Trifluoroacetic acid → 2,6-difluoro-3-(4-methyl-1H-imidazol-1-yl)pyridine

HRID 546782Notes

Reaction equation

HRID 546782 reaction equation
FC(F)(F)C(O)=O.C([O-])(=O)C.[NH4+:12].[F:13][C:14]1[C:19]([N:20]([CH2:23][C:24](=O)[CH3:25])[CH:21]=O)=[CH:18][CH:17]=[C:16]([F:27])[N:15]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:13][C:14]1[C:19]([N:20]2[CH:23]=[C:24]([CH3:25])[N:12]=[CH:21]2)=[CH:18][CH:17]=[C:16]([F:27])[N:15]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 86628516N-(2,6-difluoropyridin-3-yl)-N-(2-oxopropyl)formamide

Product 1

HCID 668397352,6-difluoro-3-(4-methyl-1H-imidazol-1-yl)pyridineYield 95.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (1.08 ml) and ammonium acetate (1.08 g) were added to a solution of N-(2,6-difluoropyridin-3-yl)-N-(2-oxopropyl)formamide (2.52 g) in toluene (40 ml), and the reaction solution was heated under reflux in a nitrogen atmosphere for four hours. After leaving to cool, ethyl acetate and a saturated sodium bicarbonate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.19 g). The property values of the compound are as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux in a nitrogen atmosphere for four hours
  3. customAfter leaving
  4. temperatureto cool
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe drying agent was separated by filtration
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c74ed5c829ef47709cb191036fe22a12
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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