反应 #1964638

反应方程式

[6-(hydroxymethyl)pyridin-3-yl]boronic acid

caesium carbonate

dichloromethane

4-trifluoromethanesulphonyloxycarbazole

→

[5-(9H-carbazol-4-yl)pyridin-2-yl]methanol

收率 47.4%

溶剂

dioxane

water

反应条件

后处理

1. 1
   温度The reaction mixture is refluxed for 5 hours
2. 2
   浓缩concentrated under reduced pressure
3. 3
   workup.ADDITIONThe residue is subsequently taken up with a mixture of dichloromethane and ethyl acetate
4. 4
   workup.ADDITIONtreated with carbon black
5. 5
   过滤filtered through celite and
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他The residue is purified by silica gel chromatography, elution
8. 8
   workup.ADDITIONbeing carried out with a mixture of cyclohexane and ethyl acetate (55/45 by volume)

实验过程

0.54 g of [6-(hydroxymethyl)pyridin-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(dppO'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 5 hours, cooled to ambient temperature and concentrated under reduced pressure. The residue is subsequently taken up with a mixture of dichloromethane and ethyl acetate, treated with carbon black, filtered through celite and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (55/45 by volume), so as to give 0.33 g of [5-(9H-carbazol-4-yl)pyridin-2-yl]methanol in the form of a colourless oil, the characteristics of which are the following:

来源