Tetrahydrofuran → HCID 67383892, compound

Participants

Reaction Steps

To a solution of methyl 7-(ethyloxy)-6-(ethylthio)-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (10.32 g, 22.95 mmol) in tetrahydrofuran (150 mL) was added oxone (35.3 g, 57.4 mmol) in water (75 mL). The resulting mixture was stirred overnight at room temperature. The mixture was diluted with water and extracted with methylene chloride. The combined organic extracts were washed with brine, 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 7-(ethyloxy)-6-(ethylsulfonyl)-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (9.11 g, 82% yield). 1H NMR (400 MHz, DMSO-d6) δ8.24 (s, 1H), 7.98-8.05 (m, 2H), 7.92 (d, J=7.78 Hz, 1H), 7.76-7.82 (m, 2H), 4.39 (q, J=6.94 Hz, 2H), 4.09 (s, 3H), 3.56 (q, J=7.28 Hz, 2H), 2.36 (s, 3H), 1.45 (t, J=6.90 Hz, 3H), 1.14 (t, J=7.40 Hz, 3H); MS (m/z) 482.1 (M+H+).

Provenance & Evidence