Dimethylcarbamoyl Chloride → HCID 23154955, compound

Participants

Reaction Conditions

Reaction Steps

In a mixed solvent of 1 mL of dimethylformamide and 2 mL of dioxane, 100 mg (0.39 mmol) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine 5-oxide prepared in Step A of Example 90 was dissolved, and 310 μL (0.78 mmol) of tri-methylsilylcyanide and 144 μL (0.78 mmol) of N,N-dimethylcarbamoyl chloride were added thereto and the mixture solution was stirred at 90° C. for 14 hours. The solvent was distilled, and the residue was partitioned between ethyl acetate (10 mL×2) and a sodium hydrogencarbonate aqueous solution (10 mL). The combined organic layers was washed with a saturated sodium chloride solution, dried on anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was triturated with ethyl acetate to obtain 78 mg (75%) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile as a pale yellow solid.

Provenance & Evidence