Cesium carbonate → 5-chloro-8-[(3R)-3-hydroxypyrrolidin-1-yl]-N-methoxy-N-methylquinoline-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (0.150 g, 0.376 mmol), (3R)-pyrrolidin-3-ol (0.0394 g, 0.452 mmol, Aldrich), palladium acetate (2 mg, 0.008 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (7 mg, 0.01 mmol), and cesium carbonate (0.343 g, 1.05 mmol) in tetrahydrofuran (4 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane, washed with brine, dried over sodium sulfate, and evaporated to dryness. The resultant residue was purified on silica gel, eluting with 0 to 10% MeOH in dichloromethane, to give the desired product (115 mg, 91%). LCMS calculated for C16H19ClN3O3(M+H)+: m/z=336.1; found: 336.1.

Provenance & Evidence