Sodium hydride → 3-(3-Bromo-6,7-dihydro-5H-[1]pyrindin-7-yl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine
Reaktionsgleichung
[H-].[Na+].[CH2:3]([C:5]1[NH:15][C:8]2=[N:9][C:10]([CH3:14])=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)[CH3:4].[Br:16][C:17]1[CH:18]=[N:19][C:20]2[CH:21](Cl)[CH2:22][CH2:23][C:24]=2[CH:25]=1.[Na+].[Br-]>O1CCOCC1>[Br:16][C:17]1[CH:18]=[N:19][C:20]2[CH:21]([N:15]3[C:8]4=[N:9][C:10]([CH3:14])=[CH:11][C:12]([CH3:13])=[C:7]4[N:6]=[C:5]3[CH2:3][CH3:4])[CH2:22][CH2:23][C:24]=2[CH:25]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of NaH, 60% in oil, (163 mg) in 3 mL of 1,4-dioxane was added 2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (1.1 gm) at room temperature and stirred for 30 minutes. Then 3-bromo-7-chloro-6,7-dihydro-5H-[1]pyrindine (500 mg, 2.15 mM) in 2 mL of 1,4-dioxane and anhydrous NaBr (442 mg) were added to the solution and the reaction was heated to 100° C. for 24 hours. The reaction was then cooled to room temperature, concentrated to dryness, and extracted into ethyl acetate from water. The organic layers were dried over MgSO4, filtered, and evaporated to dryness. The residue was purified by chromatography on silica gel to yield 110 mg of product.
Aufarbeitung
- temperatureThe reaction was then cooled to room temperature
- concentrationconcentrated to dryness
- extractionextracted into ethyl acetate from water
- dry with materialThe organic layers were dried over MgSO4
- filtrationfiltered
- customevaporated to dryness
- customThe residue was purified by chromatography on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-0ba5798fcf0c4766be13fff8fba00fe5
- Quelldatensatz
- uspto-grants-1994_08
- Patentnummer
- US05338740
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