[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:25]=[CH:24][C:18]2[NH:19][C:20]([CH2:22]Cl)=[N:21][C:17]=2[CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:25]=[CH:24][C:18]2[NH:19][C:20]([CH2:22][O:34][C:31]3[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:35])[F:36])=[CH:33][CH:32]=3)=[N:21][C:17]=2[CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]A mixture of N-tert-butyl-2-(2-chloromethyl-1H-benzoimidazol-5-yl)benzenesulfonamide (100 mg, 0.26 mmol), α,α,α-trifluoro-p-cresol (43.0 mg, 0.26 mmol), Na2CO3 (28.1 mg, 0.26 mmol), Cs2CO3 (86.5 mg, 0.26 mmol), and catalytic KI (1.5 mg, 0.009 mmol) in acetone (2 mL) was refluxed for 12 h. The reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography (silica, EtOAc: hexanes, 1:1) to afford the title compound as an off-white solid (40.1 mg, 30% yield). Calcd. For C25H24F3N3O3S: 504.54 (M+H), Found 504.2.
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