Hydrochloric Acid → 1-[4-(5-acetyl-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

Participants

Reaction Steps

A mixture of 1-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (200 mg, 0.4 mmol), 1-vinyloxybutane (0.26 mL, 2.0 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), 1,3-bis(diphenylphosphino) propane (DPPP) (10.5 mg, 0.03 mmol), K2CO3 (66.34 mg, 0.48 mmol), and water (0.1 mL) in DMF (1 mL) was microwaved for 1 hour at 122° C. After cooling, the mixture was poured into 5 mL of 5% HCl, stirred for 30 minutes and extracted with three 10 mL portions of ethyl acetate. The combined organic layers were washed with 10% aqueous K2CO3 and dried. The residue was purified silica gel chromatography and then by reverse phase HPLC to yield 50 mg (27% yield) of 1-[4-(5-acetyl-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one as white solid.

Provenance & Evidence