Cesium carbonate → 5-[9-(4-cyano-3-fluorophenyl)-9H-carbazol-4-yl]pyridine-2-carbonitrile

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Reaction Steps

0.267 g of 4-bromo-2-fluorobenzonitrile, 1.1 g of caesium carbonate, 0.06 g of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) and 0.02 g of palladium acetate are successively added, under argon, to a solution of 0.24 g of 5-(9H-carbazol-4-yl)pyridine-2-carbonitrile in 10 ml of dioxane. The reaction mixture is refluxed for 3 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 (85/15 by volume), so as to give 0.2 g of 5-[9-(4-cyano-3-fluorophenyl)-9H-carbazol-4-yl]pyridine-2-carbonitrile in the form of an off-white solid, the characteristics of which are the following:

Provenance & Evidence