Potassium Hydroxide → HCID 67440892, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-bromo-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (0.41 g, 1.0 mmol), 1-isopropyl piperazine (0.64 g, 5.0 mmol), copper (I) iodide (120 mg, 0.6 mmol), L-proline (69 mg, 0.6 mmol) and potassium hydroxide (33.6 mg, 0.6 mmol) in DMSO (2 mL) was stirred at 120° C. for 2 hours. Then treated with saturated ammonium chloride (20 mL), extracted with ether (100 mL). After removal of solvent, the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company)(40% ethyl acetate/hexanes) to afford 2-[3-fluoro-5-(4-isopropyl-piperazin-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.27 g, 60%) as a white solid: LC/MS m/e calcd for C27H36FN3O2 (M+H)+: 454.6, observed: 454.3.

Provenance & Evidence