Potassium Carbonate → HCID 11261037, compound

Participants

Reaction Steps

A solution of 4-(3-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (Example 42, 1.0 g, 2.5 mmol), methyl 4-bromomethylbenzoate (0.57 g, 2.5 mmol) and K2CO3 (1.38 g, 10 mmol) in acetone (25 ml) was heated to reflux. After 2 hr, the reaction was cooled, filtered and concentrated. The resulting oil was taken up into THF/MeOH (20 ml) and 2N NaOH (2 ml) was added and the reaction was refluxed. After 2 hr, the reaction was cooled, poured into 2N HCl and extracted with EtOAc. The EtOAc was dried concentrated and the product was purified by column chromatography (eluent 40% EtOAc/hexane) to give the desired product as a foam (1.00 g, Yield=77%); MS (ESI) m/z 528 ([M+H]+); 1H NMR (DMSO) δ 12.97 (s, 1H), 9.14 (s, 1H), 8.33 (d, 1H, J=6.6 Hz), 7.94-7.88 (m, 3H), 7.76 (t, 1H, J=8.0 Hz), 7.63 (d, 2H, J=7.1 Hz), 7.54-7.47 (m, 1H), 7.46 (d, 2H, J=8.5 Hz), 7.37-7.33 (m, 2H), 7.27 (t, 1H, J=7.8 Hz), 7.05-6.98 (m, 2H), 6.87 (m, 1H),

Provenance & Evidence