[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[N+:19]([O-])=O)(=[O:10])=[O:9])[CH:7]=1.[Sn](Cl)Cl.[OH-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[NH2:19])(=[O:10])=[O:9])[CH:7]=1The nitro intermediate (0.5 mmol) above was dissolved in EtOH (10 mL) and was treated with tin(II) chloride (2.5 mmol). The reaction mixture was heated to reflux for 12 h. The contents were cooled to RT and treated with 1 M aqueous NaOH until the pH of the reaction mixture was between 8-9 which resulted in formation of a precipate. The precipitate was then filtered, washed with methanol (10 mL) and DCM (10 mL). The combined filtrate was concentrated in vacuo and the residue obtained was purified by column chromatography eluting with DCM/ethyl acetate as eluant to give 115 mg of 5-bromo-N-(4-fluoro-2-aminophenyl)-2-methoxybenzenesulfonamide.
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