Diisopropylethylamine → 3-[(4-Chlorophenyl)(3-{2-fluoro-1-[3-fluoro-5-(4H-1,2,4-triazol-4-yl)phenyl]-2-methylpropyl}azetidin-1-yl)methyl]benzonitrile

Participants

Reaction Steps

A sample of 135 mg (0.41 mmole) of 4-[3-(1-Azetidin-3-yl-2-fluoro-2-methylpropyl)-5-fluorophenyl]-4H-1,2,4-triazole hydrochloride, 211 mg (0.62 mmole) of 3-[bromo(4-chlorophenyl)methyl]benzonitrile and 181 uL (1.025 mmole) of diisopropylethylamine in 5 mL of dry CH3CN was heated at reflux for 3 h. The solution was concentrated and the residue was dissolved in 20 mL of CH2Cl2 and 5 mL of NaHCO3. The layers were separated and the organic phase was dried over Na2SO4 and concentrated. The residue was purified on silica gel using CH2Cl2-EtOAc—NH3 (2M in MeOH), 200:50:4 to afford the title compound as a mixture of 4 diastereomers: Mass Spectrum: m/e=518 (M+1).

Provenance & Evidence