Potassium Carbonate → 5-Methyl-4-nitro-1-(pyridin-4-yl)methyl-1H-benzimidazole

Participants

Reaction Steps

A 200-mL round-bottomed flask equipped with a magnetic stirrer was charged with 4-picolylchloride hydrochloride (1.20 g, 7.34 mmol) and DMF (30 mL) under argon. A 60% dispersion of sodium hydride in mineral oil (294 mg, 7.34 mmol) was added to the resulting solution and the reaction stirred at room temperature for 5 min. The reaction was then charged with potassium carbonate (3.55 g, 25.7 mmol), stirred at room temperature for 5 min and compound 2b (1.30 g, 7.34 mmol) was added. Once this addition was complete, the reaction was stirred at room temperature for 19 h. After this time the reaction was poured into ethyl acetate (1 L) and the resulting mixture washed with water (3×750 mL) followed by brine (750 mL). The resulting organic layer was dried over sodium sulfate, then filtered and the filtrate concentrated under reduced pressure providing a residue, which was purified by flash chromatography to afford compound 2c as a light-yellow solid.

Provenance & Evidence