Phosphorus oxychloride → 4-(2-Benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole

HRID 1445763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445763
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([NH:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])[C:12](=O)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]=[C:16]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[F:24])[O:25][C:12]=1[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 58951463N-[1-(2-Benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide2×

Produkt 1

HCID 589514114-(2-Benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirring solution of N-[1-(2-benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide (1.0 mmol) (See Intermediate 36) in dimethylformamide (0.25M), slowly add phosphorus oxychloride (3.0 mmol) and heat to 90° C. for 2.5 hours. After this time, remove the heat and carefully add water (same amount as DMF) and allow the reaction to cool to room temperature before extracting with ether. Wash organics with water and brine. Dry the organics with sodium sulfate, filter and concentrate in vacuo. Purify via radial chromatography eluting with ethyl acetate and hexane. MS (m/e) (79Br/81Br): 390.2/392.2 (M+1)

Aufarbeitung

  1. customAfter this time, remove the
  2. temperatureheat
  3. customthe reaction
  4. extractionbefore extracting with ether
  5. dry with materialDry the organics with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify via radial chromatography
  9. washeluting with ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-65ef94116c9449c6bca22a5257c7de1b
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666871B2

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