Iodoethane → HCID 67383776, compound

Participants

Reaction Steps

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+).

Provenance & Evidence