Potassium Carbonate → HCID 86682939, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-6-chloro-2-isopropyl-quinoline-3-carboxylic acid methyl ester (150 mg, 0.44 mmol), K2CO3 (183 mg, 1.31 mmol) and 3-trifluoromethoxyphenylboronic acid (61 mg, 0.35 mmol) in dimethyl formamide (4 ml) in a sealed tube was purged with argon for 20 min followed by addition of Pd(PPh3)4 (51 mg, 0.04 mmol), again purged with argon for 10 min and the reaction mixture was heated at 90° C. for 5 h under stirring. After cooling, the reaction mixture was filtered through celite bed and washed with ethyl acetate. The organic phase was concentrated in vacuo and then partitioned between water and ethyl acetate. The organic phase was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo to afford a crude residue. This crude residue was purified by flash column chromatography (100-200 mesh silica, eluting with 2% EtOAc in hexane) to afford pure 6-chloro-2-isopropyl-4-(3-trifluoromethoxy-phenyl)-quinoline-3-carboxylic acid methyl ester (65 mg, 35%) as pale yellow sticky liquid. LC-MS: 424 (M+H)+.

Provenance & Evidence