Cesium carbonate → HCID 59276262, compound

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 3-(2-(4-cyanophenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)piperidine-1-carboxylate. To an orange solution of 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzonitrile (0.250 g, 0.796 mmol) in dioxane (10 mL) was added (5)-tert-butyl 3-aminopiperidine-1-carboxylate (0.319 g, 1.592 mmol), cesium carbonate (0.519 g, 1.592 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.092 g, 0.159 mmol) and tris(dibezylideneacetone)palladium (0.077 g, 0.084 mmol) at room temperature under nitrogen. The reaction mixture was heated at 100° C. for 1.5 h under nitrogen. Upon completion of the reaction as indicated by LCMS the reaction mixture was poured into brine, and extracted with ethyl acetate several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by column chromatography (eluting with 0-80% ethyl acetate in hexanes) to give the title compound as a tan solid (0.122 g, 35% yield). MS (ESI) m/z 434.51 [M+1]+.

Provenance & Evidence