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

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Reaction Steps

A solution of methyl 3-methyl-6-(methylthio)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.5 g, 3.83 mmol) and 3-chloroperoxybenzoic acid (1.46 g, 8.43 mmol) in dichloromethane (50 mL) was stirred overnight. Saturated aqueous sodium bicarbonate and sodium sulfate were added and the mixture was stirred for 30 min. The aqueous mixture was extracted with methylene chloride (3 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, 10-40% ethyl acetate/hexanes) to afford methyl 3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.22 g, 75% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.31-8.39 (m, 2H), 8.26-8.31 (m, 1H), 8.00-8.08 (m, 2H), 7.93 (d, J=7.78 Hz, 1H), 7.80 (t, J=7.65 Hz, 1H), 4.12 (s, 3H), 3.40 (s, 3H), 2.42 (s, 3H); MS (m/z) 424.0 (M+H+).

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