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

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.4 g, 6.61 mmol) and sodium thiomethoxide (1.158 g, 16.52 mmol) in N,N-dimethylformamide (40 mL) was stirred at 100° C. overnight. The mixture was cooled to room temperature, treated with NaH (0.264 mg, 6.61 mmol), and stirred for 20 min. Methyl iodide (1.5 g, 9.92 mmol) was added, and the mixture was stirred for 2 h. The mixture was diluted with water and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 120 g Silica, 0-30% ethyl acetate/hexanes) to afford methyl 3-methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.54 g, 95% yield). MS (m/z) 392.1 (M+H+).

Provenance & Evidence