Reaction #710474

Reaction equation

2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide

2-chloro-5-chloromethyl pyridine

potassium carbonate

→

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

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONadded
2. 2
   Temperaturethe resulting mixture was heated
3. 3
   Temperaturerefluxed for 140 minutes
4. 4
   Otherwas returned to room temperature
5. 5
   Filtrationto filter off insoluble materials
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   workup.ADDITIONEther was added
8. 8
   Otherto precipitate a solid
9. 9
   Otherthus the solid was collected
10. 10
    Otherdried well
11. 11
    Otherto obtain the subject material
12. 12
    OtherAmount obtained 63 mg (yield 37%)

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%).

Source