Cesium carbonate → HCID 89922656, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-(3-amino-2-chloro-5-cyanophenyl)-3-hydroxyazetidine-1-carboxylate (Example 647B) (37.4 mg, 0.116 mmol), 2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (49.2 mg, 0.139 mmol), DPPF (6.40 mg, 0.012 mmol), Cs2CO3 (75 mg, 0.231 mmol), XANTPIIOS (6.68 mg, 0.012 mmol), and palladium(II) acetate (7.78 mg, 0.035 mmol) in a microwave vial in dioxane (1 mL) was evacuated and backfilled with nitrogen for 3 times, then the mixture was heated in an oil bath at 100° C. for 3 hours. The reaction mixture was diluted with EtOAc, washed with water, brine, and dried over Na2SO4. Removal of the solvent and the crude material was purified by radial silica gel chromatography eluting with hexane containing 10 to 40% EtOAc to afford 40.5 mg of tert-butyl 3-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxyazetidine-1-carboxylate

Provenance & Evidence