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

HRID 1795287Notes

Reaction equation

HRID 1795287 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([F:7])[F:6])=[N+]=[N-].[N-]=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[F:7][C:5]([F:6])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:4][NH2:1]

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-azido-1,1-difluoro-ethyl)-pyridine 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 2,2-difluoro-2-pyridin-2-yl-ethylamine as a yellow oil: 1H NMR (CDCl3) δ 8.66 (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

Sources & evidence

ORD record
ord-5d72eee4a22440b28876a3a4d37d7f42
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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