Methyl iodide → Methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2 g, 4.40 mmol) in N-methyl-2-pyrrolidone (15 mL) and DMSO (30 mL) was added copper(I) iodide (2.52 g, 13.21 mmol) followed by ethanesulfinic acid, sodium salt (1.534 g, 13.21 mmol). The mixture was evacuated and purged with N2 three times and heated at 120° C. for 16 h. The mixture was cooled to room temperature, and iodomethane (1.377 mL, 22.01 mmol) was added. After 90 min, additional iodomethane (1.377 mL, 22.01 mmol) was added and the mixture was stirred for an additional hour. The mixture was diluted with methylene chloride and water, and the biphasic solution was filtered through Celite®. The phases were separated, and the aqueous phase was extracted with methylene chloride (50 mL). The combined organic extracts were washed with water (3×50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was loaded onto florisil and purified via column chromatography (ISCO, 40 g silica, 5-55% ethyl acetate/hexanes) to give methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.95 g, 76% yield). MS (m/z) 468.0 (M+H+).

Provenance & Evidence