2-(2-Azido-1,1-difluoro-ethyl)-5-methyl-pyridine → 2-Pyridineethanamine, beta,beta-difluoro-5-methyl-

HRID 1987049Notes

Reaction equation

HRID 1987049 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1)([F:7])[F:6])=[N+]=[N-]>CCOC(C)=O.[Pd]>[F:7][C:5]([F:6])([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1)[CH2:4][NH2:1]

Participants

4

Reactant 1

HCID 577227242-(2-Azido-1,1-difluoro-ethyl)-5-methyl-pyridine

Product 1

HCID 577227152-Pyridineethanamine, beta,beta-difluoro-5-methyl-Yield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-Azido-1,1-difluoro-ethyl)-5-methyl-pyridine (2.46 g, 12.42 mol), as prepared in the previous step, in EtOAc (150 mL) was treated with 2.46 g, 10 wt. % Pd—C under a H2 atmosphere. After 24 h, the reaction was filtered through Celite and the filtrate concentrated to afford the product as a clear yellow oil (1.85 g, 10.76 mmol, 86% crude yield). 1H NMR (300 Hz, CDCl3) δ 8.48 (s, 1H), 7.61 (m, 2H), 3.42 (t, J=14.2 Hz), 2.39 (s, 3H); LC/MS (m/z) [M+1]+ 173.0 (calculated for C8H11F2N2, 173.2).

Workup

  1. filtrationthe reaction was filtered through Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-50152bd0c64d4214847c3e040722ec2a
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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