3-(azidomethyl)-1H-pyrrolo[2,3-b]pyridine → (1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine

HRID 1890506Notes

Reaction equation

HRID 1890506 reaction equation
[N:1]([CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH:7]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[C:5]([CH2:4][NH2:1])=[CH:6]1

Participants

4

Reactant 1

HCID 866714293-(azidomethyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 17959419(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-(azidomethyl)-1H-pyrrolo[2,3-b]pyridine (A-4) (1.50 g, 8.63 mmol) in EtOAc (150 mL) was added 10% Pd/C (1.10 g). The resulting reaction mixture was stirred under one atmosphere of H2 at room temperature for 3 h. The mixture was filtered, and the filtrate was concentrated to afford the title compound (1.15 g).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3a59566f97ec49559bc8d225a354f851
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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