Water → HCID 58679084, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (4.73 g, 13.8 mmol) and 5-benzyloxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine (5.84 g, 17.9 mmol) produced by the method described in WO2005/080399 in 1,2-dimethoxyethane (50 ml) and water (50 ml) were added sodium hydrogen carbonate (1.72 g, 20.7 mol) and tetrakis(triphenylphosphine)palladium (799 mg, 0.691 mol), and the mixture was stirred overnight with heating at 110° C. The reaction mixture was allowed to cool to room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure and the residue was purified y silica gel column chromatography (hexane:ethyl acetate=3:1) to give methyl 5-(2-amino-4-benzyloxyphenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (5.93 g, yield 93%).

Provenance & Evidence