反应详情

To a mixture of methyl 6-fluoro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (9.35 g, 24.64 mmol) and Cs2CO3 (24.08 g, 73.9 mmol) in N,N-dimethylformamide (100 mL) at room temperature was added iodoethane (3.98 mL, 49.3 mmol) slowly. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated aqueous NH4Cl and extracted with methylene chloride. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via column chromatography (ISCO, 120 g silica, 0-20% ethyl acetate/methylene chloride) to afford methyl 7-(ethyloxy)-6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (9.35 g, 93% yield). 1H NMR (400 MHz, DMSO-d6) 67.93-7.99 (m, 2H), 7.88 (d, J=7.78 Hz, 1H), 7.76 (t, J=7.65 Hz, 1H), 7.69 (d, J=8.53 Hz, 1H), 7.63 (d, J=12.30 Hz, 1H), 4.30 (q, J=7.03 Hz, 2H), 4.06 (s, 3H), 2.33 (s, 3H), 1.44 (t, J=6.90 Hz, 3H); MS (m/z) 408.1 (M+H+).

1. extractionextracted with methylene chloride
2. washThe combined organic extracts were washed with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe crude material was purified via column chromatography (ISCO, 120 g silica, 0-20% ethyl acetate/methylene chloride)