3-Nitrophenylboronic Acid → N-(2-Bromo-5-cyano-3-methoxy-6-methyl-3'-nitrobiphenyl-4-yl)-2,2-dimethylpropionamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide (I-6) (965 mg, 2.14 mmol), 3-nitrophenylboronic acid (375 mg, 2.25 mmol), tripotassium phosphate (74-85%, 1.23 g, 4.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (247 mg, 0.214 mmol) were added to a 50-ml eggplant-type flask, followed by purging with nitrogen. N,N-Dimethylformamide (20 ml) was injected into it with a syringe, followed by stirring at 95° C. for 4 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine, an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1→4:1) to obtain the entitled compound (645 mg, 68%) as a pale yellow solid.

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