The Journal of Organic Chemistry
Page 12 of 22
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121.7, 119.8, 118.9, 117.8, 109.2, 48.1, 32.7 ppm. HRMS (ESI-TOF) m/z: [M + H]+ Calcd for
C22H19ClN 332.1201; Found 332.1209.
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3-benzhydryl-5-bromo-1-methyl-1H-indole(3o);
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2-benzhydryl-5-bromo-1-methyl-1H-indole(3o’). 18 h, white solid, 45.8 mg, mp 113-115 °C , 61%
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yield; 3o:3o’ =2.5:1; H NMR (500 MHz, CDCl3) δ7.25-7.15 (m, 10H), 7.14-7.07-7.03 (m, 3H),
6.34 (s, 1H), 5.52 (s, 1H), 3.59 (s, 3H) ppm. 13C{1H} NMR (126 MHz, CDCl3) δ 142.9, 142.6,
140.4, 135.4, 135.0, 128.8, 128.0, 127.8, 127.5, 127.3, 125.9, 125.3, 123.5, 122.9, 121.6, 121.3,
116.9, 111.5, 111.3, 109.6, 109.2, 101.5, 88.9, 59.3, 48.8, 47.4, 31.8 ppm. HRMS (ESI-TOF) m/z:
[M + H]+ Calcd for C22H19BrN 376.0701; Found 376.0704.
3,4,6-tribenzhydryl-1-methyl-2-phenyl-1H-indole (3p). 18 h, white solid, 98.7 mg, mp
173-176 °C , 70 yield; 1H NMR (500 MHz, CDCl3) δ 7.35-7.33 (m, 3H), 7.19-7.16 (m, 6H), 7.12
(d, J = 7 Hz, 2H), 7.08-7.06 (m, 6H), 7.01-7.00 (m, 6H), 6.90 (d, J = 7.5 Hz, 4H), 6.84-6.83 (m,
4H), 6.67-6.56 (d, J = 7.5 Hz, 4H), 6.62 (s, 2H), 5.61 (s, 1H), 5.47 (s, 1H), 5.26 (s, 1H), 3.27 (s,
3H) ppm. 13C{1H} NMR (126 MHz, CDCl3) δ 144.3, 144.2, 138.7, 136.4, 136.1, 134.5, 131.9,
130.7, 129.7, 129.4, 128.9, 128.3, 128.2, 128.1, 128.0, 127.9, 126.2, 125.9, 125.6, 124.8, 124.3,
115.6, 110.9, 53.0, 52.4, 48.2, 30.8 ppm. HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C54H43NNa
728.3293; Found 728.3294.
2,3,6-tribenzhydryl-5-methoxy-1-methyl-1H-indole (3q). 18 h, white solid, 108.1 mg, mp
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210-213 °C, 82% yield; H NMR (500 MHz, CDCl3) δ 7.23-7.22 (m, 4H), 7.20-7.16 (m, 10H),
7.15-7.11 (m, 8H), 7.08-7.06 (d, J = 7.5 Hz, 4H), 6.99-6.97 (d, J = 7 Hz, 4H), 6.59 (s, 1H), 6.19 (s,
1H), 5.98 (s, 1H), 5.91 (s, 1H), 5.46 (s, 1H), 3.26 (s, 3H), 3.13 (s, 3H) ppm. 13C{1H} NMR (126
MHz, CDCl3) δ 151.5, 144.6, 144.1, 140.9, 137.5, 132.1, 129.5, 129.2, 128.3, 128.0, 127.9, 127.6,
126.5, 126.1, 125.9, 125.8, 115.0, 110.2, 102.1, 55.9, 50.4, 47.7, 47.6, 31.3 ppm. HRMS
(ESI-TOF) m/z: [M + H]+ Calcd for C49H42NO 660.3266; Found 660.3262.
2,3,6-tribenzhydryl-5-methoxy-1-methyl-1H-indole (3r). 18 h, white solid, 86.2 mg, mp
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216-218 °C , 65% yield; H NMR (500 MHz, CDCl3) δ 7.18-7.15 (m, 4H), 7.14-7.05 (m, 14H),
7.03 (d, J = 6 Hz, 4H), 6.96 (d, J = 3 Hz, 4H), 6.90 (d, J = 5 Hz, 4H), 6.77 (d, J = 4.5 Hz, 1H),
6.59 (d, J = 4.5 Hz, 1H), 5.91 (d, J = 4.5 Hz, 2H), 5.40 (s, 1H), 3.04 (s, 3H) ppm. 13C{1H} NMR
(126 MHz, CDCl3) δ 143.6, 143.5, 140.5, 139.0, 136.0, 134.2, 129.7, 129.3, 129.2, 128.5, 128.3,
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