Pyrrole → 5-Methyl-3-phenyl-6-(4-pyrrol-1-ylmethyl-phenyl)-5H-isoxazolo[4,5-c]pyridin-4-one

HRID 8313

Reaktionsgleichung

Reaktionsgleichung von HRID 8313
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]([CH3:15])[C:13](=[O:16])[C:12]3[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:18][O:19][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:32]1[CH:36]=[CH:35][CH:34]=[CH:33]1>CN(C=O)C>[CH3:15][N:14]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][N:32]3[CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:8][CH:7]=2)=[CH:10][C:11]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]=2[C:13]1=[O:16]

Komponenten

5

Edukt 3

HCID 8027PyrroleHCID 10796Cesium carbonateHCID 220155615-Methyl-3-phenyl-6-(p-bromomethylphenyl)-isoxazolo[4,5-c]pyridin-4(5H)-one

Produkt 1

HCID 220155845-Methyl-3-phenyl-6-(4-pyrrol-1-ylmethyl-phenyl)-5H-isoxazolo[4,5-c]pyridin-4-oneAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 198 mg (0.5 mmol) of 6-(4-bromomethyl-phenyl)-5-methyl-3-phenyl-5H-isoxazolo[4,5-c]pyridin-4-one in 2.5 ml of DMF is added 326 mg (1.0 mmol, 2.0 eq.) of caesium carbonate and 0.05 ml (0.6 mmol, 1.2 eq.) of pyrrole. After stirring 16 h at room temperature the solvent is removed in vacuo and the residue taken up in CH2Cl2. The organic phase is washed with NaHCO3-solution, dried over Na2SO4 and concentrated. Flash chromatography yields 34 mg (18%) of the desired compound as a white solid. Mass spectrum: m/z (M+H)+: 382.1

Aufarbeitung

  1. customis removed in vacuo
  2. washThe organic phase is washed with NaHCO3-solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f214d5cbf2a241b5a58c6a1faf760ae1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087756B2

Verknüpfte Notizen

Wird geladen…