Toluene → 5-(3-Cyanophenyl)-2,3-diphenylpyrazine

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Reaction Steps

First, 1.02 g of 2,3-diphenyl-5-chloropyrazine, 0.62 g of 3-cyanophenylboronic acid, 0.15 g of tetrakis triphenylphosphine palladium(0) (abbreviation: Pd(PPh3)4), 10 mL of toluene, 1.5 mL of ethanol, 1.16 g of potassium carbonate, 4.2 mL of water were put in an eggplant-type flask with a reflux pipe, and the atmosphere in the flask was substituted with argon. Then, irradiation with microwave (2.45 GHz, 100 W to 150 W) was performed for 45 minutes to cause a reaction. Water was added to this mixture and dichloromethane was used as an extraction solvent, so that an organic layer was extracted. The obtained organic layer was dried with anhydrous magnesium sulfate. After the drying, the solution was filtrated. After a solvent of this solution was distilled off, the residue obtained by the distillation was purified by silica gel column chromatography which uses a mixture solution of dichloromethane and ethyl acetate as a developing solvent to obtain a white powdered solid in a yield of 42%. Note that the irradiation with a microwave was performed using a microwave synthesis system (Discover, produced by CEM Corporation). A synthesis scheme of Step 1 is shown by the following (a-1).

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