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

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A solution of methyl 6-(ethylthio)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (7.05 g, 11.33 mmol) and 3-chloroperoxybenzoic acid (5.11 g, 22.78 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous NaHCO3 and Na2S2O3 were added slowly. The mixture was stirred for 30 min and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified via column chromatography (ISCO, 0-15% ethyl acetate/methylene chloride) to give methyl 6-(ethylsulfonyl)-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (3.4 g, 64% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.98-8.05 (m, 2H), 7.92 (d, J=8.03 Hz, 1H), 7.76-7.85 (m, 2H), 4.10 (s, 3H), 4.09 (s, 3H), 3.54 (q, J=7.53 Hz, 2H), 2.37 (s, 3H), 1.15 (t, J=7.40 Hz, 3H); MS (m/z) 468.1 (M+H+).

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