Water → 2-(Chloromethyl)-N-[6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

To solution of 6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-amine (1.5 g, 3.86 mmol) in chloroform (20 ml) at 0° C. was added DIPEA (1.35 ml, 7.72 mmol). 2-(Chloromethyl)-1,3-thiazole-4-carbonyl chloride (1.8 g, 6.98 mmol) in chloroform (20 ml) was added dropwise and the mixture was stirred at 0° C. for 1 h 15 mins. The mixture was allowed to warm to room temperature and stirring continued for 18 h. A further portion of 2-(chloromethyl)-1,3-thiazole-4-carbonyl chloride (0.2 g, 1.02 mmol) was added to the mixture which was stirred at room temperature for 30 mins. Water (50 ml) was added to quench the reaction and the mixture was extracted with DCM (2×100 ml), separating the layers using a hydrophobic frit. The organics were collected and solvent removed in vacuo to give a brown solid which was triturated with ether (10 ml). The solid was filtered off and dried in a vacuum oven overnight to afford the title compound (1.6 g).

Provenance & Evidence