Benzo(B)Thiophene-2-Boronic Acid → HCID 57879571, compound

Participants

Reaction Conditions

Reaction Steps

56 mg of benzothiophene-2-boronic acid, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) 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 12 hours. After cooled to room temperature 37 mg of benzothiophene-2-boronic acid and 22 mg of sodium carbonate were added and stirred at 90° C. for 12 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.0 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 and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 2.0 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 to the reaction mixture and a solid substance was separated by filtration to obtain 2.5 mg of 2-(benzamido)-4-(benzothiophen-2-yl)benzoic acid as white solid.

Provenance & Evidence