Reaction #531879

Reaction equation

ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate

2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine hydrochloride

triethylamine

→

ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate

Yield 100.3%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherthe mixture was evaporated
2. 2
   workup.ADDITIONThe residue was diluted with AcOEt
3. 3
   Filtrationthe precipitate was filtered off
4. 4
   OtherThe filtrate was evaporated

Procedure

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.1 g, 0.369 mmol, 1 eq.) in 5 ml of tetrahydrofuran were added 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine hydrochloride (0.106 g, 0.40 mmol, 1.1 eq.) and triethylamine (TEA) (0.112 g, 1.10 mmol, 3 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate (0.170 g, 99% yield).

Source