4-Bromobenzenesulfonamide → 4-(2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-(2,4-difluorophenyl)thiazol-5-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-(2,4-difluorophenyl)thiazole (Step 2 of compound 66, 0.23 g, 0.82 mmol) in dimethyl acetamide (5 ml) were added 4-bromobenzenesulfonamide (0.21 g, 0.90 mmol) and potassium acetate (0.16 g, 1.65 mmol) at 25° C. in a tube, the nitrogen gas was bubbled through reaction mixture for 15 minutes. To the reaction mixture was added palladium (II) acetate (0.019 gm, 0.08 mmol) under nitrogen and the reaction mixture was heated at 150° C. for 15 hr with stirring. The progress of reaction was monitored by TLC. The reaction mixture was cooled to 25° C. and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 ml). The reaction mixture was washed with water (2×10 ml), dried over sodium sulphate and concentrated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (0.088 g, 24.5%). MS: m/z 434 (M+1).

Provenance & Evidence