Cesium carbonate → 2-((2-Chloro-5-cyano-3-(prop-1-en-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-4-chloro-5-(prop-1-en-2-yl)benzonitrile (367 mg, 1.91 mmol), 2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (676 mg, 1.91 mmol), Cs2CO3 (1.24 gm, 3.81 mmol), DPPF (106 mg, 0.191 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (110 mg, 0.191 mmol) and Pd(OAc)2 (128 mg, 0.572 mmol) in a microwave vial that was flushed with nitrogen. Dioxane (16 mL) was added and the vial was sealed and heated at 100° C. for 4 hr. The reaction was diluted with EtOAc and filtered through celite. The solvent was removed from the filtrate and radial silica gel chromatography eluting with hexane containing 5 to 40% EtOAc afforded 2-((2-chloro-5-cyano-3-(prop-1-en-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (748 mg) as a solid.

Provenance & Evidence