Ammonium Chloride → HCID 178424086, compound

Participants

Reaction Conditions

Reaction Steps

N-(5′-cyano-2′-methyl-biphenyl-4-yl)-2,6-difluoro-benzamide (Compound A) was prepared by an analogous method as Compound 1 except that 3-bromo-4-methyl-benzoic acid methyl ester was replaced with 2-bromo-4-cyano-toluene. A mixture of Compound A (348 mg 1 mmol), sodium azide (78 mg 1.2 mmol), and ammonium chloride (65 mg, 1.2 mmol) in DMF (5 ml) was stirred and heated at 120° C. for 10 hr. After cooling the reaction mixture to room temperature, EtOAc (200 ml) was added, and the mixture was washed with water (60 ml×3). The EtOAc layer was concentrated and the residue was subjected to silica gel chromatography (Hexanes:EtOAc, EtOAc:MeOH) to give the product, 2,6-difluro-N-[2′-methyl-5′-(1H-tetrazol-5-yl)-biphenyl-4-yl]-benzamide (313 mg, yield 80%) as a off-white solid.

Provenance & Evidence