
123.4, 123.2, 122.4, 120.7, 119.6, 114.5, 110.2, 9.6; HRMS (ESI): m/z Calcd. For: C15H11BrClN [M + H]+:
319.9836; found 319.9834.
N-(2-Fluoro-3-propylphenyl)-3-methylindole (3ao): White waxy oil (216.5 mg, 81%); 1H-NMR (400 MHz,
CDCl3)
δ
7.65 (d, J = 7.4 Hz, 1H), 7.34–7.30 (m, 2H), 7.24–7.15 (m, 4H), 7.10 (s, 1H), 2.74 (t, J = 7.6 Hz,
155.2 (d, JC-F
2H), 2.42 (s, 3H), 1.77–1.68 (m, 2H), 1.03 (t, J = 7.3 Hz, 3H); 13C-NMR (100 MHz, CDCl3)
δ
= 248.0 Hz), 136.8, 131.4 (d, JC-F = 15.0 Hz), 129.4, 128.9 (d, JC-F = 5.0 Hz), 127.4 (d, JC-F = 13.0 Hz), 126.3
(d, JC-F = 2.0 Hz), 125.2 (d, JC-F = 1.0 Hz), 124.1 (d, JC-F = 5.0 Hz), 122.4, 119.8, 119.2, 112.8, 110.7, 31.3,
23.5, 13.9, 9.7; HRMS (ESI): m/z Calcd. For: C18H18FN2 [M + H]+: 268.1496; found 268.1492.
N-(3-Fluorophenyl)-3-methylindole (3ap): White waxy oil (164.7 mg, 73%); 1H-NMR (400 MHz, CDCl3)
δ
7.66–7.60 (m, 2H), 7.49–7.43 (m, 1H), 7.31–7.20 (m, 4H), 7.14 (s, 1H), 7.05–7.01 (m, 1H), 2.41 (s, 3H);
13C-NMR (100 MHz, CDCl3)
δ
164.4 (d, JC-F = 246.0 Hz), 141.6 (d, JC-F = 10.0 Hz), 135.8, 130.9 (d,
J
C-F = 10.0 Hz), 130.1, 125.2, 122.8, 120.3, 119.4 (d, JC-F = 13.0 Hz), 113.7, 112.7 (d, JC-F = 21.0 Hz), 111.2,
111.0, 110.4, 9.7; HRMS (ESI): m/z Calcd. For: C15H12FN [M + H]+: 226.1027; found 226.1025.
2-Fluoro-6-(3-methylindol-1-yl)benzamide (3aq): White solid (203.9 mg, 76%); mp 205~208 ◦C; 1H-NMR
(400 MHz, CDCl3)
7.09 (s, 1H), 5.43 (d, J = 63.2 Hz, 2H), 2.35 (s, 3H); 13C-NMR (100 MHz, CDCl3)
C-F = 251.0 Hz), 138.3, 136.9, 131.5 (d, JC-F = 10.0 Hz), 129.6, 126.3, 123.2, 122.8, 120.3, 119.4, 115.0, 114.8,
113.7, 110.1, 9.7; HRMS (ESI): m/z Calcd. For: C16H13FN2O [M + H]+: 269.1085; found 269.1082.
δ
7.61 (d, J = 6.7 Hz, 1H), 7.55–7.47 (m, 1H), 7.34–7.24 (m, 2H), 7.23–7.15 (m, 3H),
δ
164.8, 160.2 (d,
J
N-(2-Chlorophenyl)indole (3ba) [49]: White waxy oil (111.5 mg, 49%); 1H-NMR (400 MHz, CDCl3)
(d, J = 6.5 Hz, 1H), 7.61–7.58 (m, 1H), 7.47–7.39 (m, 3H), 7.26–7.13 (m, 4H), 6.71 (d, J = 3.3 Hz, 1H);
δ 7.70
13C-NMR (100 MHz, CDCl3)
δ 137.0, 136.8, 131.9, 130.9, 129.5, 129.1, 128.8, 128.6, 127.7, 122.4, 121.1,
120.4, 110.7, 103.3; GC-MS m/z: 227 (M+).
N-Phenylindole (3bb) [50]: White solid (from 2j, 98.5 mg, 51%); 1H-NMR (400 MHz, CDCl3)
δ 7.70 (d,
J = 8.3 Hz, 1H), 7.58 (d, J = 8.2 Hz, 1H), 7.53–7.51 (m, 4H), 7.39–7.33 (m, 2H), 7.25–7.15 (m, 2H), 6.70 (d,
J = 3.3 Hz,1H); 13C-NMR (100 MHz, CDCl3)
120.4, 110.6, 103.6; GC-MS m/z: 193 (M+).
δ 139.9, 135.9, 129.7, 129.4, 128.0, 126.5, 124.5, 122.4, 121.2,