Sodium hydride → HCID 68312811, compound

Participants

Reaction Steps

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol from Example 4 (465 mg, 1.429 mmol) in DMF (8 mL) was added sodium hydride (57.2 mg, 60% in oil, 1.429 mmol). The mixture was stirred at RT for 15 min, then a solution of 2-bromo-2-isobutylmalonic acid diethyl ester (633 mg, 2.14 mmol) in DMF (1 mL) was added. The reaction mixture was stirred at 70° C. for 4 h. The cooled reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% MeOH in DCM) affording the title compound (0.39 g, 51%). LCMS (Method B): RT 3.96 min [M+H]+ 540.

Provenance & Evidence