Cesium carbonate → tert-butyl 5-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

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 (263 mg, 0.741 mmol), tert-butyl 5-(3-amino-2-chloro-5-cyanophenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (266 mg, 0.706 mmol), palladium(ii) acetate (42.0 mg, 0.187 mmol), xantphos (40.8 mg, 0.071 mmol), DPPF (39.1 mg, 0.071 mmol) and cesium carbonate (598 mg, 1.835 mmol) in dioxane (10 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 tert-butyl 5-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (360 mg) as a foaming solid.

Provenance & Evidence