Imidazole → HCID 59633930, compound

HRID 1615087Notes

Reaction equation

HRID 1615087 reaction equation
[F:1][C:2]([F:11])([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18].O>CN(C=O)C>[Si:21]([O:4][CH2:3][C:2]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)([F:1])[F:11])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 59633907β,β-Difluoro-4-pyridineethanol2×

Product 1

HCID 59633930HCID 59633930, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2-difluoro-2-(pyridin-4-yl)-ethanol (0.15 g) prepared in (2) in DMF (3.0 mL) were added imidazole (0.076 g) and tert-butyldimethylchlorosilane (0.15 g). The reaction mixture was stirred at RT for 2 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: ethyl acetate) to give the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (Developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-5147dbfe2e2b4c199ae7c0790d789346
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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