Cesium carbonate → 1-[5-Chloro-8-(3-methoxypyrrolidin-1-yl)quinolin-7-yl]ethanone

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.34 mmol, from Example 47, Step 2), 3-methoxypyrrolidine hydrochloride (0.056 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0068 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 mg, 0.010 mmol), and cesium carbonate (0.33 g, 1.0 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane) to give the desired product (44.5 mg, 43%). LCMS calculated for C16H18ClN2O2 (M+H)+: m/z=305.1; Found: 305.1.

Provenance & Evidence