Pyridine → N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-(chloromethyl)-1,3-thiazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

A three necked rounded bottomed flask was charged with 6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amine (12.7 g), anhydrous DCM (100 ml) and pyridine (7.5 ml) then placed under a nitrogen atmosphere and cooled to −10° C. A suspension of 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (9.39 g) in anhydrous DCM (75 ml) was added in one portion. The reaction mixture was stirred at room temperature for ˜4 hrs. Additional 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (1.36 g) in anhydrous DCM was added in one portion and the reaction was stirred overnight. The suspension was filtered, washing sparingly with DCM, then dried on the vacuum pump to give title compound (15.8 g).

Provenance & Evidence