Ethyl bromoacetate → HCID 11720177, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of [6-Methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone (45 mg, 0.091 mmol) and potassium carbonate (40 mg, 0.29 mmol) in dry DMF (2.5 mL) was added ethyl bromoacetate (30 μL, 0.27 mmol) and the reaction heated to 70° C. for 2 h. After cooling to room temperature the reaction mixture was quenched with 10% NH4Cl(aq) (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was separated and washed with water (3×10 mL) and brine (10 mL), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude residue was purified by flash column chromatography (silica gel, eluent=2:1 hexane:ethyl acetate) to give the title compound as a yellow solid (44 mg, 98%). 1H-NMR (CDCl3) δ 8.28 (s, 1H), 8.06 (s, 1H), 7.13 (s, 2H), 7.10 (d, J=8.7 Hz, 1H), 7.04 (d, J=2.1 Hz, 1H), 6.79 (dd, J=8.7, 2.1 Hz, 1H), 4.91 (s, 2H), 4.23 (q, J=7.1 Hz, 2H), 3.93 (s, 3H), 3.86 (s, 3H), 3.77 (s, 6H), 1.27 (t, J=7.1 Hz, 3H).

Provenance & Evidence