Sodium hydride → 1-(4-methanesulfonyl-benzyl)-3-nitro-1H-pyrazole

Participants

Reaction Steps

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 150 mg, 1.33 mmol) in anhydrous N,N-dimethylformamide (2 mL), a 60% dispersion of sodium hydride in mineral oil (58 mg, 1.46 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 30 min, 1-bromomethyl-4-methanesulfonyl-benzene (364 mg, 1.46 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 1-(4-methanesulfonyl-benzyl)-3-nitro-1H-pyrazole (207 mg, 55%) as a white solid.

Provenance & Evidence