2,2-Difluoro-2-(2-pyridyl)ethylazide → 2,2-Difluoro-2-pyridin-2-ylethaneamine

HRID 990710Notes

Reaction equation

HRID 990710 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-].[H][H]>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 118054052,2-Difluoro-2-(2-pyridyl)ethylazideHCID 178418361HCID 178418361, compound

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)ethyl azide was hydrogenated in 10 ml of ethyl acetate over 100 mg of 10% palladium on carbon under a balloon of hydrogen for 1 h. The catalyst was removed by filtration and the solvents removed at reduced pressure to give 1-10 as a yellow oil: 1H NMR (CDCl3) δ6 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, 2 H, 14.3 Hz), 1.41 (br s, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents removed at reduced pressure

Sources & evidence

ORD record
ord-25d8da2f03964a9eaf46876872ca353d
Source dataset
uspto-grants-2002_10
Patent number
US06462050B1

Reaction notes

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