Reaction #710480

Reaction equation

ethyl acetate

5-bromomethyl-2-fluoropyridine

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

potassium carbonate

→

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

Yield 26.0%

Solvents

water

DMF

DMF

Conditions

Workup

1. 1
   workup.ADDITIONadded
2. 2
   Otherwas returned to room temperature
3. 3
   Otherliquid separation
4. 4
   WashThe organic layer was washed with 1% hydrochloric acid
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   workup.ADDITIONA small amount of hexane and diethyl ether were added
8. 8
   Otherto precipitate crystals
9. 9
   Otherthus the crystals were collected
10. 10
    Otherdried
11. 11
    Otherto obtain the subject material
12. 12
    OtherAmount obtained 50 mg (yield 26%)

Procedure

128 mg (0.75 mmol) of 5-bromomethyl-2-fluoropyridine was dissolved in 3 ml of anhydrous DMF, 116 mg (0.68 mmol) of 2,2-difluoro-N-[pyridin-2(1H)-ylidene]acetamide was dissolved in 3 ml of anhydrous DMF and added thereto, and subsequently, 103 mg (0.75 mmol) of potassium carbonate was added thereto and the resulting mixture was stirred at 65° C. for 2 hours. After the reaction was completed, the reaction solution was returned to room temperature, and ethyl acetate and water were added thereto to perform liquid separation. The organic layer was washed with 1% hydrochloric acid, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A small amount of hexane and diethyl ether were added thereto to precipitate crystals, and thus the crystals were collected and dried to obtain the subject material. Amount obtained 50 mg (yield 26%).

Source