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HRID 1877477Erstellt: 24. Oktober 2026

Dichloromethane → 4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazole

https://huagongshe.com/de/reaction/1877477

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDichloromethaneHCID 6344—
EduktCesium carbonateHCID 10796—
Edukt(5-(Benzyloxy)pyridin-3-yl)boronic acidHCID 53398533—
Edukt4-TrifluoromethanesulphonyloxycarbazoleHCID 58338323—
KatalysatorBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
LösungsmittelWaterHCID 962—
Lösungsmittel1,4-DioxaneHCID 31275—
Produkt4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazoleHCID 6730864480,2%

Reaktionsschritte

1.63 g of [5-(benzyloxy)pyridin-3-yl]boronic acid, 6.4 g of caesium carbonate and 0.182 g 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 1.57 g of 4-trifluoromethanesulphonyloxycarbazole, obtained in stage 1 of Example 1, in a mixture of 71 ml of dioxane and 24 ml of water. The reaction mixture is refluxed for 5 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 (80/20 by volume), so as to give 1.4 g of 4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazole in the form of a pale yellow oil, the characteristics of which are the following:

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08309721B2
Quelldatensatzuspto-grants-2012_11
ORD IDord-e6b179653e9f4852a66b93f250833491
Quellennotizuspto-grants-2012_11