Reaction #531880

Reaction equation

triethylamine

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

1-(6-chloropyridin-3-yl)ethanamine

→

ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-{[1-(6-chloropyridin-3-yl)ethyl]amino}-2-cyanoacrylate

Yield 73.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe reaction was microwaved
2. 2
   Other(130° C., 600 s, fixed hold, high absorption)
3. 3
   Otherthe solvent evaporated

Procedure

To a solution of ethyl 3-chlor-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.150 g, 0.55 mmol, 1 eq.) in 3 ml of acetonitrile was added 1-(6-chloropyridin-3-yl)ethanamine (0.103 g, 0.66 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.167 g, 1.66 mmol, 3 eq.). The reaction was microwaved (130° C., 600 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-{[1-(6-chloropyridin-3-yl)ethyl]amino}-2-cyanoacrylate (0.157 g, 68% yield) as a mixture of 2 atropoisomers.

Source