Cesium carbonate → HCID 89923126, compound

Participants

Reaction Conditions

Reaction Steps

2-chloro-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (170 mg, 0.479 mmol), 5-amino-4-chloro-2-(3-oxopropyl)benzonitrile (100 mg, 0.479 mmol, Example 566A), palladium(II) acetate (32.3 mg, 0.144 mmol), DPPF (26.6 mg, 0.048 mmol), Xantphos (27.7 mg, 0.048 mmol), and cesium carbonate (312 mg, 0.958 mmol) were combined in a 50 ml round bottom flask and dioxane (4 mL) was added. The flask was evacuated and backfilled with N2 3×, then heated at 100° C. for 2 h. The reaction was cooled to room temperature and filtered through celite, rinsing with EtOAc. The solvent was removed in vacuo and the material was purified by flash column chromatography (0-80% EtOAc/Hex; 40 g column). 2-((2-chloro-5-cyano-4-(3-oxopropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (49 mg) was obtained.

Provenance & Evidence