Ethyl bromoacetate → HCID 54678064, compound

Participants

Reaction Steps

To solution of 4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.090 g, 0.25 mmol) in acetone (20 mL) was added potassium carbonate (0.14 g, 1 mmol) and tetrabutyl-ammonium iodide (0.005 g, 0.5 mmol) at room temperature. After stirring for 30 min, bromo-acetic acid ethyl ester (0.083 g, 0.5 mmol) was then added into the reaction mixture and stirred for 16 h. The solvent was removed in vacuo, diluted with water (15 mL), extracted with ethyl acetate (3×30 mL), organics extracts washed with brine (15 mL), dried (Na2SO4), concentrated and purified on a RP-HPLC system. The title compound was one of the three reaction products that were purified. MS (ESI) m/e 416.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 12.44 (br s, 1H), 7.57 (d, J=7.98, 2H), 7.46 (d, J=8.29, 2H), 7.36–7.30 (m, 2H), 7.08–6.98 (m, 3H), 4.74 (s, 2H).

Provenance & Evidence