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

HRID 1519016Notes

Reaction equation

HRID 1519016 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

An amount of 53 mg (0.33 mmol) of 2-chloro-5-chloromethylpyridine dissolved in 6 mL of anhydrous acetonitrile was added to 68 mg (0.33 mmol) of 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide synthesized by the above method, following which 50 mg (0.36 mmol) of potassium carbonate was added and refluxing under heating was carried out for 1 hour. Following reaction completion, the reaction mixture was returned to room temperature then concentrated under reduced pressure. Diethyl ether was added to the concentrate, whereupon a solid separated out. The solid was collected by filtration and dried, affording the target compound in an amount of 49 mg (yield, 45%).

Workup

  1. customsynthesized by the above method
  2. additionwas added
  3. temperaturerefluxing
  4. temperatureunder heating
  5. customreaction completion
  6. customwas returned to room temperature
  7. concentrationthen concentrated under reduced pressure
  8. additionDiethyl ether was added to the concentrate, whereupon a solid
  9. customseparated out
  10. filtrationThe solid was collected by filtration
  11. customdried
  12. customaffording the target compound
  13. customin an amount of 49 mg (yield, 45%)

Sources & evidence

ORD record
ord-f91efe90642c4c8daa5ad8ef51964881
Source dataset
uspto-grants-2015_07
Patent number
US09073866B2

Reaction notes

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