5-Nitro-2-phenyl-2H-pyrazolo [3,4-b]pyridine → 2-Phenyl-2H-pyrazolo[3,4-b]pyridin-5-amine

HRID 901215Notes

Reaction equation

HRID 901215 reaction equation
[N+:1]([C:4]1[CH:9]=[N:8][C:7]2=[N:10][N:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:6]2[CH:5]=1)([O-])=O>CCOC(C)=O.CO.[Pd]>[C:13]1([N:11]2[CH:12]=[C:6]3[C:7]([N:8]=[CH:9][C:4]([NH2:1])=[CH:5]3)=[N:10]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 1

HCID 586701485-Nitro-2-phenyl-2H-pyrazolo [3,4-b]pyridine

Product 1

HCID 586701512-Phenyl-2H-pyrazolo[3,4-b]pyridin-5-amineYield 99.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3B (350 mg, 1.458 mmol) and palladium (5% wt) on activated carbon (300 mg) in EtOAc(100 mL) and MeOH (200 mL) was stirred under a hydrogen balloon for 1 hour. The reaction mixture was filtered via a pad of Celite. The filtrate was concentrated under reduced pressure to give the title compound as a light brown solid (305 mg, 99% yield). LC/MS (method A): retention time=1.60 min, (M+H)+=211.

Workup

  1. filtrationThe reaction mixture was filtered via a pad of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0d5d8cda4be84c84a81ffc55e7ddf9cc
Source dataset
uspto-grants-2008_04
Patent number
US07361766B2

Reaction notes

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