Water → (2,2-Difluoro-2-pyridin-2-ylethyl)-oxidoazanium

HRID 2053356Notes

Reaction equation

HRID 2053356 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=1[O-])([F:7])[F:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH2:34]>C1COCC1>[F:6][C:5]([F:7])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:4][NH2:1]=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 221851682-(2-Azido-1,1-difluoroethyl)-1-oxo-1lambda~5~-pyridine

Product 1

HCID 87741409(2,2-Difluoro-2-pyridin-2-ylethyl)-oxidoazaniumYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 2-(2-azido-1,1-difluoro-ethyl)-pyridine N-oxide (example 60a, 2.7 g, 13.5 mmol) in THF (40 mL) was slowly added triphenylphosphine (3.9 g, 14.9 mmol) at 0° C. After stirred for 1 h, water (5 mL) was added. The reaction mixture was stirred at 55° C. for 2 h and at room temperature for 12 h. After removal of solvent, the crude was puried by flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-20% methanol in methylene chloride in 30 min) to give 2,2-difluoro-2-pyridin-2-yl-ethylamine N-oxide (2.2 g, 96%) as a white solid. LC-MS m/e 175 (MH+).

Workup

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at 55° C. for 2 h and at room temperature for 12 h
  3. customAfter removal of solvent
  4. customwas puried by flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-20% methanol in methylene chloride in 30 min)

Sources & evidence

ORD record
ord-7b842d4b5e244bca9929237e3472e0bd
Source dataset
uspto-grants-2008_02
Patent number
US07326786B2

Reaction notes

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