Reacción #68971

Ecuación de reacción

tert-butyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

5-aminopyrazine-2-carbonitrile

cesium carbonate

Xantphos

→

title compound

Rendimiento 45.4%

5-(1H-Pyrrolo[2,3-c]pyridin-5-ylamino)pyrazine-2-carbonitrile

Rendimiento 45.4%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas degassed
2. 2
   Otroby bubbling argon through the mixture for 10 minutes
3. 3
   OtroThe sealed reaction vessel
4. 4
   FiltraciónThe crude mixture was filtered through an SCX-2 acidic resin cartridge
5. 5
   Lavadoeluting with 2 M ammonia in methanol
6. 6
   ConcentraciónThe basic filtrate was concentrated
7. 7
   Otropurified by column chromatography

Procedimiento

A mixture of tert-butyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.030 g, 0.119 mmol), 5-aminopyrazine-2-carbonitrile (0.017 g, 0.142 mmol), cesium carbonate (0.077 g, 0.237 mmol), Xantphos (0.011 g, 0.019 mmol) and tris(benzylideneacetone)dipalladium (0) (0.009 g, 0.010 mmol) in dioxane (0.8 mL) was degassed by bubbling argon through the mixture for 10 minutes. The sealed reaction vessel was heated to 150° C. for 1 hour in a microwave reactor. The crude mixture was filtered through an SCX-2 acidic resin cartridge, eluting with 2 M ammonia in methanol. The basic filtrate was concentrated and purified by column chromatography to give the title compound (0.018 g, 0.054 mmol, 45%). LC-MS (3) Rt=1.30 min; m/z (ESI+) 237 (M+H).

Fuente