Potassium Cyanide → HCID 15434618, compound

Participants

Reaction Steps

A mixture of 5-(4-fluorobenzoyl)-6-trifluoromethyl-sulfonyloxy-2-naphthalenesulfonamide (1.0 g, 2.1 mmol) [prepared as described in step 2 above,], potassium cyanide (0.15 mg, 2.3 mmol), and tetrakis(triphenylphosphine)palladium(0) in dioxane (15 ml) was heated at reflux under argon. After 2 h, the reaction mixture was cooled to RT, poured into brine, and the product was extracted into ethyl acetate. The organic layer was dried with sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution, 20-50% ethyl acetate /hexane) and then recrystallized from ethyl acetate-hexane to give 0.44 g of 5-(4-fluorobenzoyl)-6-cyano-2-naphthalenesulfonamide as a white solid (54% yield).

Provenance & Evidence