Tetrahydrofuran → 2-(3-Cyclohexyl-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

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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 ethyl ester (0.41 g, 1.0 mmol), cyclohexylzinc bromide solution 0.5 M in tetrahydrofuran (3.0 mL, 1.5 mmol), 1,1′-bis(diphenylphosphino) ferrocenedichloropalladium (II) (41 mg, 0.05 mmol), and DMF (0.5 mL) in dioxane (3 mL) was stirred at 70° 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)(10% ethyl acetate/hexanes) to afford 2-(3-cyclohexyl-5-fluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.21 g, 51%) as a white solid: LC/MS m/e calcd for C26H32FNO2 M+: 410.6, observed: 410.1.

Provenance & Evidence