Molecules 2012, 17
12514
1
5
1
1
-Bromo-2-phenyl-1H-benzo[d]imidazole (2d). White solid; m.p. 202–203 °C; yield: 54%. H-NMR: δ
1
3
3.09 (br s, 0.26H), 8.18–8.16 (d, 2H, J = 8.0 Hz), 7.87–7.50 (m, 5H), 7.37–7.33 (m, 1H). C-NMR: δ
45.20, 142.82, 130.27, 129.54, 129.01, 126.57, 125.21, 124.70, 114.71, 113.87, 113.07. HRMS-ESI
+
(
m/z): [M+Na] calcd. for C H BrN Na 294.9847; found 294.9849.
1
3
9
2
1
5
1
1
-Methyl-2-phenyl-1H-benzo[d]imidazole (2e). White solid; m.p. 242–243 °C; yield: 67%. H-NMR: δ
13
2.80 (br s, 0.22H), 8.20 (m, 2H), 7.55 (m, 5H), 7.05 (m, 1H), 2.45 (s, 3H). C-NMR: δ 150.80,
41.94, 135.08, 131.53, 130.24, 129.59, 128.84, 128.01, 126.26, 123.51, 118.29, 110.86, 21.27.
+
HRMS-ESI (m/z): [M+Na] calcd. for C H N Na 231.0898; found 231.0896.
1
4
12
2
1
5
-Methoxy-2-phenyl-1H-benzo[d]imidazole (2f). White solid; m.p. 148–150 °C; yield: 67%. H-NMR:
δ 13.07 (br s, 0.13H), 8.29–8.13 (m, 2H), 7.58–7.48 (m, 4H), 7.25–7.08 (m, 1H), 7.02–7.01 (m, 1H),
1
3
3
.83–3.82 (s, 3H). C-NMR: δ 156.8, 151.4, 137.4, 136.2, 130.4 (130.1), 129.4 (129.2), 127.5, 126.8,
+
1
14.2, 112.4, 94.99 (94.94), 56.4. HRMS-ESI (m/z): [M+Na] calcd. for C H N NaO 247.0847;
1
4
12
2
found 247.0849.
1
2
-Phenyl-3H-imidazo[4,5-b]pyridine (2g). White solid; m.p. 283–284 °C; yield: 44%. H-NMR δ
1
3.48 (br s, 1H), 8.34 (dd, J = 4.8, 1.5 Hz, 1H), 8.25−8.21 (m, 2H), 8.02 (d, J = 7.5 Hz, 1H), 7.61−7.51
1
3
(
m, 3H), 7.25 (dd, J = 8.1, 4.8 Hz, 1H). C-NMR: δ 152.32, 143.75, 135.57, 130.52, 129.57, 129.00,
+
1
2
26.70, 126.27, 119.16, 118.09. HRMS-ESI (m/z): [M+Na] calcd. for C12
H
9
N
3
Na 218.0694; found
18.0697.
1
2
-p-Tolyl-1H-benzo[d]imidazole (2i). White solid; m.p. 276–278 °C; yield: 60%. H-NMR: δ 12.83
(
br s, 0.15H), 8.09–8.07 (d, 2H, J = 7.6 Hz), 7.65–7.53 (m, 2H), 7.37–7.35 (d, 2H, J = 8.0 Hz), 7.20
1
3
(
m, 2H), 2.39 (s, 3H). C-NMR: δ 151.17, 143.71, 139.49, 134.74, 129.42, 127.31, 126.30, 122.23,
+
1
2
21.50, 118.62, 111.04, 20.87. HRMS-ESI (m/z): [M+Na] calcd. for C14
H
12
N
2
Na 231.0898; found
31.0895.
1
2
-(4-Methoxyphenyl)-1H-benzo[d]imidazole (2j). White solid; m.p. 221–223 °C; yield: 63%. H-NMR:
δ 12.76 (br s, 0.11H), 8.14–8.12 (d, 2H, J = 8.8 Hz), 7.57 (m, 2H), 7.20–7.17 (m, 2H), 7.13–1.11 (d,
1
3
2
H, J = 8.8 Hz), 3.85 (s, 3H). C-NMR: δ 160.59, 151.25, 143.73, 134.97, 127.98, 122.61, 122.07,
+
1
21.74, 118.43, 114.34, 111.05, 55.29. HRMS-ESI (m/z): [M+Na] calcd. for C H N NaO 247.0847;
1
4
12
2
found 247.0851.
1
2
-o-Tolyl-1H-benzo[d]imidazole (2k). White solid; m.p. 206–208 °C; yield: 58%. H-NMR δ 12.64 (br
s, 0.11H), 7.76–7.74 (d, 1H, J = 6.8 Hz), 7.62 (m, 2H), 7.39–7.37 (m, 3H), 7.23–7.21 (m, 2H), 2.62 (s,
1
3
3
H). C-NMR δ 151.73, 136.91, 131.15, 129.94, 129.33, 129.22, 125.85, 121.78, 20.90. HRMS-ESI
+
(
m/z): [M+Na] calcd. for C14
H
12
N
2
Na 231.0898; found 231.0901.
1
2
-(2-Methoxyphenyl)-1H-benzo[d]imidazole (2l). White solid; m.p. 181–182 °C; yield: 64%. H-NMR
δ 12.13 (br s, 0.22H), 8.35–8.32 (dd, 1H, J = 7.6, 1.6 Hz), 7.66–7.62 (m, 2H), 7.52–7.47 (m, 1H),
1
3
7
1
5
.27–7.25 (d, 1H, J = 8.0 Hz), 7.21–7.19 (m, 2H), 7.15–7.11 (m, 1H), 4.04 (s, 3H). C-NMR δ 156.74,
52.87, 141.72, 141.68, 131.25, 129.70, 122.02, 129.33, 121.50, 120.85, 118.45, 117.93, 112.07,
+
5.74. HRMS-ESI (m/z): [M+Na] calcd. for C14
H
12
N
2
NaO 247.0847; found 247.0849.