Methyl 4-(bromomethyl)benzoate → HCID 18963773, compound

Participants

Reaction Steps

Methyl 4-(bromomethyl)benzoate (479 mg, 2.09 mmol) is added to a room temperature solution of 3-mercapto-5-methoxybenzo[b]thiophene-2-carboxamide (200 mg, 0.84 mmol) in 12 mL of THF followed by NaHCO3 (351 mg, 4.18 mmol) and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, saturated NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:dichloromethane (1:9 to 1:1) followed by recrystallization from ethyl acetate:hexane provides methyl 4-[[[2-(aminocarbonyl)-5-methoxybenzo[b]thien-3-yl]thio]methyl]-benzoate in 68% yield; mp=150°-152° C.

Provenance & Evidence