Page 11 of 18
The Journal of Organic Chemistry
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136.7, 135.7, 130.5, 130.4, 127.6, 126.5, 126.2, 125.0, 113.3, 52.8; HRMS (ESI) m/z calcd for C15H13N2O4S+
([M+H]+): 317.0596, found: 317.0590.
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5-phenyl-1-(phenylsulfonyl)-1H-indazole (1j). This compound was prepared according to a
similar method to 2a and the desired product was obtained after purification by silica gel column
chromatography (Heptane/EtOAc = 6:4). Light yellow solid (153 mg, 93%); 1H NMR (400 MHz, DMSO-d6)
δ 8.63 (d, J = 0.9 Hz, 1H), 8.24 (dd, J = 8.8, 0.9 Hz, 1H), 8.13 (d, J = 1.8 Hz, 1H), 7.99 (ddd, J = 8.7, 4.0, 1.7
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Hz, 3H), 7.78 – 7.70 (m, 3H), 7.69 – 7.58 (m, 2H), 7.50 (dd, J = 8.4, 6.8 Hz, 2H), 7.45 – 7.37 (m, 1H); 13
C
{1H} NMR (101 MHz, DMSO-d6) δ 143.5, 139.8, 139.6, 137.5, 136.8, 135.5, 130.4, 129.6, 129.5, 128.1,
128.1, 127.5, 127.5, 127.1, 126.0, 120.4, 113.5; HRMS (ESI) m/z calcd for C19H15N2O2S+ ([M+H]+):
335.0854, found: 335.0850.
5-phenyl-1-(phenylsulfonyl)-1H-indole (1k). This compound was prepared according to a similar
method to 2a and the desired product was obtained after purification by silica gel column
chromatography (Heptane/EtOAc = 6:4). Light yellow solid (387 mg, 87%); 1H NMR (400 MHz, DMSO-d6)
δ 8.12 – 8.01 (m, 3H), 7.90 (t, J = 2.9 Hz, 2H), 7.73 – 7.65 (m, 4H), 7.64 – 7.57 (m, 2H), 7.46 (dd, J = 8.4,
7.0 Hz, 2H), 7.40 – 7.32 (m, 1H), 6.93 (dd, J = 3.7, 0.8 Hz, 1H); 13C {1H} NMR (101 MHz, DMSO-d6) δ 140.6,
137.6, 136.45, 135.1, 134.0, 131.7, 130.3, 129.4, 128.1, 127.7, 127.4, 127.1, 124.4, 120.2, 113.9, 110.4;
HRMS (ESI) m/z calcd for C20H16NO2S+ ([M+H]+): 334.0902, found: 334.0895.
Methyl 1-(phenylsulfonyl)-1H-indole-5-carboxylate (1l). This compound was prepared according
to a similar method to 2a and the desired product was obtained after purification by silica gel column
chromatography (Heptane/EtOAc = 6:4). Light yellow solid (418 mg, 93%); 1H NMR (400 MHz, DMSO-d6)
δ 8.30 (dd, J = 1.7, 0.7 Hz, 1H), 8.18 – 8.03 (m, 3H), 8.02 – 7.95 (m, 2H), 7.79 – 7.71 (m, 1H), 7.67 – 7.59
(m, 2H), 7.02 (dd, J = 3.7, 0.8 Hz, 1H), 3.88 (s, 3H); 13C {1H} NMR (101 MHz, DMSO-d6) δ 166.6, 137.3,
137.1, 135.4, 130.9, 130.4, 128.9, 127.2, 125.9, 125.5, 124.0, 113.6, 110.4, 52.6; HRMS (ESI) m/z calcd
for C16H14NO4S+ ([M+H]+): 316.0644, found: 316.0637.
4-phenyl-1-(phenylsulfonyl)-1H-pyrazole (1m). This compound was prepared according to a
similar method to 2a and the desired product was obtained after purification by silica gel column
chromatography (Heptane/EtOAc = 7:3). Light tan solid (366 mg, 77%); 1H NMR (400 MHz, DMSO-d6) δ
9.05 (d, J = 0.7 Hz, 1H), 8.46 (d, J = 0.7 Hz, 1H), 8.12 – 8.04 (m, 2H), 7.86 – 7.76 (m, 3H), 7.74 – 7.67 (m,
2H), 7.46 – 7.39 (m, 2H), 7.35 – 7.28 (m, 1H); 13C {1H} NMR (101 MHz, DMSO-d6) δ 144.3, 136.8, 135.7,
130.4, 130.4, 129.4, 128.9, 128.2, 128.1, 126.5, 126.0; HRMS (ESI) m/z calcd for C15H13N2O2S+ ([M+H]+):
285.0698, found: 285.0691.
4-(4-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrazole (1n). This compound was prepared according
to a similar method to 2a and the desired product was obtained after purification by silica gel column
chromatography (Heptane/EtOAc = 65:35). Off-white solid (338 mg, 92%); 1H NMR (400 MHz, DMSO-d6)
δ 9.06 (d, J = 0.8 Hz, 1H), 8.46 (d, J = 0.8 Hz, 1H), 8.13 – 8.01 (m, 2H), 7.92 – 7.78 (m, 3H), 7.77 – 7.67 (m,
2H), 7.35 – 7.16 (m, 2H); 13C {1H} NMR (101 MHz, DMSO-d6) δ 162.1 (d, J = 244.7 Hz), 144.3, 136.8, 135.7,
130.42, 128.9, 128.5 (d, J = 8.1 Hz), 128.1, 126.9 (d, J = 3.2 Hz), 125.1, 116.3 (d, J = 21.5 Hz); HRMS (ESI)
m/z calcd for C15H12FN2O2S+ ([M+H]+): 303.0604, found: 303.0596.
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