[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][CH:17]=2)[CH:6]=[C:7](C2C=CC=CC=2)[CH:8]=1.C1C(=O)N([I:25])C(=O)C1.C(OCC)(=O)C.O>C(#N)C>[I:25][C:17]1[CH:16]=[N:15][N:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=124-methoxy-6-phenylpyrazolo[1,5-a]pyridine (17, 200 mg, 0.892 mmol) and NIS (241 mg, 1.070 mmol) were dissolved in acetonitrile (20 mL) and stirred at room temperature for 1 hour. The reaction was then poured into ethyl acetate and water, extracted organics, washed 1N NaOH and brine, dried with magnesium sulfate, filtered, and concentrated to give a white solid. This was purified by column chromatography (0-30% ethyl acetate in hexanes, linear gradient) and to yield 3-iodo-4-methoxypyrazolo[1,5-a]pyridine (18, 310 mg, 0.885 mmol, 99% yield). MS APCI: [M+H]+ m/z 351.2.
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