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

Participants

Reaction Conditions

Reaction Steps

7-Iodo-1H-pyrazolo[4,3-b]pyridine (0.75 g, 3.06 mmol) and sodium hydride were combined in DMF (30.6 mL) (0.147 g, 3.67 mmol) and stirred for 10 minutes then cooled to 0° C. 1-(Chloromethyl)-4-methoxybenzene (0.438 ml, 3.21 mmol) was added and the reaction was stirred at 0° C. for 15 minutes and then warmed to room temperature over 2 hours. Ice water (200 mL) and saturated ammonium chloride solution (50 mL) was added and the mixture was extracted with ethyl acetate (75 mL×2). The organics were combined, dried over sodium sulfate, and concentrated to dark oil. The oil was dissolved in a mixture of ethyl acetate, methanol and dichloromethane and loaded onto a silica chromatography column which was eluted using 40% 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 as a dark yellow film (1 g) which was used immediately. MS [M+H] found 366.2.

Provenance & Evidence