Triethylamine → HCID 71042493, compound

Participants

Reaction Steps

To a solution of 4-bromo-8-fluoroquinoline-2-carboxylic acid (C6) (1.34 g, 4.96 mmol) in dichloromethane (20 mL) was added (1S,2S)-2-aminocyclohexanol (0.857 g, 7.44 mmol), benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (2.63 g, 5.95 mmol), and triethylamine (1.04 mL, 7.44 mmol). After 17 h, the mixture was diluted with dichloromethane and 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 0-3% methanol in dichloromethane to provide 4-bromo-8-fluoro-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (C7) that gave a mass ion (ES+) of 368.8 (81Br) for M+H+.

Provenance & Evidence