Iodine → 3-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carboxamide

HRID 561208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561208
[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH2:15][CH:14]([C:16]([NH2:18])=[O:17])[O:13][N:12]=2)[CH2:7][CH2:6]1.C([O-])(=O)C.[Na+].II.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClC1C=CC=CC=1.CCOC(C)=O.O>[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]([NH2:18])=[O:17])[O:13][N:12]=2)[CH2:7][CH2:6]1

Komponenten

8

Edukt 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 517045Sodium AcetateHCID 666968003-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]-4,5-dihydroisoxazole-5-carboxamide

Produkt 1

HCID 533885293-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 7964ChlorobenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred suspension of 3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-4,5-dihydroisoxazole-5-carboxamide (2.3 g, 5.96 mmol) and sodium acetate (1.3 g, 15.85 mmol) in chlorobenzene (15 mL) was added iodine (2 g, 7.88 mmol). The mixture was heated at reflux temperature for 3 h. After cooling, a solution of Na2S2O3, water and EtOAc were added. The mixture was stirred for 5 min and filtered through celite to remove the insoluble material. The organic layer was then separated, washed with brine, dried (Na2SO4) and concentrated. The residue was triturated with Et2O to give the title compound as light brown powder.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. temperatureAfter cooling
  4. filtrationfiltered through celite
  5. customto remove the insoluble material
  6. customThe organic layer was then separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-091711a9d51d4572a203552b8c604b9d
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063224B2

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