Citric Acid → HCID 58508619, compound

Participants

Reaction Steps

Tripotassium phosphate (0.12 g), 1-(tert-butoxycarbonyl)-1H-pyrrole-2-boronic acid (56 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1 mg), and palladium(II) acetate (1 mg) were added to a toluene (3.0 mL) solution of tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.10 g), followed by heating to reflux under a nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, and tripotassium phosphate (47 mg), 1-(tert-butoxycarbonyl)-1H-pyrrole-2-boronic acid (47 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1 mg), and palladium(II) acetate (1 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and ethyl acetate and a 10% aqueous solution of citric acid were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Dioxane (1.5 mL), methanol (1.5 mL), and a 2 mol/L aqueous solution of sodium hydroxide (0.29 mL) were sequentially added to the obtained residue, followed by stiffing at 50° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were sequentially added thereto. The solid substance was collected by filtration to obtain 39 mg of 2-(5-phenylpyridine-3-carboxamido)-4-(1H-pyrrol-2-yl)benzoic acid as a white solid.

Provenance & Evidence