Azide → 2,2-Difluoro-2-pyridin-2-ylethaneamine

HRID 397473Notes

Reaction equation

HRID 397473 reaction equation
[F:1][C:2]([F:13])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH2:3][N:4]=[N+]=[N-].[N-]=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[F:13][C:2]([F:1])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH2:3][NH2:4]

Participants

5

Reactant 2

HCID 33558AzideHCID 118054052,2-Difluoro-2-(2-pyridyl)ethylazide

Product 1

HCID 99641672,2-Difluoro-2-pyridin-2-ylethaneamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 100 mg of 2,2-difluoro-2-(2-pyridyl)ethylazide I-1-6 was hydrogenated in 10 mL of ethyl acetate over 100 mg of 10% palladium on carbon using a balloon for 1 h. The catalyst was removed by filtration and the solvents removed at reduced pressure. A total of 1.8 g (9.7 mmol) of the azide was reduced using this procedure to give I-1-6 as a yellow oil: 1H NMR (CDCl3) δ8.66 (d, 1H, 4.2 Hz), 7.82 (td, 1H, 7.7, 1.7 Hz), 7.68 (d, 1H, 8.1 Hz), 7.37-7.40 (m, 1H), 3.44 (t, 2H, 14.3 Hz), 1.41 (br s, 2H).

Workup

  1. customfor 1 h
  2. customThe catalyst was removed by filtration
  3. customthe solvents removed at reduced pressure
  4. customto give I-1-6 as a yellow oil

Sources & evidence

ORD record
ord-39b7ec14b3394f1eb0e28168f5443c23
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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