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The Journal of Organic Chemistry
128.7, 128.6, 128.1, 128.0, 127.7, 126.2, 124.6, 121.9, 119.3, 119.1, 110.5, 29.6, 21.1. 31P NMR (162 MHz, CDCl3) δ 21.58.
HRMS (ESI) calcd. for C30H25NOP+ (M+H+) 446.1668, found: 446.1665.
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1-(4-(2-(diphenylphosphoryl)-9H-pyrrolo[1,2-a]indol-1-yl)phenyl)ethan-1-one (3m): m.p.: 263.8ꢀ267.6 °C, light
yellow solid (21.1 mg, 45%). 1H NMR (400 MHz, CDCl3) δ 7.79 – 7.72 (m, 8H), 7.48 – 7.43 (m, 3H), 7.39ꢀ7.34 (m, 4H),
7.31 (d, J = 7.3 Hz, 1H), 7.25 – 7.18 (m, 2H), 6.91 (d, J = 4.1 Hz, 1H), 4.06 (s, 2H), 2.51 (s, 3H). 13C NMR (100 MHz,
CDCl3) δ 197.9, 139.4, 139.3, 136.6, 136.5, 134.5, 134.2, 133.3 (d, J = 107.7 Hz), 132.6, 131.9, 131.8, 131.6, 131.6, 131.3,
130.8, 130.7, 129.0, 128.9, 128.5, 128.3, 128.2, 127.9, 126.3, 125.0, 120.9, 120.9, 120.2, 119.9, 118.0, 116.8, 110.7, 30.0,
26.6. 31P NMR (162 MHz, CDCl3) δ 21.61. HRMS (ESI) calcd. for C31H25NO2P+ (M+H+) 474.1617, found: 474.1622.
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(1-(4-fluorophenyl)-9H-pyrrolo[1,2-a]indol-2-yl)diphenylphosphine oxide (3n): m.p.: 265.5ꢀ267.9 °C, light yellow
solid (22.7 mg, 51%). 1H NMR (400 MHz, CDCl3) δ 7.79ꢀ7.69 (m, 4H), 7.62 – 7.55 (m, 2H), 7.48ꢀ7.41 (m, 3H), 7.38 –
7.33 (m, 4H), 7.30 (d, J = 7.1 Hz, 1H), 7.23 (d, J = 7.6 Hz, 1H), 7.20ꢀ7.16 (m, 1H), 6.93 (d, J = 4.0 Hz, 1H), 6.84 (t, J = 8.8
Hz, 2H), 3.99 (s, 2H).13C NMR (100 MHz, CDCl3) δ161.3 (d, J = 243.7 Hz), 139.7, 135.3, 135.2, 134.4, 133.6 (d, J = 107.2
Hz), 131.9, 131.8, 131.4, 131.4, 130.4, 130.3, 128.2, 128.1, 127.8, 126.2, 124.7, 121.0, 120.9, 119.3, 119.1, 118.1, 116.9,
115.0, 114.7, 110.6, 29.4. 19F NMR (376 MHz, CDCl3) δ ꢀ116.40. 31P NMR (162 MHz, CDCl3) δ 21.15. HRMS (ESI) calcd.
for C29H22FNOP+ (M+H+) 450.1418, found: 450.1416.
(1-(4-(tert-butyl)phenyl)-9H-pyrrolo[1,2-a]indol-2-yl)di-p-tolylphosphine oxide (3o) : m.p.: 105.5ꢀ106.8 °C, light
yellow solid (24.0 mg, 47%). 1H NMR (400 MHz, CDCl3) δ 7.64ꢀ7.58 (m, 4H), 7.46 (d, J = 8.3 Hz, 2H), 7.42 (d, J = 7.5
Hz, 1H), 7.31 – 7.27 (m, 1H), 7.22 (d, J = 7.6 Hz, 1H), 7.17 – 7.10 (m, 7H), 6.97 (d, J = 4.0 Hz, 1H), 4.01 (s, 2H), 2.32 (s,
6H), 1.23 (s, 9H). 13C NMR (100 MHz, CDCl3) δ 148.7, 141.3, 141.3, 139.8, 134.9, 134.8, 134.6, 131.9, 131.8, 131.5,
131.4, 130.9 (d, J = 109.6 Hz), 128.8, 128.7, 128.4, 127.7, 126.2, 124.7, 124.5, 121.8, 121.7, 119.2, 119.0, 118.6, 117.4,
110.5, 34.3, 31.3, 29.5, 21.5. 31P NMR (162 MHz, CDCl3) δ 21.49. HRMS (ESI) calcd. for C35H35NOP+ (M+H+) 516.2451,
found: 516.2454.
di-p-tolyl(1-(p-tolyl)-9H-pyrrolo[1,2-a]indol-2-yl)phosphine oxide (3p): m.p.: 94.3ꢀ96.0 °C, light yellow solid (23.0
mg, 49%). 1H NMR (400 MHz, CDCl3) δ 7.64ꢀ7.57 (m, 4H), 7.50 (d, J = 8.1 Hz, 2H), 7.43 (d, J = 7.4 Hz, 1H), 7.29 (t, J =
7.7 Hz, 1H), 7.22 (d, J = 7.6 Hz, 1H), 7.18 – 7.13 (m, 5H), 6.97 (d, J = 8.0 Hz, 2H), 6.92 (d, J = 4.0 Hz, 1H), 4.00 (s, 2H),
2.35 (s, 6H), 2.24 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 141.5, 139.8, 135.5, 135.2, 135.1, 134.6, 131.9, 131.8, 131.5,
130.9 (d, J = 109.7 Hz), 128.9, 128.8, 128.7, 128.6, 127.6, 126.2, 124.5, 119.3, 119.1, 110.5, 29.6, 21.6, 21.1. 31P NMR (162
MHz, CDCl3) δ 21.68. HRMS (ESI) calcd. for C32H28NNaOP+ (M+Na+
) 496.1801, found: 496.1805.
diphenyl(1-(m-tolyl)-9H-pyrrolo[1,2-a]indol-2-yl)phosphine oxide (3q): m.p.: 71.6ꢀ72.8 °C, light yellow solid (22.7
mg, 42%). 1H NMR (400 MHz, CDCl3) δ 7.64ꢀ7.57 (m, 4H), 7.42 (d, J = 8.3 Hz, 2H), 7.13 (t, J = 8.7 Hz, 7H), 7.00 (s, 1H),
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