(c)(d) N′-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methylene)-4-methylbenzenesulfonohydrazide (1.82 g, 3.77 mmol) was dissolved in 20 mL of dioxane and 20 mL of a 50% aqueous NaOH solution and heated at 85 C. After 1 h, the reaction mixture was adjusted to pH 4-5 with conc HCl and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated, and the crude product was taken to the next step. Crude residue was dissolved in 20 mL of benzene and acrylonitrile (4 mmol) was added. The reaction mixture was heated to reflux. After 2 h, the reaction was poured into brine and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated, and then purified by HPLC to give 275 mg (21% yield) of 2-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylcyclopropanecarbonitrile. MS found: (M+H)+=354.
