Sodium Carbonate → 4-(4-(Acetamido)phenyl)-2-(benzamido)benzoic acid

Participants

Reaction Conditions

Reaction Steps

56 mg of 4-(acetamido)phenylboronic acid, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(11) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of methyl 2-(benzamido)-4-bromobenzoate, and stirred at 90° C. for 11 hours. After the reaction mixture was cooled to room temperature, 19 mg of 4-(acetamido)phenylboronic acid was added and the mixture was stirred at 90° C. for 12 hours. After the reaction mixture was cooled to room temperature, 11 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added and stirred at 90° C. for 14 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.2 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 1 mL of 1.0 mol/L aqueous sodium hydroxide and 2 mL of ethanol were added to the obtained residue and stirred at room temperature for 1 hour. 0.6 mol/L hydrochloric acid was added, and solid substances were separated by filtration and purified with reversed-phase silica gel column chromatography [eluent; 40-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to obtain 5.9 mg of 4-(4-(acetamido)phenyl)-2-(benzamido)benzoic acid as white solid.

Provenance & Evidence