Sodium Thiosulfate → Methyl 3-methyl-7-(methyloxy)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

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A solution of methyl 3-methyl-7-(methyloxy)-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (4.5 g, 8.54 mmol) and 3-chloroperoxybenzoic acid (3.85 g, 17.17 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous NaHCO3 and Na2S2O3 were added slowly and the resulting mixture was stirred for 30 min. The mixture was extracted with methylene chloride (3 times). The combined organic extracts were washed with brine (2 times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-15% ethyl acetate/methylene chloride) to give methyl 3-methyl-7-(methyloxy)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.74 g, 71% yield). 1H NMR (400 MHz, DMSO-d6) δ8.25 (s, 1H), 7.99-8.06 (m, 2H), 7.92 (d, J=7.78 Hz, 1H), 7.82 (s, 1H), 7.76-7.82 (m, 1H), 4.11 (s, 3H), 4.09 (s, 3H), 3.41 (s, 3H), 2.38 (s, 3H); MS (m/z) 454.1 (M+H+).

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