Acetone → 6-(2-Chlorophenylamino)-7-fluoro-3-methyl-benzo[c]-isoxazole-5-carboxylic acid methyl ester

HRID 857513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857513
[N-:1]=[N+]=[N-].[Na+].[CH3:5][O:6][C:7](=[O:27])[C:8]1[CH:13]=[C:12]([C:14](=[O:16])[CH3:15])[C:11](F)=[C:10]([F:18])[C:9]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26].CC(C)=O>CCOC(C)=O.O>[CH3:5][O:6][C:7]([C:8]1[C:9]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])=[C:10]([F:18])[C:11]2=[N:1][O:16][C:14]([CH3:15])=[C:12]2[CH:13]=1)=[O:27]

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 865967735-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

Produkt 1

HCID 688605096-(2-Chlorophenylamino)-7-fluoro-3-methyl-benzo[c]-isoxazole-5-carboxylic acid methyl esterAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium azide (128 mg, 1.95 mmol) was added to a mixture of 5-acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (6) (601 mg, 1.59 mmol) in 3:1 acetone:water (16 ml) and heated to reflux. After 16 hours, the reaction mixture was cooled to room temperature, and diluted with EtOAc and water. The organic layer was washed with water, dried (MgSO4) and concentrated. The resulting residue was diluted with water (8 mL) and heated to reflux. After 5 hours, the mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water, dried (MgSO4) and concentrated. Purification by flash column chromatography using the Biotage system (20% EtOAc in hexanes) provided the desired product (55) (410 mg, 77%).

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionThe resulting residue was diluted with water (8 mL)
  5. temperatureheated to reflux
  6. waitAfter 5 hours
  7. temperaturethe mixture was cooled to room temperature
  8. additiondiluted with EtOAc
  9. washThe organic layer was washed with water
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c46452fe21c241a08c7ead59906e6c01
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144907B2

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