Sodium hydride → HCID 54751409, compound

Participants

Reaction Steps

6-(3-(1,3-Dioxan-2-yl)propanoyl)-2-bromo-7-hydroxy-4-methylthieno[3,2-b]pyridin-5(4H)-one. To ethyl 2-bromo-7-hydroxy-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxylate (800 mg, 2408 μmol, prepared in a manner similar to that described in Method 7 using methyl 5-bromo-3-(methylamino)thiophene-2-carboxylate (Method 6(b))) was added THF (24 mL) and sodium hydride (60% in oil; 963 mg, 24084 μmol). The resulting mixture was stirred for 1 hour at ambient temperature. 2-[2-(1,3-Dioxanyl)]ethylmagnesium bromide in THF (4.81 mL, 2408 μmol) was then added dropwise at ambient temperature, and the resulting mixture was stirred for 3 hours before it was quenched with water, acidified with 5 N HCl, filtered, washed with water, and dried in a vacuum oven. The crude product was purified via HPLC to give the title compound.

Provenance & Evidence