Methyl 5-bromovalerate → HCID 18963778, compound

Participants

Reaction Steps

Methyl 5-bromovalerate (144 μL, 1.00 mmol) is added to a room temperature solution of 3-mercapto-5-methoxybenzo[b]thiophene-2-carboxamide (200 mg, 0.84 mmol) in 8 mL of THF followed by NaHCO3 (351 mg, 4.18 mmol) and the reaction mixture is stirred at room temperature overnight. Additional methyl 5-bromovalerate (100 μL) is added and the reaction mixture is stirred at room temperature for 3 days. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, water, saturated NaHCO3, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives methyl 3-[[2-(aminocarbonyl)-5-methoxybenzo[b]thien-3-yl]thio]pentanoate in 30% yield; mp=134.5°-135.5° C.

Provenance & Evidence