Potassium Carbonate → 2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide

HRID 623294Notes

Reaction equation

HRID 623294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[Cl:10][C:11]([F:22])([F:21])[C:12]([N:14]=[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][NH:16]1)=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:10][C:11]([F:21])([F:22])[C:12]([N:14]=[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]1[CH2:8][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 178522124HCID 178522124, compound

Product 1

HCID 866869322-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

53 mg (0.33 mmol) of 2-chloro-5-chloromethyl pyridine dissolved in 6 ml of anhydrous acetonitrile was added to 68 mg (0.33 mmol) of the 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide synthesized by the aforementioned method, and subsequently, 50 mg (0.36 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 1 hours. After the reaction was completed, the reaction solution was returned to room temperature and then concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 49 mg (yield 45%).

Workup

  1. customsynthesized by the aforementioned method
  2. temperaturethe resulting mixture was heated
  3. temperaturerefluxed for 1 hours
  4. customwas returned to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionDiethyl ether was added
  7. customto precipitate a solid
  8. customthus the solid was collected
  9. customdried
  10. customto obtain the subject material
  11. customAmount obtained 49 mg (yield 45%)

Sources & evidence

ORD record
ord-03c4d64fd69f4a72b3916c9c53297123
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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