Reaction #710469

Reaction equation

potassium carbonate

5-bromomethyl-2-fluoropyridine

2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide

→

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

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturein sequence, and the resulting mixture was heated
3. 3
   Temperaturerefluxed for 6 hours
4. 4
   Otherwas returned to room temperature
5. 5
   Filtrationto filter insoluble materials
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   OtherThe filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→3:1)
8. 8
   Otherto obtain the subject material
9. 9
   OtherAmount obtained 21 mg (yield 23%)

Procedure

57 mg (0.30 mmol) of the 5-bromomethyl-2-fluoropyridine obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 57 mg (0.30 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide synthesized by the method described in (1) of Synthetic Example P1 and 69 mg (0.50 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→3:1) to obtain the subject material. Amount obtained 21 mg (yield 23%).

Source