반응 #1964659

반응 방정식

[5-(benzyloxy)pyridin-3-yl]boronic acid

caesium carbonate

dichloromethane

4-trifluoromethanesulphonyloxycarbazole

→

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

수율 80.2%

용매

dioxane

water

반응 조건

후처리

1. 1
   온도The reaction mixture is refluxed for 5 hours
2. 2
   여과filtered through celite and
3. 3
   농축concentrated under reduced pressure
4. 4
   기타The residue is subsequently purified by silica gel chromatography, elution
5. 5
   workup.ADDITIONbeing carried out with a mixture of cyclohexane and ethyl acetate (80/20 by volume)

실험 절차

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:

출처