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1,10-Phenanthroline → 6-(2-Fluorophenoxy)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine

HRID 1401111
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1401111
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)(O)[O-].[Na+].Cl[C:35]1[N:40]=[CH:39][C:38]2[N:41]=[C:42]([C:44]3[CH:49]=[C:48]([CH3:50])[C:47]([O:51][CH3:52])=[C:46]([CH3:53])[CH:45]=3)[O:43][C:37]=2[CH:36]=1>CN(C)C=O.[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:35]1[N:40]=[CH:39][C:38]2[N:41]=[C:42]([C:44]3[CH:45]=[C:46]([CH3:53])[C:47]([O:51][CH3:52])=[C:48]([CH3:50])[CH:49]=3)[O:43][C:37]=2[CH:36]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 13181,10-PhenanthrolineHCID 97072-FluorophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 717431286-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridine

Produkt 1

HCID 71186536
6-(2-Fluorophenoxy)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine
Ausbeute 10,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

In a microwaveable vessel, 0.65 g of 6-chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine were dissolved in 12 ml of absolute N,N-dimethylformamide, and 0.25 g of 2-fluorophenol, 0.88 g of cesium carbonate, 21 mg of copper (I) iodide and 40 mg of 1,10-phenanthroline were added. In a microwave reactor, the reaction was heated at 200° C. for 1 h. For work-up, the mixture was added to saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium bisulaite solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by means of preparative HPLC, giving 86 mg (10%) of product.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous sodium bisulaite solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c61f3af7c74e466e89ab391eb6be26e2
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08907093B2

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