Reacción #58696

Ecuación de reacción

2-chloro-3-cyanopyridine

ethyl 2-mercaptoacetate

sodium carbonate

EtOH

→

title compound

Rendimiento 93.2%

Ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

Rendimiento 93.2%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux for 4.5 hours
3. 3
   workup.ADDITIONthe addition
4. 4
   Lavadowas washed in with water (5 L)
5. 5
   Filtraciónit was filtered
6. 6
   LavadoThe filter cake was washed with two portions of water (2×2.5 L)
7. 7
   Otrodried at the pump
8. 8
   OtroThe solids were then dried to constant weight under vacuum at 45° C.

Procedimiento

A mixture of 2-chloro-3-cyanopyridine (330 g), ethyl 2-mercaptoacetate (361.2 g), sodium carbonate (265 g) and EtOH (1.2L) was heated to reflux for 4.5 hours. It was then cooled to ambient temperature, added to water (10 L) and the addition was washed in with water (5 L). The resulting slurry was stirred for 30 minutes and then it was filtered. The filter cake was washed with two portions of water (2×2.5 L) and dried at the pump. The solids were then dried to constant weight under vacuum at 45° C. to yield the title compound as a brown solid (493.1 g, 93.2%). δH (CDCl3) 8.68 (1H, dd, J 4.7, 1.2 Hz), 7.93 (1H, dd, J 8.5, 1.2 Hz), 7.29 (1H, dd, J 8.5, 4.7 Hz), 5.90 (2H, b), 4.38 (2H, q, J 7.0 Hz), 1.40 (3H, t, J 7.0 Hz). LCMS RT 2.9 minutes, 223 (M+H)+

Fuente