Dimethylformamide → 2-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

Participants

Reaction Steps

To a solution of 1-methyl-4-phenyl-5-[4-pyridinyl]imidazole (0.275 g, 1.17 mmol) in THF at −78° C. was added n-butyllithium (0.56 mL of 2.5 M solution, 1.40 mmol). The resulting red-orange solution was allowed to stir at −78° C. for 0.5 h when DMF (0.18 mL, 2.34 mmol) was added. The mixture was allowed to warm to rt and stir for 4 h, then quenched with ice water and partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with 50:1 CH2Cl2/MeOH. The title compound was obtained as a white solid (0.187 g, 61%): mp 167-168° C.

Provenance & Evidence