Ethanol → (1H-Pyrazolo[3,4-b]pyridin-4-yl)methanamine

HRID 888128Notes

Reaction equation

HRID 888128 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]#[N:11])[C:4]=2[CH:3]=[N:2]1.CCO>[NH4+].[OH-].[Ni]>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([CH2:10][NH2:11])=[C:4]2[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 702EthanolHCID 694345511H-pyrazolo[3,4-b]pyridine-4-carbonitrile

Product 1

HCID 55285368(1H-Pyrazolo[3,4-b]pyridin-4-yl)methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

1H-Pyrazolo[3,4-b]pyridine-4-carbonitrile (290 mg, 2.01 mmol) was dissolved in aqueous NH4OH (4 mL) and EtOH (4 mL) then added wet Raney Nickel (2 mL). The reaction was put under a balloon of H2 gas and stirred for 18 h. The mixture was filtered through a pad of Celite®, washing with MeOH. The filtrate was concentrated in vacuo to yield C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine as a tan solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washwashing with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cbc5ed4b438a40d1bac1dcfb425c386b
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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