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

HRID 2176842

Reaktionsgleichung

Reaktionsgleichung von HRID 2176842
[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>C1COCC1>[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-pyridineAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a room temperature solution of 2,6-dimethyl-3-pyridinol (3 g, 24.35 mmol) in THF (30 ml) was added cesium carbonate (15.87 g, 48.71 mmol) and 3,4-difluoro-1-nitro-benzene (3.87 g, 24.35 mmol). The reaction mixture was heated at reflux for 2 hours. After cooling to room temperature the solids were filtered off and the filtrate was evaporated till dryness. The crude product was purified by column chromatography (silica gel; DCM to DCM/MeOH(NH3) up to 2% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 9 (5.88 g, 92%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationwere filtered off
  4. customthe filtrate was evaporated till dryness
  5. customThe crude product was purified by column chromatography (silica gel; DCM to DCM/MeOH(NH3) up to 2% as eluent)
  6. customThe desired fractions were collected
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6b03cd9d70f24a349c02bb89551cb28b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067891B2

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