Reaktion #68971

Reaktionsgleichung

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

5-aminopyrazine-2-carbonitrile

cesium carbonate

Xantphos

→

title compound

Ausbeute 45.4%

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

Ausbeute 45.4%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed
2. 2
   Sonstigeby bubbling argon through the mixture for 10 minutes
3. 3
   SonstigeThe sealed reaction vessel
4. 4
   FiltrationThe crude mixture was filtered through an SCX-2 acidic resin cartridge
5. 5
   Wascheneluting with 2 M ammonia in methanol
6. 6
   EinengenThe basic filtrate was concentrated
7. 7
   Sonstigepurified by column chromatography

Vorschrift

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).

Quelle