[I:1]Cl.C(Cl)Cl.[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([F:16])[CH:15]=1)[NH:12][CH:11]=[CH:10]2.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1.C1(C)C=CC=CC=1.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:17]1([S:23]([N:12]2[C:13]3[C:9](=[CH:8][C:7]([F:6])=[CH:15][C:14]=3[F:16])[C:10]([I:1])=[CH:11]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1The 1.0 M ICl in CH2Cl2 (43 ml, 43 mmol) is added to a solution of 5,7-difluoro-indole (6 g, 39 mmol) in 35 ml pyridine under N2 at 0° C. and the resulting mixture is stirred for 30 minutes. The reaction is diluted with toluene and washed with brine, 1N HCl, 1N NaOH, dried (Na2SO4), filtered and concentrated. The crude 3-iodo-5,7-difluoroindole is stirred in toluene (85 ml) and 5 N NaOH (70 ml), tetrabutylammonium bromide (1.25 g, 3.9 mmol), then benzenesulfonyl chloride (6.2 ml, 48 mmol) are added and the resulting mixture is stirred 24 hours. The two phase reaction mixture is diluted with toluene, washed with brine, dried (Na2SO4), filtered, concentrated and the residue is triturated with diethyl ether/petroleum ether. The resulting solid is filtered to give 14.2 g of N-Benzenesulfonyl-3-iodo-5,7-difluoroindole (87%).
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