Methanol → Methyl 2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxylate

Participants

Reaction Steps

A mixture of the 6-bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline (950 mg, 3.0 mmol), triethylamine (1.25 ml, 9.0 mmol), 1,3-bis(diphenylphosphino)propane (123 mg, 0.3 mmol), palladium acetate (67 mg, 0.3 mmol) and methanol (4.8 ml) in DMF (10 ml) was stirred at reflux under carbon monoxide (1 atm) for 16 hours. Then the reaction was quenched with saturated sodium bicarbonate aqueous solution and the product was extracted with ethyl acetate and dried over sodium sulfate. Then, filtration, evaporation, purification through silica gel column chromatography eluting with hexane/ethyl acetate (25:1) furnished the title compound (777 mg, 88% yield) as a white solid. 1H NMR (300 MHz, CDCl3) ppm 1.74 (6H, s), 4.00 (3H, s), 7.71 (1H, d, J=8.8 Hz), 8.14 (1H, d, J=8.8 Hz), 8.25 (1H, d, J=8.8 Hz), 8.28-8.32 (1H, m), 8.58-8.59 (1H, m). MS (ESI): m/z 298 (M+H)+.

Provenance & Evidence