Sodium Iodide → 2-[4-[N-Acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

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Reaction Steps

1.81 g of Compound 27 was dissolved in 60 ml of dimethylformamide, 208 mg of sodium hydride (60% oil dispersion), 1.67 g of N-(3-bromopropyl)phthalimide and 156 mg of sodium iodide were added and the mixture was stirred at room temperature for 2.5 hours. Additional 104 mg of sodium hydride (60% oil dispersion) and 697 mg of N-(3-bromopropyl)phthalimide were added and the mixture was stirred at room temperature for 1.8 hours. Additional 62.4 mg of sodium hydride (60% oil dispersion) and 418 mg of N-(3-bromopropyl)phthalimide were added and the mixture was stirred at room temperature for 2 hours. An aqueous solution of ammonium chloride was added to the reaction solution, the solvent was distilled off under reduced pressure and the residue was extracted once with chloroform. The chloroform layer was washed with an aqueous saturated solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform:methanol=100:1-60:1) and recrystallized from chloroform/n-hexane to give 1.72 g (62%) of Compound 28.

Provenance & Evidence