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7.38 (d, J ¼ 7.2 Hz, 2H), 7.32 (t, J ¼ 7.6 Hz, 2H), 7.23 (t, J ¼ 7.2 Hz, 1H),
7.09–7.16 (m, 2H), 5.09–5.16 (m, 1H), 3.78 (d, J ¼ 12.0 Hz, 1H), 3.60
(d, J ¼ 12.0 Hz, 1H), 3.11 (t, J ¼ 8.4 Hz, 1H), 2.96 (dd, J ¼ 10.4, 3.6 Hz,
1H), 2.70 (t, J ¼ 10.0 Hz, 1H), 2.54 (s, 3H), 2.33–2.45 (m, 2H), 2.01–2.11
(m, 1H). 13C NMR (DMSO-d6): d 151.7, 142.9, 138.8, 132.7, 128.5, 128.2,
127.0, 121.1, 121.1, 118.4, 111.8, 59.2, 57.2, 53.6, 53.4, 30.3, 14.1. Mp:
93.8–94.58C. Anal. calc. for C19H21N3: C, 78.32; H, 7.26; N, 14.42. Found:
C, 78.02; H, 7.46; N, 14.55. HRMS: Calc. for C19H22N3: 292.1814. Found
292.1821.
2-Methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-benzimidazole (3c): 1H NMR
(DMSO-d6): d 7.71 (d, J ¼ 8.8 Hz, 1H), 7.51 (d, J ¼ 8.8 Hz, 1H), 7.09–
7.15 (m, 2H), 4.52–4.61 (m, 1H), 4.02 (dd, J ¼ 11.6, 4.4 Hz, 2H), 3.54
(t, J ¼ 11.6 Hz, 2H), 2.58 (s, 3H), 2.37 (qd, J ¼ 12.4, 4.4 Hz, 2H), 1.79
(dd, J ¼ 12.4, 2.4 Hz, 2H). 13C NMR (DMSO-d6): d 151.4, 142.8, 133.5,
121.3, 120.9, 118.6, 111.5, 66.6, 52.3, 30.7, 14.6. Mp: 167–1718C. Anal.
calc. for C13H16N2O: C, 72.19; H, 7.46; N, 12.95. Found: C, 72.30; H,
7.43; N, 12.97. HRMS: calc. for C13H17N2O: 217.1341. Found 217.1339.
2-Methyl-1-(tetrahydro-2H-thiopyran-4-yl)-1H-benzimidazole (4c): 1H
NMR (DMSO-d6): d 8.00–8.03 (m, 1H), 7.78–7.80 (m, 1H), 7.52–7.55
(m, 2H), 4.67 (m, 1H), 2.99 (t, J ¼ 12.0 Hz, 2H), 2.87 (s, 3H), 2.79
(d, J ¼ 12.0 Hz, 2H), 2.43 (qd, J ¼ 12.8, 3.2 Hz, 2H), 2.31 (dd, J ¼ 12.8,
3.2 Hz, 2H). 13C NMR (DMSO-d6): d 151.1, 130.5, 130.1, 125.5, 125.3,
114.2, 114.2, 56.2, 31.5, 27.5, 12.5. Mp: 2708C dec. Anal. calc. for
C13H17ClN2S: C, 58.09; H, 6.37; N, 10.42. Found: C, 58.09; H, 6.42; N,
10.39. HRMS: calc. for C13H17N2S: 233.1112. Found 233.1106.
2-Methyl-1-(1,2,3,4-tetrahydro-2-naphthalenyl)-1H-benzimidazole (7c): 1H
NMR (CD2Cl2): 7.64 (d, J ¼ 8.4 Hz, 1H), 7.48 (d, J ¼ 6.8 Hz, 1H), 7.21–
7.14 (m, 6H), 4.75–4.66 (m, 1H), 3.65 (dd, 1H, J ¼ 16.4, 11.6 Hz), 3.10
(m, 3H), 2.77–2.66 (m, 1H), 2.63 (s, 3H), 2.26–2.23 (m, 1H). 13C NMR
(CD2Cl2): 152.0, 144.0, 136.0, 135.0, 134.4, 129.7, 129.3, 126.9, 126.6,
122.0, 121.8, 119.7, 111.7, 53.8, 34.3, 30.2, 28.7, 15.4. HRMS: calc. for
C18H19N2: 263.1548. Found 263.1545.
2-Methyl-1-(1-phenylethyl)-1H-benzimidazole (8c): 1H NMR (CD2Cl2): 7.62
(d,1H, J ¼ 10.0 Hz),7.33(m, 3H),7.23(m, 2H),7.14(m, 1H),7.04(m, 2H),5.78
(q, 1H, J ¼ 9.0 Hz), 2.58 (s, 3H), 1.97 (d, 3H, J ¼ 9.0 Hz). 13C NMR (CD2Cl2):
152.2, 143.8, 140.4, 134.6, 129.2, 128.2, 126.9, 122.0, 121.8, 119.5, 111.6, 53.9,
18.8, 15.3. HRMS: calc. for C16H17N2: 237.1392. Found 237.1394.
2-Methyl-1-[(2E)-1-methyl-3-phenyl-2-propen-1-yl]-1H-benzimidazole (9c):
1H NMR (CD2Cl2): 7.65 (m, 1H), 7.47 (m, 1H), 7.40–7.38 (m, 2H), 7.35–
7.27 (m, 3H), 7.19 (m, 2H), 6.55 (s, 2H), 5.31 (q, 1H), 2.65 (s, 3H), 1.80
(d, J ¼ 8.5 Hz, 3H). 13C NMR (CD2Cl2): 151.8, 143.7, 136.7, 134.5, 131.8,
129.2, 129.1, 128.5, 126.9, 122.1, 121.9, 119.4, 111.8, 53.0, 19.2, 15.2.