Tert-Butyl nitrite → HCID 67111062, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-[3-(2-amino-4-fluorophenoxy)-1-ethyl-1H-pyrazol-5-yl]benzonitrile (262 mg, 0.813 mmol, 1 equiv) in N,N-dimethylformamide (2 mL) was added dropwise over 5 minutes to a solution of t-butylnitrite (0.15 mL, 1.2 mmol, 1.5 equiv) in N,N-dimethylformamide (2.5 mL) at 60° C. The reaction mixture was stirred at 60° C. for 20 minutes, then was partitioned between ethyl acetate and aqueous hydrochloric acid solution (1 M). The organic layer was washed sequentially with an additional portion of aqueous hydrochloric acid solution (1 M) and saturated aqueous sodium chloride solution. The washed organic layer was dried over sodium sulfate, and the dried solution was filtered. The filtrate was concentrated, and the residue was purified by flash-column chromatography on silica gel (hexanes, grading to 50% ethyl acetate-hexanes) to afford 3-[1-ethyl-3-(4-fluorophenoxy)-1H-pyrazol-5-yl]benzonitrile (127 mg, 51%) as a white solid. Calcd (M+1)+: 308.1. Found: 308.0.

Provenance & Evidence