Sodium hydride → HCID 68313075, 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 (100 mg, 0.307 mmol) in DMF (2 mL) was added sodium hydride (12.3 mg, 60% in oil, 0.307 mmol). The mixture was stirred at RT (room temperature) for 15 min, then 2-bromo-2-methylmalonic acid diethyl ester (88 μL, 0.461 mmol) was added. The reaction mixture was stirred at RT for 45 min, and then partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic layers 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 2-8% MeOH in DCM) affording the title compound as a colourless gum (148 mg, 97%). LCMS (Method B): RT 3.46 min [M+H]+ 498.

Provenance & Evidence