Ethyl bromoacetate → HCID 67210036, compound

Participants

Reaction Steps

NaH (0.115 g, 2.886 mmol) was added to an ice cold solution of 1-methyl-3-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (0.325 g, 1.443 mmol) in DMF (5.0 mL) and stirred at ambient temperature for 30 min. Ethyl bromoacetate (0.482 g, 2.886 mmol) was added to the reaction mixture dropwise and stirring was continued for 2 h. After completion of the reaction, the excess of NaH was quenched by the addition of ice cold water. Diethyl ether was added and the mixture was extracted with water and brine. The organic layer was dried over Na2SO4 and filtered. Concentration of the organic layer furnished the title compound as a white solid (0.353 g, 79%). [1H-NMR (CDCl3, 300 MHz) δ 8.2 (d, 1H), 7.94-7.87 (m, 2H), 7.54-7.36 (m, 3H), 6.79 (d, 1H), 5.0 (s, 2H), 4.29 (q, 2H), 4.05 (s, 3H), 1.30 (t, 3H); HPLC RtA=5.555 min (95%); LCMS RtC=1.967 min; [M+H]+=312.1]

Provenance & Evidence