1-Iodopentane → 2-[4-[N-acetyl-N-(1-pentyl)amino]-3-fluorophenyl]-6,8-difluoro-7-methyl-5-(1-pentylamino)-4H-1-benzopyran-4-one

Participants

Reaction Steps

510 mg (1.41 mmol) of 2-(4-acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one obtained in Example 109 (1) was dissolved in 30 mL of dimethylformamide under argon atmosphere, 58 mg (1.5 mmol) of sodium hydride (60% oil dispersion) and 0.37 mL (2.8 mmol) of 1-iodopentane were added under ice-cooling and the mixture was stirred at room temperature for 4 hours. The reaction solution was cooled on ice, 117 mg (2.93 mmol) of sodium hydride (60% oil dispersion) and 0.37 mL (2.8 mmol) of 1-iodopentane were added and the mixture was stirred at room temperature for 50 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 (chloroform) to give 153 mg of 2-[4-[N-acetyl-N-(1-pentyl)amino]-3-fluorophenyl]-6,8-difluoro-7-methyl-5-(1-pentylamino)-4H-1-benzopyran-4-one (yield: 22%).

Provenance & Evidence