4-Methyloxybenzyl chloride → 7-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine

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Reaction Steps

To 7-iodo-1H-pyrazolo[4,3-b]pyridine (500 mg, 2.041 mmol) in DMF (10 mL) at 0° C. was added 1-(chloromethyl)-4-methoxybenzene (0.292 mL, 2.143 mmol) and the reaction was allowed to warm to room temperature over 1 hour. The reaction mixture was then quenched with saturated ammonium chloride solution and extracted with ethyl acetate (50 mL×2). The organic layers were dried over sodium sulfate and concentrated to give a residue which was loaded onto silica and purified using a 0-77% gradient of ethyl acetate in hexanes 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 immediately. MS [M+H] found 366.2.

Provenance & Evidence