2-Pyridineacetic acid, hydrochloride (1:1) → 2-Pyridin-2-yl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone
Reaktionsgleichung
CO[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].Cl.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21]C(O)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (200 mg, 1.13 mmol) and 2-pyridinyl-acetic acid hydrochloride (440 mg, 2.53 mmol) in anhydrous THF (10 mL) was added LiHMDS (1.0 M in THF, 10 mL, 10.0 mmol) at −78° C. The solution was stirred at −78° C. for 30 min and was allowed to warm up to RT. After stirring at RT for another 30 min, the reaction mixture was heated under reflux for 14 h. The solvent was then evaporated, the residue was taken up to ethyl acetate (50 mL), and washed with aq. NaHCO3. The organic layer was dried over MgSO4, filtered, and evaporated. The residue was used directly for the next reaction.
Aufarbeitung
- temperatureto warm up to RT
- stirringAfter stirring at RT for another 30 min
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 14 h
- customThe solvent was then evaporated
- washwashed with aq. NaHCO3
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue was used directly for the next reaction
Quellen und Nachweise
- ORD-Eintrag
- ord-ebe10ceb71664519a80050fdc239dbbd
- Quelldatensatz
- uspto-grants-2008_11
- Patentnummer
- US07446199B2
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