4-Bromobenzenesulfonamide → 4-(2-(8-Oxa-3-azabicyclo[3.2.1]octane-3-carbonyl)-4-(4-chlorophenyl)thiazol-5-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-oxa-3-azabicyclo[3.2.1]octan-3-yl(4-(4-chlorophenyl)thiazol-2-yl)methanone (Step 2 of compound 67, 0.7 g, 2.09 mmol) in dimethyl acetamide (10 ml) were added 4-bromobenzenesulfonamide (0.54 g, 2.30 mmol) and potassium acetate (0.41 g, 4.18 mmol) at 25° C. in a tube, the nitrogen gas was bubbled through reaction mixture for 15 minutes. To this was added palladium (II) acetate (0.047 g, 0.20 mmol) under nitrogen and the tube was sealed. 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 (100 ml). The reaction mixture was washed with water (2×30 ml), dried over sodium sulphate and concentrated under reduced pressure to obtain a crude product; which was purified by column chromatography over silica gel (100-200 mesh) using 35% ethyl acetate in hexanes as an eluent to obtain the title compound (0.2 g, 19.5%). MS: m/z 490 (M+1).

Provenance & Evidence