3-Nitrophenylboronic Acid → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(3'-nitro-1,1'-biphenyl-4-yl)acetamide Hydrochloride

Participants

Reaction Conditions

Reaction Steps

61.3 mg (0.37 mmol) of 3-nitrophenylboronic acid, 0.5 ml (1.0 mmol) of 2M aqueous sodium carbonate solution and 12.2 mg (0.02 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride are added to a solution of 120 mg (0.33 mmol) of 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide hydrochloride in 2 ml of DMF. The reaction mixture is stirred at 80° C. for 14 h, cooled, filtered through kieselguhr and then purified by preparative HPLC. The product fractions are concentrated, taken up in a 5:1 mixture of methanol and 1M hydrochloric acid and again concentrated. Drying under high vacuum results in 13 mg (9.7% of theory) of the title compound.

Provenance & Evidence