Cesium carbonate → 5-(1H-pyrrolo[2,3-c]pyridin-5-ylamino)pyrazine-2-carbonitrile
Reaktionsgleichung
Cl[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8](C(OC(C)(C)C)=O)[C:5]2=[CH:6][N:7]=1.[NH2:18][C:19]1[N:20]=[CH:21][C:22]([C:25]#[N:26])=[N:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1>[NH:8]1[C:5]2=[CH:6][N:7]=[C:2]([NH:18][C:19]3[N:20]=[CH:21][C:22]([C:25]#[N:26])=[N:23][CH:24]=3)[CH:3]=[C:4]2[CH:10]=[CH:9]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
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).
Aufarbeitung
- customwas degassed
- customby bubbling argon through the mixture for 10 minutes
- customThe sealed reaction vessel
- filtrationThe crude mixture was filtered through an SCX-2 acidic resin cartridge
- washeluting with 2 M ammonia in methanol
- concentrationThe basic filtrate was concentrated
- custompurified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-58171aae7fd94b37a68ecf7ba112ffeb
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08530468B2
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