4-Bromobenzenesulfonamide → (cis) 4-(4-(4-Chloroindolin-1-yl)-2-(2,6-dimethylmorpholine-4-carbonyl) thiazol-5-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (cis) (4-(4-chloroindolin-1-yl)thiazol-2-yl) (2,6-dimethylmorpholino) methanone (Step-2, of compound 45, 0.6 g, 1.59 mmol in dimethyl acetamide (10 ml) were added 4-bromobenzenesulfonamide (0.41 g, 1.75 mmol) and potassium acetate (0.31 g, 3.18 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 (0.03 g, 0.16 mmol) under nitrogen and the tube was sealed. The reaction mixture was heated at 150° C. for 18 hr under 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 (30 ml), 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 preparative HPLC to obtain the title compound (0.22 g, 26.0%). MS: m/z 533 (M+1).

Provenance & Evidence