Cesium carbonate → 1-[5-Chloro-8-(4-phenoxypiperidin-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), 4-phenoxypiperidine hydrochloride (0.087 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0067 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 g, 0.010 mmol), and cesium carbonate (0.42 g, 1.3 mmol) in tetrahydrofuran (4 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, evaporated and purified on silica gel (eluting with 100% dichloromethane) to give the desired product (23.6 mg, 18%). LCMS calculated for C22H22ClN2O2 (M+H)+: m/z=380.1; Found: 381.1.

Provenance & Evidence