Cesium carbonate → 4-{4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazol-9-yl}-2-fluorobenzonitrile

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Reaction Steps

1.08 g of 4-bromo-2-fluorobenzonitrile, 4.48 g of caesium carbonate, 0.25 g of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) and 0.08 g of palladium acetate are successively added, under argon, to a solution of 1.27 g of 4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazole in 100 ml of dioxane. The reaction mixture is refluxed for 2 and a half hours, cooled to ambient temperature, 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 (80/20 by volume), so as to give 1.1 g of 4-{4-[5-(benzyloxy)pyridin-3-yl]-9H-carbazol-9-yl}-2-fluorobenzonitrile in the form of a colourless oil, the characteristics of which are the following:

Provenance & Evidence