Dichloromethane → HCID 86726470, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-8-fluoro-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (C7) (1.88 g, 5.12 mmol) in 10:1 THF:H2O (22 mL) was added potassium vinyltrifluoroborate (2.06 g, 15.4 mmol) and cesium carbonate (3.34 g, 10.2 mmol). The reaction was placed under N2(g), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium(II), complex with dichloromethane (0.100 g, 0.122 mmol) was added. The mixture was heated to 100° C. for 3 h, then cooled to RT and diluted with ethyl acetate. The organic solution was washed with saturated aqueous sodium bicarbonate (1×) and brine (1×), dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography eluting with 0-5% methanol in dichloromethane to provide 4-ethenyl-8-fluoro-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (C8) that gave a mass ion (ES+) of 315.1 for M+H+.

Provenance & Evidence