Ammonium Chloride → HCID 68762104, compound

Participants

Reaction Conditions

Reaction Steps

Methylzinc (II) chloride (2M solution in THF, 1244 μL, 2.488 mmol) was added to a solution of tert-butyl 4-(5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (500 mg, 0.995 mmol) and Pd(PPh3)4 (86.25 mg, 0.07464 mmol) in THF (5 mL) under a nitrogen atmosphere. The reaction mixture was stirred at 75° C. for 1.5 hours and allowed to cool to room temperature. The mixture was poured into a saturated aqueous NH4Cl solution (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel (Biotage Flash 40S+) eluting with 2% MeOH/CH2Cl2 to provide tert-butyl 4-(1-(4-methoxybenzyl)-5-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (470 mg, 0.806 mmol, 81.0% yield) as a solid. LCMS (APCI+) m/z 438.2 (M+H)+.

Provenance & Evidence