Potassium Iodide → N-(2,6-difluoropyridin-3-yl)-N-(2-oxopropyl)formamide

HRID 546781Notes

Reaction equation

HRID 546781 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[F:14][C:15]1[C:20]([NH:21][CH:22]=[O:23])=[CH:19][CH:18]=[C:17]([F:24])[N:16]=1>CN(C)C=O.O.C(OCC)(=O)C>[F:14][C:15]1[C:20]([N:21]([CH2:2][C:3](=[O:5])[CH3:4])[CH:22]=[O:23])=[CH:19][CH:18]=[C:17]([F:24])[N:16]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 86628515N-(2,6-difluoropyridin-3-yl)formamide

Product 1

HCID 86628516N-(2,6-difluoropyridin-3-yl)-N-(2-oxopropyl)formamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetone (1.83 ml), cesium carbonate (7.99 g) and potassium iodide (254 mg) were added to a solution of N-(2,6-difluoropyridin-3-yl)formamide (2.42 g) in N,N-dimethylformamide (50 ml), and the reaction solution was stirred at room temperature for two hours. Ethyl acetate and water 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 (2.52 g). The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe drying agent was separated by filtration
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cfc561bdf5c74c69baf3294907009449
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…