Butyl iodide → 2-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-butylamino-6,8-difluoro-4H-1-benzopyran-4-one

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Reaction Steps

1.01 g (2.35 mmol) of 2-[4-[N-acetyl-N-(3-azidopropyl) amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one obtained in Example 79 was dissolved in 30 mL of dimethylformamide under argon atmosphere, 1.34 mL (11.8 mmol) of 1-iodobutane and 190 mg (4.75 mmol) of sodium hydride (60% oil dispersion) were added and the mixture was stirred at room temperature for 45 minutes. An aqueous solution of ammonium chloride was added to the reaction solution and the mixture was extracted twice with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to give 726 mg of 2-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-butylamino-6,8-difluoro-4H-1-benzopyran-4-one (yield: 63%).

Provenance & Evidence