Formic Acid → N-(2,6-difluoropyridin-3-yl)formamide

HRID 546780Notes

Reaction equation

HRID 546780 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[F:11][C:12]1[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([F:19])[N:13]=1.C(=O)(O)[O-].[Na+]>COC(C)(C)C.C(OCC)(=O)C>[F:11][C:12]1[C:17]([NH:18][CH:5]=[O:7])=[CH:16][CH:15]=[C:14]([F:19])[N:13]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 450800062,6-Difluoropyridin-3-amine

Product 1

HCID 86628515N-(2,6-difluoropyridin-3-yl)formamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Acetic anhydride (6 ml) was added to formic acid (6 ml), followed by stirring at room temperature for 20 minutes. Then, a solution of 2,6-difluoro-3-aminopyridine (2.06 g) in tert-butyl methyl ether (7 ml) was added so that the reaction solution was maintained at room temperature. The reaction solution was further stirred at room temperature for four hours. 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 (2.42 g). The property values of the compound are as follows.

Workup

  1. temperaturewas maintained at room temperature
  2. stirringThe reaction solution was further stirred at room temperature for four hours
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-baa37e6433c247bc9d522fbb5ae9a100
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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