[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2.[OH-].[K+].[I:20]I.O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[I:20]To a solution of 5-(2,6-difluoro-phenyl)-1H-indazole (40.8 g, 176.46 mmol) in DMF (441.1 mL) was added KOH (14.8 g, 246.69 mmol) and I2 (98.5 g, 388.21 mmol) at RT. The reaction mixture was stirred for 6 h at RT. Water was added to the reaction mass and extracted with EtOAc (2×500 mL). Organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated and purified by column using silica (100-200 mesh) and 0-15 EtOAc-hexane to provide 5-(2,6-difluoro-phenyl)-3-iodo-1H-indazole (45.5 g, 72.4% yield). MS (ESI, pos. ion) m/z: 357.1 (M+1).
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