1,10-Phenanthroline → 6-(Azetidin-3-yloxy)imidazo[1,2-a]pyridine

HRID 1021312

Reaktionsgleichung

Reaktionsgleichung von HRID 1021312
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[OH:11][CH:12]1[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(C(F)(F)F)=O>[Cu](I)I.ClCCl.O.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[NH:14]1[CH2:15][CH:12]([O:11][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[CH:7]=2)[CH2:13]1

Komponenten

11

Edukt 5

HCID 13181,10-PhenanthrolineHCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 27643276-Iodoimidazo(1,2-a)pyridine

Produkt 1

HCID 683090446-(Azetidin-3-yloxy)imidazo[1,2-a]pyridineAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6-Iodoimidazo[1,2-a]pyridine (400 mg), tert-butyl 3-hydroxyazetidine-1-carboxylate (500 mg), and toluene (2 ml) were mixed, and copper iodide (I) (40 mg), 1,10-phenanthroline (60 mg), and cesium carbonate (1 g) were added thereto, followed by stirring at 100° C. overnight. CHCl3 and water were added to the reaction mixture, and the organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The purified product thus obtained was mixed with dichloromethane (5 ml), and TFA (1.5 ml) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain 6-(azetidin-3-yloxy)imidazo[1,2-a]pyridine (189 mg).

Aufarbeitung

  1. dry with materialthe organic layer was dried over Na2SO4
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
  4. customThe purified product thus obtained
  5. additionwas added
  6. stirringby stirring at room temperature for 3 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe residue was purified by basic silica gel column chromatography (CHCl3/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-ac65f3f823ba49ada14e78697e3c2ed4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716470B2

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