Cl([O-])=O.[Na+].[CH:5]([C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:24]#[N:25])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1)=[O:6].O.P([O-])([O-])([O-])=[O:28].[Na+].[Na+].[Na+].OO.S([O-])([O-])=O.[Na+].[Na+].Cl>O.CC#N>[C:24]([C:12]1[CH:11]=[C:10]2[C:15]([C:7]([C:5]([OH:28])=[O:6])=[CH:8][NH:9]2)=[CH:14][C:13]=1[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)#[N:25]
A solution of sodium chlorite (8.1 mg, 0.072 mmol) in water (2 mL) was added dropwise to a solution of 3-formyl-5-(4-methoxy-phenyl)-1H-indole-6-carbonitrile (50.0 mg, 0.18 mmol), sodium phosphate monohydrate (5.60 mg, 0.04 mmol) and 25% hydrogen peroxide (25.9 mg, 0.19 mmol) in MeCN (2 mL) and water (1 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes, and warmed to room temperature. Additional sodium chlorite (16.2 mg, 0.144 mmol) and MeCN (5 mL) were added, and the reaction mixture was stirred at room temperature for another 16 hours. The reaction was quenched with sodium sulfite (46.6 mg, 0.362 mmol) and acidified with concentrated HCl (1 mL) to form precipitates. The solid was filtered, washed with water (5 mL) and air dried to give the title compound (14 mg, 26% yield). MS (ES−) 291.1 (M−1)−. 1H NMR (400 MHz, DMSO-d6) δ 12.35 (br. s., 1H), 12.14 (br. s, 1H), 8.29 (d, J=2.73 Hz, 1H), 8.07 (s, 1H), 8.04 (s, 1H), 7.50 (d, J=8.20 Hz, 2H), 7.08 (d, J=8.39 Hz, 2H), 3.83 (s, 3H).
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