Cesium carbonate → 1-{[3-Acetyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridin-2-yl]oxy}-3,3-dimethylbutan-2-one

HRID 8810

Reaktionsgleichung

Reaktionsgleichung von HRID 8810
[C:1]([C:4]1[C:5](=[O:24])[NH:6][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>CN(C=O)C>[C:1]([C:4]1[C:5]([O:24][CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[N:6][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:9]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 21642BromopinacoloneHCID 670199153-Acetyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridin-2(1H)-one

Produkt 1

HCID 219848171-{[3-Acetyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridin-2-yl]oxy}-3,3-dimethylbutan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a 25 mL rb flask equipped with a magnetic stir bar was added 0.309 g(0.86 mmol) of the product of Step A, 0.422 g (1.29 mmol) of cesium carbonate, 3 mL DMF and finally 145 μL of 1-bromopinacolone was added. The reaction mixture was stirred at room temperature for 1.5 h then partitioned between EtOAc and water. The organic layer was separated, washed with 10% aq. NaHSO4, water, brine, dried (MgSO4), filtered and evaporated. The residue was purified on s silica gel flash chromatography column eluted with 0–10% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Aufarbeitung

  1. customTo a 25 mL rb flask equipped with a magnetic stir bar
  2. additionwas added
  3. customthen partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with 10% aq. NaHSO4, water, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on s silica gel flash chromatography column
  10. washeluted with 0–10% EtOAc-hexane
  11. customEvaporation of the purified fractions
  12. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ea6785e61a9d489682d374698133b827
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091216B2

Verknüpfte Notizen

Wird geladen…