Sodium hydride → Pyridine, 2-(4-nitro-1H-imidazol-1-yl)-

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Reaction Conditions

Reaction Steps

A suspension of 4-nitro-1H-imidazole (0.5 g, 4.4 mmol) in DMF (15 ml) was cooled to 0° C. and treated with sodium hydride (0.23 g, 5.3 mmol). Stirring was continued at 0° C. for 1 h and subsequently cooled to −30° C. A solution of N-fluoropyridinium triflate (0.55 g, 2.2 mmol) in DMF (10 ml) was added within 5 min. After warming-up to ambient temperature, the reaction mixture was stirred at that temperature overnight. The crude product was obtained after extraction with ethyl acetate (2×100 ml), washing of the combined organic phases with 10% aqueous potassium bisulphate solution, water and brine and finally drying and solvent evaporation. This off-white solid material (0.33 g, 39%) was used without any further purification for the next step. MS: M=191.3 (M+H)+

Provenance & Evidence