Ethyl Acetate → tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Participants

Reaction Steps

1-(Chloromethyl)-4-methoxybenzene (1 mL, 7.36 mmol) was slowly added to a stirring mixture of tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (3.1 g, 6.134 mmol) and K2CO3 (1.27 g, 9.2 mmol) in DMF (30 mL) at room temperature. After 2 hours, EtOAc (200 mL) and water (100 mL) were added to the mixture, and the phases were separated with warming. The resulting organic suspension was washed with water (3×50 mL) with warming. Final organic phase was concentrated in vacuo without drying over MgSO4 to prevent the loss of the product. The residue was triturated with CH3CN, and the solid formed was filtered, washed with CH3CN (2×10 mL) and dried under high vacuum to provide tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (2.65 g, 69% yield) as a solid. LCMS (APCI+) m/z 626.1 (M+H)+, Retention time=4.96 minutes.

Provenance & Evidence