Dichloromethane → 4-(5-methoxypyridin-3-yl)-9H-carbazole

HRID 1877452

Reaktionsgleichung

Reaktionsgleichung von HRID 1877452
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[N:7][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl.FC(F)(F)S(O[C:27]1[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)(=O)=O>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:27]2[C:39]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[NH:32][C:31]=3[CH:30]=[CH:29][CH:28]=2)[CH:6]=[N:7][CH:8]=1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27630875-Methoxypyridine-3-boronic AcidHCID 583383234-Trifluoromethanesulphonyloxycarbazole

Produkt 1

HCID 673084644-(5-methoxypyridin-3-yl)-9H-carbazoleAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

0.54 g of (5-methoxypyridin-3-yl)boronic acid, 3.3 g of caesium carbonate and 93 mg of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride as a complex with dichloromethane (1/1) [PdCl2(dppf)CH2Cl2] are successively added, under argon, to a solution of 0.8 g of 4-trifluoromethanesulphonyloxycarbazole, obtained in stage 1 of Example 1, in a mixture of 37 ml of dioxane and 12 ml of water. The reaction mixture is refluxed for 3 and a half hours, filtered through celite and concentrated under reduced pressure. The residue is subsequently purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (75/25 by volume), so as to give 0.7 g of 4-(5-methoxypyridin-3-yl)-9H-carbazole in the form of a colourless oil, the characteristics of which are the following:

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 3 and a half hours
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is subsequently purified by silica gel chromatography, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (75/25 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-b1e5a10509c34e24a2406d19495396e3
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309721B2

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