Cesium carbonate → HCID 89923091, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (47.2 mg, 0.133 mmol), (S)-3-amino-4-chloro-5-((4-(2,4-dimethoxybenzyl)morpholin-3-yl)methoxy)benzonitrile (53 mg, 0.127 mmol), palladium(ii) acetate (7.55 mg, 0.034 mmol), Xantphos (7.34 mg, 0.013 mmol), DPPF (7.03 mg, 0.013 mmol) and cesium carbonate (107 mg, 0.330 mmol) in dioxane (1 ml) was evacuated and back filled with nitrogen three time and was heated at 80° C. for 10 h. The reaction mixture was filtered through a celite pad and the filtrate was concentrated. the crude product was purified by flash chromatography on silica gel using an automated ISCO system (80 g column, eluting with 5-40% ethyl acetate/hexanes) to give (S)-2-((2-chloro-5-cyano-3-((4-(2,4-dimethoxybenzyl)morpholin-3-yl)methoxy)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (80 mg) as a light yellow solid.

Provenance & Evidence