반응 #68971

반응 방정식

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

5-aminopyrazine-2-carbonitrile

cesium carbonate

Xantphos

→

title compound

수율 45.4%

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

수율 45.4%

용매

dioxane

반응 조건

후처리

1. 1
   기타was degassed
2. 2
   기타by bubbling argon through the mixture for 10 minutes
3. 3
   기타The sealed reaction vessel
4. 4
   여과The crude mixture was filtered through an SCX-2 acidic resin cartridge
5. 5
   세척eluting with 2 M ammonia in methanol
6. 6
   농축The basic filtrate was concentrated
7. 7
   기타purified by column chromatography

실험 절차

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).

출처