Furan-3-boronic acid → N-[1-(3-chloro-5-furan-3-yl-pyridin-2-yl)-cyclopropylmethyl]-2,6-difluoro-benzamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-furylboronic acid (80 μmol) in toluene (0.3 ml) was added successively a solution of N-[1-(5-bromo-3-chloro-pyridin-2-yl)-cyclopropylmethyl]-2,6-difluorobenzamide (40 μmol) (from step 4) in toluene (0.5 ml), aqueous sodium carbonate 2M (0.06 ml), water (0.4 ml) and a solution of tetrakis(triphenylphosphine)palladium (4 μmol) in toluene (0.2 ml). The reaction mixture was stirred at 90° C. for 16 hours under an atmosphere of Argon. The reaction mixture was evaporated. The crude mixture was extracted 3 times with ethyl acetate and water. The organic phases were combined and evaporated. The crude product was dissolved in N,N-dimethylformamide (1ml) and purified by HPLC to give 2.45 mg N-[1-(3-chloro-5-furan-3-yl-pyridin-2-yl)-cyclopropylmethyl]-2,6-difluoro-benzamide.

Provenance & Evidence