Water → N-(4-Chlorobenzyl)-4-ethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-(4-chlorobenzyl)-7-hydroxythieno[3,2-b]pyridine-6-carboxamide (Example 1, 885 mg)was dissolved in DMF (20 mL) and to the solution was added potassium carbonate (1.92 g) and iodoethane (1.1 mL). The mixture was heated to 100° C. for 16 h. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with water (3×25 mL) followed by brine (25 mL), dried (MgSO4), and concentrated. The crude product was purified by column chromatography (EtOAc/heptane, 1/1; CH2Cl2/methanol, 100/1) and the resulting solid was recrystallized from ethanol to afford 590 mg of the title compound as a white solid.

Provenance & Evidence