Sodium Carbonate → Tert-butyl 2-(benzamido)-4-(4-(dimethylamino)phenyl)benzoate

Participants

Reaction Conditions

Reaction Steps

46 mg of 4-(dimethylamino)phenylboronic acid, 49 mg of sodium carbonate and 5.7 mg of polymer supported di(acetato)dicyclohexylphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate, and stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature 5.7 mg polymer supported di(acetato)dicyclohexylphenylphosphine palladium(II) was added and stirred at 110° C. for 24 hours, After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1] to obtain tert-butyl 2-(benzamido)-4-(4-(dimethylamino)phenyl)benzoate.

Provenance & Evidence