Sodium Carbonate → HCID 68963377, compound

Participants

Reaction Conditions

Reaction Steps

To N,N-dimethylacetamide 2.5 mL solution of methyl 4-bromo-2-(4-fluoroanilino)benzoate 70 mg were added 4-(acetamido)phenylboronic acid 77 mg, sodium carbonate 69 mg and polymer-carried di(acetato)dicyclohexylphenylphosphine palladium(II) 31 mg, and it was stirred at 90° C. for 12 hours. After the reaction mixture was cooled to room temperature, 4-(acetamido)phenylboronic acid 39 mg and sodium carbonate 22 mg were added, and it was stirred at 95° C. for 14 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Ethanol 2.0 mL and 2.0 mol/L sodium hydroxide aqueous solution 1.0 mL were added to the obtained residue, and it was stirred at room temperature for 1 hour. 6.0 mol/L hydrochloric acid 0.50 mL, water 3.0 mL and ethyl acetate 4.0 mL were added to the reaction mixture. The organic layer was separated and collected, and the solvent was removed under reduced pressure. The obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 40-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 4-(4-(acetamido)phenyl)-2-(4-fluoroanilino)benzoic acid 14 mg of a pale yellow solid.

Provenance & Evidence