Cesium carbonate → HCID 118114785, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-tert-butyl 1-(5-bromo-6-cyanopyridin-3-yl)piperidin-3-ylcarbamate (95) (300 mg, 0.78 mmol), (4-aminophenyl)(morpholino)methanone (322 mg, 1.56 mmol), Pd2(dba)3 (73 mg, 0.08 mmol), XantPhos (93 mg, 0.16 mmol), fine powder Cs2CO3 (765 mg, 2.34 mmol) in dioxane (50 mL) was degassed with nitrogen stream for 3 min. The mixture was stirred in a nitrogen atmosphere at 115° C. for 2 h. The mixture was cooled, diluted with 200 mL EtOAc, filtered through celite, and concentrated in vacuo. The residue was subjected to flash column chromatography with 20 to 100% EtOAc in DCM to isolate (R)-tert-butyl 1-(6-cyano-5-(4-(morpholine-4-carbonyl)phenylamino)pyridin-3-yl)piperidin-3-ylcarbamate (96) (yield >80%).

Provenance & Evidence