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INTERMEDIATE 8 4-(3 -Iodo- lH-p yrazol- 1 - vPbenzonitrile To 3-iodo-lH-pyrazole (801 mg, 4.13 mmol) in DMSO (10 mL) at 0 C, was added sodium hydride (60% in mineral oil, 198 mg, 4.95 mmol). The reaction was warmed to 25 C and stirred for 60 min before methyl 4-fluorobenzonitrile (500 mg, 4.13 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combifiash, 0-30% EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l-yl)benzonitrile, as a pale yellow crystaline solid. LCMS calc. = 295.96; found = 295.90 (M+H)+. NMR (500 MHz, CDC13): delta 7.83 (m, 3 H); 7.78 (d, J= 8.5 Hz, 2 H), 6.71 (d, J= 2.6 Hz, 1 H).
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