Sodium Azide → 4-((6-(3-Azido-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxypropyl)pyridin-3-yl)oxy)benzonitrile

HRID 63261Notes

Reaction equation

HRID 63261 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([F:29])([F:28])[C:13]2[N:18]=[CH:17][C:16]([O:19][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH2:11][O:10]1.[N-:30]=[N+:31]=[N-:32].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[N:30]([CH2:11][C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([OH:10])[C:12]([C:13]1[N:18]=[CH:17][C:16]([O:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)=[CH:15][CH:14]=1)([F:29])[F:28])=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 893090844-((6-((2-(2,4-Difluorophenyl)oxiran-2-yl)difluoromethyl)pyridin-3-yl)oxy)benzonitrile

Product 1

HCID 1177204464-((6-(3-Azido-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxypropyl)pyridin-3-yl)oxy)benzonitrileYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-((6-((2-(2,4-difluorophenyl)oxiran-2-yl)difluoromethyl)pyridin-3-yl)oxy)benzonitrile (3.5 g, 8.74 mmol) and sodium azide (1.705 g, 26.2 mmol) in DMF (43.7 mL) was heated at 50° C. for 17 h. The reaction was poured into sat. aq. NaHCO3, and the mixture was extracted with Et2O (3×). The combined organic phases were washed with brine, dried (MgSO4) and concentrated to give the title compound as a brown oil (3.353 g, 69%).

Workup

  1. extractionthe mixture was extracted with Et2O (3×)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9e8e3bc9e9bd4bb4b010383f5613fe20
Source dataset
uspto-grants-2016_09
Patent number
US09447073B2

Reaction notes

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