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Cesium carbonate → Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(3,3-dimethyl-2-oxobutoxy)nicotinate

HRID 8809
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 8809
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[CH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:14][CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[N:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 21642BromopinacoloneHCID 21984816Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

Produkt 1

HCID 21984933Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-(3,3-dimethyl-2-oxobutoxy)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A 25 mL rb flask was charged with 1.111 g (2.97 mmol) of the product of Step B, 1.451 g (4.45 mmol) Cs2CO3, 10 mL DMF and finally 0.5 mL (3.71 mmol) of bromopinacolone. The reaction mixture was stirred at room temperature 1 h then partitioned between EtOAc and water. The organic layer was washed with water, brine, then dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Aufarbeitung

  1. customthen partitioned between EtOAc and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on a silica gel flash chromatography column
  7. washeluted with 0–20% EtOAc-hexane
  8. customEvaporation of the purified fractions
  9. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7fd2ced16c8e4fd7949b21830373d6d1
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07091216B2

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