Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([F:13])[F:12].[CH3:14][S:15]([O-:17])=[O:16].[Na+].CNCCNC>CS(C)=O>[F:12][C:5]1([F:13])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([S:15]([CH3:14])(=[O:17])=[O:16])[CH:3]=2)[NH:7][C:6]1=[O:11]To a stirred solution of 5-bromo-3,3-difluoroindolin-2-one (5.0 g, 20 mmol) in DMSO (50 mL), sodium methanesulfinate (3.0 g, 30 mmol), copper(I) trifluoromethane-sulfonate benzene complex (1.52 g, 3.022 mmol) and N,N′-dimethylethylenediamine (0.33 mL, 3.022 mmol) were added and stirred at 120° C. for 14 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and resulting residue was purified by flash column chromatography to give the title product (2.9 g, 58.2%); MS: 247.9 (M+1).
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