1,10-Phenanthroline → 2-(5-Bromo-2-pyridinyl)benzoxazole

HRID 521547

Reaktionsgleichung

Reaktionsgleichung von HRID 521547
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](Cl)=[O:17])=[N:14][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]I.C(Cl)Cl.O1CCOCC1>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[O:17][C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)=[N:14][CH:15]=1

Komponenten

8

Edukt 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 119922-BromoanilineHCID 190907715-Bromo-pyridine-2-carbonyl chloride

Produkt 1

HCID 469416132-(5-Bromo-2-pyridinyl)benzoxazoleAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-bromoaniline (3.90 g, 22.7 mmol), 5-bromopyridine-2-carbonyl chloride (5.00 g, 22.7 mmol), Cs2CO3 (14.78 g, 45.36 mmol), 1,10-phenanthroline (0.409 g, 2.27 mmol), CuI (0.216 g, 1.13 mmol) and anhydrous 1,4-dioxane (40 mL) was degassed with argon for about 40 min while stirring. The stirring reaction mixture was then maintained under argon at about 120° C. for about 40 h. Upon completion, the reaction was cooled to RT and poured over CH2Cl2 (300 mL). The organics were then washed with sat. NaHCO3, H2O and brine, dried over MgSO4, filter and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO2, 4:1 dichloromethane-hexanes) and subsequent recrystallization from hexanes afforded compound 11 (1.86 g, 30% yield) as colorless fibers.

Aufarbeitung

  1. customwas degassed with argon for about 40 min
  2. customThe stirring reaction mixture
  3. temperatureUpon completion, the reaction was cooled to RT
  4. washThe organics were then washed with sat. NaHCO3, H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfilter
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product

Quellen und Nachweise

ORD-Eintrag
ord-3c0af32c96b544d6aa712ca19029fe13
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328086B2

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