Benzonitrile → Pyridine, 4-[2-(4-methoxyphenyl)-1-methyl-4-phenyl-1H-imidazol-5-yl]-

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.16 mL, 1.1 mmol) in THF at -78° C. was added n-butyllithium (0.38 mL of 2.5 M solution, 0.95 mmol). To the resulting mixture was added a solution of 4-methoxy-N-methyl-N-(4-picolyl)benzamide (0.16 g, 0.62 mmol) in THF. The resulting dark red solution was warmed to -40° C. and stirred for 15 min, at which time benzonitrile (0.13 mL, 1.2 mmol) was added. The mixture to warmed to rt and stirred for 10 h. Aqueous NH4Cl (0.5 mL,) was added, and the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 2-4% MeOH/CHCl3. The material which was isolated was triturated with Et2O and recrystallized from EtOAc to provide the title compound as an off-white solid (35 mg, 17%): nap 193°-194° C.

Provenance & Evidence