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0 °C

7-Iodo-1H-pyrazolo[4,3-b]pyridine (500 mg, 2.041 mmol) and NaH (103 mg, 60% in oil, 4.08 mmol) were combined in DMF (10 mL) at 25° C. After 10 minutes, the mixture was cooled to 0° C. and 1-(chloromethyl)-4-methoxybenzene (0.297 mL, 2.143 mmol) was added and the mixture stirred for a further 15 minutes. The ice bath was removed and the mixture stirred for 1 hour then diluted with water (150 mL) and saturated ammonium chloride solution (50 mL). The product was extracted into EtOAc. The organic layers were combined, dried over magnesium sulfate, filtered and evaporated in vacuo onto silica and subjected to chromatography on silica eluted with EtOAc in hexanes (0-50%) to give 7-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine and 7-iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine which was used without further purification.

1. customThe ice bath was removed
2. stirringthe mixture stirred for 1 hour
3. additionthen diluted with water (150 mL) and saturated ammonium chloride solution (50 mL)
4. extractionThe product was extracted into EtOAc
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporated in vacuo onto silica
8. washeluted with EtOAc in hexanes (0-50%)