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

Beteiligte Stoffe

Reaktionsschritte

Sodium hydride (1.27 g, 31.6 mmol) was added portionwise to a suspension of 6-fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (8.0 g, 21.09 mmol) in dimethyl sulfoxide (50 mL). The mixture was stirred for 20 min. Sodium ethanethiolate (2.168 g, 23.20 mmol) was added and the resulting mixture was stirred at 100° C. for 1 h. The mixture was cooled to room temperature, iodomethane (3.96 mL, 63.3 mmol) was added, and the mixture was stirred for 2 h. The reaction mixture was diluted with water and was extracted with methylene chloride (three times). The combined organic extracts were washed with brine (two times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 330 g silica, 0-10% ethyl acetate/methylene chloride) to afford methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (7.05 g, 77% yield, about 70% pure). MS (m/z) 436.1 (M+H+).

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