Water → HCID 59321487, compound

Participants

Reaction Steps

Cesium carbonate (62.6 mg, 192.2 μmol) was added to ethyl 7-fluoro-6-(4-hydroxyphenyl)-2-quinolinecarboxylate (54.4 mg, 174.7 μmol) and 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole (58.6 mg, 192.2 μmol) in N,N-dimethylformamide (1.7 mL) at room temperature. The resulting suspension was stirred for 68 hours, then water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 3:7 ethyl acetate:hexanes to give 49.4 mg (49%) of ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-7-fluoro-2-quinolinecarboxylate as an oil. 1H NMR (400 MHz, d6-DMSO): δ 8.61 (d, J=9 Hz, 1H), 8.23 (d, J=9 Hz, 1H), 8.11 (d, J=9 Hz, 1H), 8.02 (d, J=12 Hz, 1H), 7.65-7.62 (m, 2H), 7.56 (d, J=7 Hz, 2H), 7.56-7.52 (m, 1H), 6.96 (d, J=9 Hz, 2H), 4.90 (s, 2H), 4.42 (q, J=7 Hz, 2H), 3.48 (septet, J=7 Hz, 1H), 1.38 (t, J=7 Hz, 3H), 1.34 (d, J=7 Hz, 6H). ESI-LCMS m/z 579 (M+H)+.

Provenance & Evidence