Potassium Carbonate → HCID 89613470, compound

HRID 623292Notes

Reaction equation

HRID 623292 reaction equation
[F:1][CH:2]([F:12])[C:3]([N:5]=[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][NH:7]1)=[O:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:13][C:14]1[N:15]=[CH:16][C:17]([CH2:20][N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:3](=[O:4])[CH:2]([F:1])[F:12])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 178522122HCID 178522122, compound

Product 1

HCID 89613470HCID 89613470, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

100 mg (0.58 mmol) of the 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 94 mg (0.58 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 5 ml of anhydrous acetonitrile and added thereto, and subsequently, 84 mg (0.63 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 140 minutes. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Ether was added thereto to precipitate a solid, and thus the solid was collected and dried well to obtain the subject material. Amount obtained 63 mg (yield 37%).

Workup

  1. additionadded
  2. temperaturethe resulting mixture was heated
  3. temperaturerefluxed for 140 minutes
  4. customwas returned to room temperature
  5. filtrationto filter off insoluble materials
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionEther was added
  8. customto precipitate a solid
  9. customthus the solid was collected
  10. customdried well
  11. customto obtain the subject material
  12. customAmount obtained 63 mg (yield 37%)

Sources & evidence

ORD record
ord-33f9a6e2123d479b831d9b3f93761ca6
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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