Dimethylformamide → 5-(2-Chloro-pyridin-4-ylethynyl)-3-(4-fluoro-phenyl)-2-methyl-3H-imidazole-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

2-chloro-4-[1-(4-fluoro-phenyl)-2-methyl-1H-imidazol-4-ylethynyl]-pyridine (2.0 g, 6.42 mmol) was dissolved in 50 mL THF and cooled to −70° C. Lithiumdiisopropylamide 2M/THF (4.8 ml, 9.6 mmol) was added, and the mixture stirred for 15 min at −70° C. Dimethylformamide (0.69 ml, 9.0 mmol) was added and stirring was continued at −70° C. for 3 hrs. The reaction mixture was quenched with sat. NaHCO3− solution and extracted with water and ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethylacetate 1:2). The desired compound was obtained as a yellow solid (220 mg, 10%), MS: m/e=340.0 (M+H+).

Provenance & Evidence