2-Methyl-5-Nitroaniline → 2-[(4-Chloro)pyridin-2-ylamino]-1-methyl-4-nitrobenzene

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To 2.00 g of 2,4-dichloropyridine, 2.26 g of 2-methyl-5-nitroaniline, 121 mg of palladium (II) acetate, 336 mg of (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(±)-BINAP] and 6.16 g of cesium carbonate, 120 ml of toluene was added, and then the mixture was stirred with heating at 70° C. for 23 hours under an argon atmosphere. After insolubles were removed by filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain a crude product. The crude product was washed with diethyl ether to obtain 1.22 g of the objective compound as yellow crystals.

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