1859-75-2

To an oven-dried round-bottomed flask containing K2CO3 (3.46 g, 25 mmol, 1 equiv) suspended in anhydrous DMF (15 mL) was added 1-(2-aminophenyl)ethan-1-one (3.04 mL, 25 mmol). The reaction mixture was stirred at room temperature for 15 minutes under argon protection. Subsequently, anhydrous DMF solution of MeI (1.56 mL, 25 mmol, 1 equiv) was added slowly and dropwise to the reaction mixture. Stirring of the reaction mixture was continued at room temperature for 3 days. Upon completion of the reaction, the reaction mixture was diluted with H2O (60 mL) and extracted with ethyl acetate (340 mL). The organic phases were combined, washed sequentially with water (50 mL) and brine (50 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuum and purified by column chromatography (3%-5% petroleum ether solution of ethyl acetate) to afford 1-(2-(methylamino)phenyl)ethan-1-one (1.98 g, 53%) as yellow crystals. Next, 1-(bromomethyl)-2-iodobenzene (1.48 g, 5 mmol), 1-(2-(methylamino)phenyl)ethan-1-one (895 mg, 6 mmol, 1.1 eq.), K2CO3 (1.38 g, 10 mmol, 2 eq.), and acetonitrile (5 mL) were added to an oven-dried, high-pressure sealed tube. The reaction mixture was stirred at 85 °C for 4 days. After completion of the reaction, it was cooled to room temperature, diluted with H2O (20 mL) and extracted with dichloromethane (315 mL). The organic phases were combined, washed with brine (40 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuum and purified by column chromatography (petroleum ether solution of 5% ethyl acetate) to afford 1-(2-((2-iodobenzyl)(methyl)amino)phenyl)ethan-1-one (1.45 g, 79%) as orange crystals.

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