Cesium carbonate → 3-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine

HRID 889638

Reaktionsgleichung

Reaktionsgleichung von HRID 889638
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F>CN(C=O)C>[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[O:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 707322,6-Dimethyl-3-pyridinolHCID 1230531,2-Difluoro-4-nitrobenzene

Produkt 1

HCID 592873193-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

2,6-Dimethyl-pyridin-3-ol (3.0 g, 24.35 mmol) and cesium carbonate (15.87 g, 48.71 mmol) were added to a solution of 3,4-difluoronitrobenzene (3.87 g, 24.35 mmol) in DMF (30 ml). The mixture was heated at 140° C. for 2 hours. After cooling to room temperature it was filtered through diatomaceous earth and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; 2% methanol/DCM as eluent) to yield intermediate D14 (5.88 g, 92%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature it
  2. filtrationwas filtered through diatomaceous earth
  3. customthe solvent evaporated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel; 2% methanol/DCM as eluent)
  5. customto yield intermediate D14 (5.88 g, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-ff82bd1a5117480abb87aec61fb563ad
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252937B2

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