Hydrochloric Acid → 3-Bromo-1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-bromo-1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (112 mg, 0.288 mmol) was suspended in THF (0.5 mL) and ethanol (1.5 mL), followed by addition of 3N NaOH (150 μl, 0.433 mmol). The reaction mixture was stirred at 55° C. for 3 hours, and then allowed to cool to room temperature. The reaction mixture was diluted with water (1.5 mL), cooled in an ice bath, and acidified with 1N HCl in a dropwise manner. The mixture was extracted with EtOAc. The organic layer was separated and concentrated in vacuo to afford a solid that dried on the high vacuum 3 hours. The product was collected as a pale yellow solid (93.6 mg, 90%). LCMS E-S (M+H)=360.0/362.2. 1H NMR (400 MHz, MeOD) δ8.22 (dd, J=1.52, 8.08 Hz, 2H), 8.05 (s, 1H), 7.48-7.59 (m, 3H), 5.47 (quip, J=6.76 Hz, 1H), 1.63 (d, J=6.82 Hz, 6H)

Provenance & Evidence