Cesium carbonate → tert-butyl 1-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yl)piperidin-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a reaction vial was added 6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yl trifluoromethanesulfonate (30 mg, 0.0551 mmol; prepared according to Example 24, Step A), tert-butyl piperidin-4-ylcarbamate (22.1 mg, 0.110 mmol) and cesium carbonate (53.9 mg, 0.165 mmol). Toluene (2 mL) was added and argon was bubbled through the mixture for 10 minutes. To this mixture was added rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.86 mg, 0.0110 mmol) and tris(dibenzylideneacetonyl)bis-palladium (5.05 mg, 0.00551 mmol). The reaction mixture was heated at 90° C. for 4 hours. The mixture was filtered through Celite®, washing with dichloromethane and methanol. The solution was concentrated under a stream of nitrogen and the residue was purified by preparative thin layer chromatography on silica, eluting with 10% methanol in dichloromethane containing 0.5% ammonium hydroxide solution to give tert-butyl 1-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yl)piperidin-4-ylcarbamate (14.6 mg).

Provenance & Evidence