Trifluoroacetic acid → HCID 50915293, compound

Participants

Reaction Conditions

Reaction Steps

6-bromo-4-(tetrahydro-2H-pyran-4-ylmethoxy)-1-(4-methoxybenzyl)-3-(thiophen-2-yl)quinolin-2(1H)-one (160 mg, 0.30 mmol) was taken into neat trifluoroacetic acid (500 μL, 6.5 mmol). The reaction mixture was heated overnight at 100° C. The crude reaction mixture was poured into saturated sodium bicarbonate (50 mL). The product was extracted with dichloromethane (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, 4:1 dichlormethane/ethyl acetate) to yield 6-bromo-4-(tetrahydro-2H-pyran-4-ylmethoxy)-3-(thiophen-2-yl)quinolin-2(1H)-one as an off white solid. LCMS (M+H)=419.8. 1H NMR (400 MHz, CDCl3) 12.0 (s, 1H), 8.00 (s, 1H), 7.88 (d, 1H), 7.62 (d, 1H), 7.54 (d, 1H) 7.30 (d, 1H), 7.18 (t, 1H), 4M (dd, 2H) 3.65 (d, 2H), 3.45 (t, 2H), 2.15 (m, 1H), 1.75 (d, 2H), 1.4 (m, 2H).

Provenance & Evidence