[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[OH-].[K+].[I:15]I.S(=O)(=O)(O)[O-].[Na+]>CN(C=O)C>[I:15][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][CH:8]=1To a solution of 5-nitro-1H-indole (5 g, 30.86 mmol) in DMF (50 mL) was added KOH (5 g, 92.58 mmol), followed by addition of I2 (15.7 g, 61.74 mmol). The reaction mixture was stirred at RT for 2 h and then added 10% aqueous sodium bisulfate (50 mL) solution. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to obtain the title compound as a pale yellow solid (8.0 g. 91%). MS (ESI, pos. ion) m/z: 286.9 (M−1)
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