Page 15 of 21
The Journal of Organic Chemistry
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(
s, 1H), 0.93 (s, 9H). C{ H} NMR (101 MHz, CDCl
34.6, 133.1, 132.5, 129.2, 128.8, 128.4, 127.89, 127.88, 127.6, 127.5, 127.3, 126.2, 125.2,
122.8, 120.7, 120.6, 111.7, 102.7, 58.0, 29.5. HRMS (CI): m/z calcd for C29
[M + H]+ ,
03.2174; found, 403.2170.
3
) δ 143.79 (s), 140.6, 138.9, 135.6,
1
H
27
N
2
4
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N-tert-butyl-1-(4-(methylthio)phenyl)-1-(2-phenyl-1H-indol-1-yl)methanimine (3l): Yellow
1
solid (145 mg, 81%). Mp: 94.6-96.4 ℃. EtOAc/petroleum ether = 1/100. H NMR (400 MHz,
CDCl
3
) δ 7.66 (d, J = 6.8 Hz, 1H), 7.52 (d, J = 7.2 Hz, 2H), 7.42 (d, J = 8.0 Hz, 2H), 7.30 –
7
.23 (m, 3H), 7.15 – 7.08 (m, 4H), 6.99 (d, J = 7.2 Hz, 1H), 6.89 (s, 1H), 2.43 (s, 3H), 0.89 (s,
1
3
1
9H). C{ H} NMR (101 MHz, CDCl
3
) δ 143.3, 142.1, 140.4, 138.6, 134.6, 132.4, 128.8,
1
28.4, 127.9, 127.8, 127.4, 125.6, 122.7, 120.7, 120.6, 111.6, 102.6, 57.8, 29.5, 15.1. HRMS
+
(
CI): m/z calcd for C26
H
27
N S [M + H] , 399.1895; found, 399.1901.
2
N-tert-butyl-1-(3,4-dichlorophenyl)-1-(2-phenyl-1H-indol-1-yl)methanimine (3m): White
1
solid (87 mg, 46%). Mp: 171.4-173.2 ℃. EtOAc/petroleum ether = 1/60. H NMR (400 MHz,
CDCl
3
) δ 7.87 (s, 1H), 7.68 (d, J = 7.8 Hz, 1H), 7.47 (d, J = 7.2 Hz, 2H), 7.33 – 7.26 (m, 4H),
7
9
1
.19 – 7.12 (m, 2H), 7.03 (d, J = 8.0 Hz, 1H), 6.97 (d, J = 6.8 Hz, 1H), 6.90 (s, 1H), 0.91 (s,
1
3
1
H). C{ H} NMR (101 MHz, CDCl ) δ 141.8, 140.2, 138.4, 138.0, 135.0, 133.1, 132.1,
3
30.6, 129.9, 128.9, 128.1, 127.9, 127.4, 127.1, 123.0, 121.0, 120.8, 111.2, 103.1, 58.4, 29.3.
+
HRMS (CI): m/z calcd for C25
H
23Cl
2
N
2
[M + H] , 421.1238; found, 421.1239.
N-tert-butyl-1-(2-phenyl-1H-indol-1-yl)-1-(4-vinylphenyl)methanimine (3n): Pale yellow solid
1
(47 mg, 28%). Mp: 121.0-122.7 ℃. EtOAc/petroleum ether = 1/100. H NMR (400 MHz,
CDCl ) δ 7.67 (d, J = 7.6 Hz, 1H), 7.53 (d, J = 7.2 Hz, 2H), 7.47 (d, J = 8.0 Hz, 2H), 7.32 (d,
3
J = 8.0 Hz, 2H), 7.29 – 7.22 (m, 3H), 7.17 – 7.08 (m, 2H), 6.99 (d, J = 7.4 Hz, 1H), 6.90 (s,
1H), 6.69 (dd, J = 17.6, 11.2 Hz, 1H), 5.76 (d, J = 17.6 Hz, 1H), 5.28 (d, J = 10.8 Hz, 1H),
13
1
0
1
5
.90 (s, 9H). C{ H} NMR (101 MHz, CDCl ) δ 143.4, 140.4, 139.7, 138.6, 137.3, 136.2,
3
32.4, 128.7, 128.3, 127.84, 127.82, 127.5, 126.5, 122.7, 120.6, 120.6, 115.2, 111.6, 102.6,
+
7.9, 29.5. HRMS (CI): m/z calcd for C27
H N
27 2
[M + H] , 379.2174; found, 379.2172.
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-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butyl)-1-(2-phenyl-1H-indol-1-yl)methanimine (3o):
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White solid (155 mg, 87%). Mp: 170.6-173.4 ℃. EtOAc/petroleum ether = 1/80. H NMR
(400 MHz, CDCl
3
) δ 7.70 – 7.65 (m, 1H), 7.56 (d, J = 7.4 Hz, 2H), 7.34 – 7.25 (m, 4H), 7.17
–
1
7.11 (m, 2H), 7.07 – 6.99 (m, 1H), 6.90 (s, 1H), 6.78 (d, J = 8.4 Hz, 1H), 6.63 (d, J = 8.0 Hz,
1
3
1
H), 5.96 (s, 2H), 0.90 (s, 9H). C{ H} NMR (101 MHz, CDCl ) δ 149.9, 148.2, 143.0,
3
140.3, 138.7, 132.6, 132.4, 128.7, 127.84, 127.78, 127.4, 123.0, 122.7, 120.7, 120.6, 111.6,
[M + H]+ ,
1
3
08.2, 108.0, 102.6, 101.5, 57.7, 29.5. HRMS (CI): m/z calcd for C26
H
25
N
2
O
2
97.1916; found, 397.1906.
1-([1,1'-biphenyl]-4-yl)-N-(tert-butyl)-1-(2-phenyl-1H-indol-1-yl)methanimine (3p): Pale
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yellow solid (147 mg, 76%). Mp: 68.9-69.9 ℃. EtOAc/petroleum ether = 1/100. H NMR
(
400 MHz, CDCl
3
) δ 7.96 (s, 1H), 7.73 – 7.68 (m, 1H), 7.63 (d, J = 6.4 Hz, 1H), 7.60 (d, J =
7.6 Hz, 2H), 7.53 (d, J = 7.2 Hz, 2H), 7.42 (t, J = 7.4 Hz, 2H), 7.35 (d, J = 6.8 Hz, 3H), 7.31
(
d, J = 7.6Hz, 2H), 7.28 – 7.23 (m, 1H), 7.20 – 7.12 (m, 2H), 7.08 (d, J = 6.4 Hz, 1H), 6.94 (s,
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