Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[CH:7]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:18]=[CH:17][N:16]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:17]3[CH:18]=[C:19]([CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26]4)[CH:20]=[CH:15][N:16]=3)[N:10]=2)[CH:7]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 6-bromoimidazo[1,2-a]pyridin-2-amine (200 mg; 0.94 mmol) in dry THF (4 mL) was added NaH (90 mg; 3.76 mmol) in portions at 0° C. The reaction mixture was stirred at r.t. for half an hour. Then 2-chloro-4-(pyrrolidin-1-ylmethyl)pyridine (222 mg, 1.1 mmol) was added. The mixture was heated to 120° C. for 24 hrs. The mixture was quenched by addition of H2O (20 mL) slowly at 0° C., extracted with DCM (30 mL×3). The combined organic phases were concentrated under reduced pressure and purified by column chromatography on silica (DCM:MeOH=15:1) to obtain 6-bromo-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)imidazo[1,2-a]pyridin-2-amine (110 mg, yield 80%) as a brown solid.
Aufarbeitung
- temperatureThe mixture was heated to 120° C. for 24 hrs
- customThe mixture was quenched by addition of H2O (20 mL) slowly at 0° C.
- extractionextracted with DCM (30 mL×3)
- concentrationThe combined organic phases were concentrated under reduced pressure
- custompurified by column chromatography on silica (DCM:MeOH=15:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-292c41f330fd43c89580151888e52c3d
- Quelldatensatz
- uspto-grants-2016_02
- Patentnummer
- US09266874B2
Verknüpfte Notizen
Wird geladen…