Acetyl chloride → 1-[2-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]ethan-1-one

HRID 731735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731735
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH:9]([C:12]1[CH:20]=[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1)([CH3:11])[CH3:10].C([O-])(O)=O.[Na+]>ClCCl.CCOC(C)=O>[CH:9]([C:12]1[C:20]([C:5](=[O:7])[CH3:6])=[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1)([CH3:11])[CH3:10]

Komponenten

7

Edukt 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Produkt 1

HCID 159338551-[2-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]ethan-1-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Solid aluminum chloride (0.82 g, 2 equivalents) was added to a solution of acetyl chloride (0.24 mL, 1.1 equivalents) in 1 mL of dichloromethane and the solution was stirred at room temperature for 40 minutes. Neat 2-isopropylpyrazolo[1,5-a]pyridine (0.5 g, 1 equivalent) was added dropwise to this solution at room temperature (exotherm was observed), and the resulting solution was stirred at room temperature for 20 hours and worked up with EtOAc and saturated NaHCO3. The crude product was purified by silica gel flash column chromatography to give 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)ethanone (0.29 g, 46% yield) as a solid. Compound 1080.

Aufarbeitung

  1. stirringthe resulting solution was stirred at room temperature for 20 hours
  2. customThe crude product was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c9c43f1d4ff747c68bc55a28800a3668
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585875B2

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