Reaction #710473

Reaction equation

difluoroacetic acid

EDC-HCl

2-aminopyridine

→

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

Yield 14.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Washwashed once with water and twice with a 1% HCl aqueous solution
2. 2
   Dryingdried over anhydrous magnesium sulfate
3. 3
   Concentrationconcentrated under reduced pressure

Procedure

400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml of anhydrous dichloromethane, 322 μl (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of EDC-HCl and 622 mg (5.11 mmol) of DMAP were added thereto, and the resulting mixture was stirred at room temperature for 61 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 102 mg (yield 14%) of 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.

Source