Potassium Carbonate → HCID 66857786, compound

Participants

Reaction Steps

To a solution of 6-bromo-4-hydroxy-1-(4-methoxybenzyl)-3-(thiophen-2-yl)quinolin-2(1H)-one (1.2 g, 2.8 mmol) in tetrahydrofuran (0.3 M, 10 mL) at room temp was added potassium carbonate (1.2 g, 8.4 mmol). 4-bromomethyl tetrahydropyran (1.0 g, 5.6 mmol) was added to this solution mixture. The reaction mixture was left stirring overnight. The crude reaction mixture was poured into 1 N sodium hydroxide (100 mL). The product was extracted with ethyl acetate (3×50 mL). The combined organic extractions were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 7:3 hexanes/ethyl acetate) to yield 6-bromo-4-(tetrahydro-2H-pyran-4-ylmethoxy)-1-(4-methoxybenzyl)-3-(thiophen-2-yl)quinolin-2(1H)-one as an orange oil. LCMS (M+H)=539.8.

Provenance & Evidence