10.1002/adsc.201801367
Advanced Synthesis & Catalysis
1
mg); H NMR (600 MHz, CDCl3) δ 7.79 (dd, J = 6.3, 2.9
J = 7.5 Hz, 1H), 7.31 (d, J = 7.2 Hz, 1H), 7.30 – 7.27 (m,
Hz, 1H), 7.74 (dd, J = 6.3, 2.9 Hz, 1H), 7.70 (d, J = 8.0 Hz,
2H), 7.63 (d, J = 8.0 Hz, 2H), 7.33 – 7.28 (m, 2H), 1.63 (s,
9H). 13C NMR (151 MHz, CDCl3) δ 151.8, 143.2, 139.6,
134.9, 131.2 (q, J = 34.2 Hz), 130.2, 124.8 (q, J = 3.8 Hz),
123.0, 122.5, 122.2, 120.3, 114.7, 59.1, 31.8. HRMS (ESI-
TOF) m/z: calculated for C18H17F3N2Na+: 341.1236 (M +
Na)+, found: 341.1242.
2H), 7.25 – 7.21 (m, 2H), 2.18 (s, 3H), 1.59 (s, 9H). 13
C
NMR (151 MHz, CDCl3) δ 152.5, 143.6, 137.2, 135.6,
134.4, 129.9, 129.7, 129.1, 125.1, 121.8, 121.6, 120.1,
114.5, 58.7, 30.7, 19.9. HRMS (ESI-TOF) m/z: calculated
for C18H20N2Na+: 287.1519 (M + Na)+, found: 287.1509.
1-(tert-Butyl)-2-(2-fluorophenyl)-1H-benzo[d]imidazole
(3w): White solid; Yield: 93% (24.9 mg); 1H NMR (600
MHz, CDCl3) δ 7.83 – 7.77 (m, 1H), 7.76 – 7.72 (m, 1H),
7.49 (td, J = 7.4, 1.4 Hz, 1H), 7.47 – 7.43 (m, 1H), 7.31 –
7.27 (m, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.13 (t, J = 8.9 Hz,
Methyl
4-(1-(tert-butyl)-1H-benzo[d]imidazol-2-
1
yl)benzoate (3q): White solid; Yield: 93% (28.6 mg); H
NMR (600 MHz, CDCl3) δ 8.11 (d, J = 8.2 Hz, 2H), 7.81 –
7.76 (m, 1H), 7.76 – 7.71 (m, 1H), 7.58 (d, J = 8.2 Hz, 2H), 1H), 1.65 (s, 9H). 13C NMR (151 MHz, CDCl3) δ 160.4 (d,
7.31 – 7.27 (m, 2H), 3.96 (s, 3H), 1.62 (s, 9H). 13C NMR
(151 MHz, CDCl3) δ 166.6, 152.3, 143.3, 140.5, 134.9,
130.6, 129.8, 129.0, 122.3, 122.1, 120.3, 114.7, 59.0, 52.3,
J = 247.1 Hz), 147.3, 143.6, 134.8, 131.5 (d, J = 2.4 Hz),
131.3 (d, J = 8.0 Hz), 124.2 (d, J = 16.2 Hz), 123.9 (d, J =
3.5 Hz), 122.2, 121.8, 120.3, 115.4 (d, J = 20.2 Hz), 114.6,
58.9, 30.5. HRMS (ESI-TOF) m/z: calculated for
C17H17FN2Na+: 291.1268 (M + Na)+, found: 291.1275.
31.5.
HRMS
(ESI-TOF)
m/z:
calculated
for
C19H20N2NaO2 : 331.1417 (M + Na)+, found: 331.1428.
+
4-(1-(tert-Butyl)-1H-benzo[d]imidazol-2-yl)benzonitrile
(3r): Wite solid; Yield: 91% (25.0 mg,); H NMR (600
1-(tert-Butyl)-2-(3,4-dimethylphenyl)-1H-
1
benzo[d]imidazole (3x): White solid; Yield: 94% (26.1
mg); 1H NMR (600 MHz, CDCl3) δ 7.79 – 7.74 (m, 1H),
7.73 – 7.69 (m, 1H), 7.28 – 7.23 (m, 3H), 7.17 (q, J = 8.6
Hz, 2H), 2.32 (s, 3H), 2.30 (s, 3H), 1.63 (s, 9H). 13C NMR
(151 MHz, CDCl3) δ 153.9, 143.2, 137.4, 136.0, 134.9,
133.1, 130.6, 128.8, 127.1, 121.74, 121.67, 120.1, 114.6,
58.8, 31.4, 19.69, 19.67. HRMS (ESI-TOF) m/z: calculated
for C19H22N2Na+: 301.1675 (M + Na)+, found: 301.1678.
MHz, CDCl3) δ 7.80 – 7.76 (m, 1H), 7.74 (d, J = 8.3 Hz,
3H), 7.63 (d, J = 8.2 Hz, 2H), 7.34 – 7.28 (m, 2H), 1.63 (s,
9H). 13C NMR (151 MHz, CDCl3) δ 151.2, 143.3, 140.7,
134.9, 131.6, 130.5, 122.7, 122.3, 120.4, 118.3, 114.8,
113.0, 59.1, 31.6. HRMS (ESI-TOF) m/z: calculated for
C18H17N3Na+: 298.1315 (M + Na)+, found: 298.1322.
1-(tert-Butyl)-2-(m-tolyl)-1H-benzo[d]imidazole
(3s):
White solid; Yield: 96% (25.4 mg); 1H NMR (600 MHz,
CDCl3) δ 7.79 – 7.76 (m, 1H), 7.74 – 7.70 (m, 1H), 7.33 –
7.25 (m, 6H), 2.40 (s, 3H), 1.63 (s, 9H). 13C NMR (151
MHz, CDCl3) δ 153.8, 143.3, 137.5, 135.7, 134.8, 130.2,
129.6, 127.5, 126.8, 121.8, 121.7, 120.1, 114.6, 58.8, 31.4,
21.3. HRMS (ESI-TOF) m/z: calculated for C18H20N2Na+:
287.1519 (M + Na)+, found: 287.1511.
1-(tert-Butyl)-2-(naphthalen-2-yl)-1H-
benzo[d]imidazole (3y): White solid; Yield: 96% (28.8
mg); 1H NMR (600 MHz, CDCl3) δ 8.01 (s, 1H), 7.92 –
7.87 (m, 3H), 7.84 – 7.80 (m, 1H), 7.78 – 7.74 (m, 1H),
7.59 – 7.52 (m, 3H), 7.33 – 7.28 (m, 2H), 1.65 (s, 9H). 13C
NMR (151 MHz, CDCl3) δ 153.5, 143.4, 135.0, 133.2,
132.5, 129.1, 128.2, 127.8, 127.3, 127.2, 126.8, 126.6,
122.0, 121.9, 120.2, 114.7, 58.9, 31.5. HRMS (ESI-TOF)
m/z: calculated for C21H20N2Na+: 323.1519 (M + Na)+,
found: 323.1528.
1-(tert-Butyl)-2-(3-methoxyphenyl)-1H-
benzo[d]imidazole (3t): White solid; Yield: 81% (22.7
1
mg); H NMR (600 MHz, CDCl3) δ 7.80 – 7.77 (m, 1H),
7.74 – 7.71 (m, 1H), 7.32 (t, J = 7.9 Hz, 1H), 7.29 – 7.25
(m, 2H), 7.06 (d, J = 7.5 Hz, 1H), 7.04 (s, 1H), 7.00 (dd, J
= 8.3, 2.0 Hz, 1H), 3.84 (s, 3H), 1.64 (s, 9H). 13C NMR
(151 MHz, CDCl3) δ 158.9, 153.3, 143.2, 137.0, 134.8,
1-(tert-Butyl)-2-(furan-2-yl)-1H-benzo[d]imidazole (3z):
White solid; Yield: 94% (22.6 mg); H NMR (600 MHz,
CDCl3) δ 7.83 – 7.78 (m, 1H), 7.77 – 7.71 (m, 1H), 7.55 (s,
1
128.8, 122.4, 122.0, 121.8, 120.2, 115.1, 114.9, 114.6, 58.9, 1H), 7.30 – 7.27 (m, 2H), 6.76 (d, J = 3.1 Hz, 1H), 6.55 –
55.3, 31.3. HRMS (ESI-TOF) m/z: calculated for
6.53 (m, 1H), 1.68 (s, 9H). 13C NMR (151 MHz, CDCl3) δ
146.0, 143.6, 143.0, 142.5, 135.1, 122.8, 122.0, 120.7,
114.6, 112.6, 111.4, 59.2, 30.2. HRMS (ESI-TOF) m/z:
calculated for C15H16N2NaO+: 263.1155 (M + Na)+, found:
263.1159.
C18H20N2NaO+:303.1468 (M + Na)+, found: 303.1462.
1-(tert-Butyl)-2-(3-fluorophenyl)-1H-benzo[d]imidazole
(3u): White solid; Yield: 94% (25.1 mg); 1H NMR (600
MHz, CDCl3) δ 7.80 – 7.77 (m, 1H), 7.74 – 7.71 (m, 1H),
7.40 (dd, J = 13.8, 7.8 Hz, 1H), 7.32 – 7.27 (m, 3H), 7.22
(d, J = 8.9 Hz, 1H), 7.17 (td, J = 8.5, 1.9 Hz, 1H), 1.64 (s,
9H). 13C NMR (151 MHz, CDCl3) δ 161.9 (d, J = 248.3
Hz), 151.9 (d, J = 2.4 Hz), 143.2, 137.8 (d, J = 8.1 Hz),
134.8, 129.4 (d, J = 8.3 Hz), 125.7 (d, J = 3.1 Hz), 122.3,
122.0, 120.3, 117.0 (d, J = 22.1 Hz), 116.1 (d, J = 20. 6
Hz), 114.7, 59.0, 31.4. HRMS (ESI-TOF) m/z: calculated
for C17H17FN2Na+: 291.1268 (M + Na)+, found: 291.1265.
1-(tert-Butyl)-2-(thiophen-2-yl)-1H-benzo[d]imidazole
1
(3aa): White solid; Yield: 93% (23.8 mg); H NMR (600
MHz, CDCl3) δ 7.82 – 7.76 (m, 1H), 7.76 – 7.70 (m, 1H),
7.47 (dd, J = 5.1, 0.9 Hz, 1H), 7.29 – 7.27 (m, 2H), 7.25
(dd, J = 3.5, 0.9 Hz, 1H), 7.08 (dd, J = 5.1, 3.5 Hz, 1H),
1.70 (s, 9H). 13C NMR (151 MHz, CDCl3) δ 146.5, 143.1,
135.2, 135.1, 130.3, 127.3, 126.3, 122.4, 122.0, 120.4,
114.7, 59.4, 31.0. HRMS (ESI-TOF) m/z: calculated for
C15H16N2NaS+: 279.0926 (M + Na)+, found: 279.0936.
1-(tert-Butyl)-2-(o-tolyl)-1H-benzo[d]imidazole
(3v):
White solid; Yield: 98% (25.8 mg); 1H NMR (600 MHz,
1-(tert-Butyl)-2-(pyridin-4-yl)-1H-benzo[d]imidazole
1
CDCl3) δ 7.81 – 7.77 (m, 1H), 7.76 – 7.71 (m, 1H), 7.34 (t,
(3ab): White solid; Yield: 71% (17.8 mg); H NMR (600
6
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