Water → HCID 44223751, compound

Participants

Reaction Conditions

Reaction Steps

Iron powder (0.075 g 1.34 mmol) and ammonium chloride (0.14 g, 2.68 mmol) were added to 2-(5-nitro-1H-pyrazolo[3,4-b]pyridin-3-yloxy)ethanol (60 mg, 0.27 mmol) in ethanol:water (5 mL, 2:1). The mixture was heated at 85° C. in a sealed vial. After 5 hours, the reaction mixture was filtered and evaporated to afford crude product as a solid. The crude was absorbed on silica gel and chromatographed on a silica gel plug with 10:1 ethyl acetate:methanol. Fractions 2-5 contained 2-(5-amino-1H-pyrazolo[3,4-b]pyridin-3-yloxy)ethanol (21.8 mg, 0.112 mmol, 42% yield) as a solid.

Provenance & Evidence