Water → HCID 44223751, compound

HRID 1943957Notes

Reaction equation

HRID 1943957 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:14]([O:15][CH2:16][CH2:17][OH:18])=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)([O-])=O.O>C(O)C.[Fe]>[NH2:3][C:6]1[CH:7]=[C:8]2[C:14]([O:15][CH2:16][CH2:17][OH:18])=[N:13][NH:12][C:9]2=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67053911HCID 67053911, compound

Product 1

HCID 44223751HCID 44223751, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated
  3. customto afford crude product as a solid
  4. customThe crude was absorbed on silica gel
  5. customchromatographed on a silica gel plug with 10:1 ethyl acetate

Sources & evidence

ORD record
ord-ec4b09e5609e44eb8e1410837017dc9f
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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