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

Participants

Reaction Steps

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:

Provenance & Evidence