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Benzyl Alcohol → 3-Benzyloxy-1-(7-methoxy-2-trifluoromethyl-pyrazolo[1,5-a]pyridine-4-yl)-propane-1-one

HRID 2357939
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Reaktionsgleichung

Reaktionsgleichung von HRID 2357939
[CH3:1][O:2][C:3]1[N:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=[C:7]2[C:6]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:5][CH:4]=1.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[CH2:20]([O:27][CH2:18][CH2:17][C:16]([C:6]1[C:7]2[N:8]([N:9]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:11]=2)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
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Komponenten

4

Edukt 2

HCID 244Benzyl Alcohol2×HCID 593893617-Methoxy-4-propionyl-2-trifluoromethyl-pyrazolo[1,5-a]pyridine

Produkt 1

HCID 593892843-Benzyloxy-1-(7-methoxy-2-trifluoromethyl-pyrazolo[1,5-a]pyridine-4-yl)-propane-1-oneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of the compound of Example 319 (3.42 g) and benzyl alcohol (1.37 g) in dichloromethane (50 mL) was added to dichloro bis(acetonitrile) palladium (II) (329 mg) in a stream of argon gas. The mixture was stirred at room temperature overnight, followed by addition of benzyl alcohol (500 mL) and stirring overnight. The insoluble material was removed by filtration through Celite. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2). The product was further purified by amino-silica gel column chromatography (hexane:ethyl acetate=3:2) to afford the title compound as a pale yellow powder (2.47 g).

Aufarbeitung

  1. stirringstirring overnight
  2. customThe insoluble material was removed by filtration through Celite
  3. customThe solvent was evaporated
  4. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)
  5. customThe product was further purified by amino-silica gel column chromatography (hexane:ethyl acetate=3:2)

Quellen und Nachweise

ORD-Eintrag
ord-beb82b0a1285494388793e6d60fd6f56
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07763617B2

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