Ethyl bromoacetate → HCID 19434994, compound

Participants

Reaction Conditions

Reaction Steps

1.02 g (2.62mmol) of 5-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one obtained in Example 66 was dissolved in 30 mL of dimethylformamide under argon atmosphere, 5.8 mL (52.3 mmol) of ethyl bromoacetate and 1.80 g (13.1 mmol) of potassium carbonate were added and the mixture was stirred at 100° C. for 21 hours. The reaction solution was cooled on ice, an aqueous saturated solution of ammonium chloride was added and the precipitated crystals were collected by filtration. The mother liquor was extracted with ethyl acetate, and the organic layer was washed with water and with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the residue was added to the above crystals and the mixture was purified by silica gel column chromatography (chloroform:acetonitrile=25:1) to give 824 mg of 5-ethoxycarbonylmethylamino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one (yield: 66%).

Provenance & Evidence