反応 #85471

反応方程式

sodium hydride

3-amino-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

2,4-dimethoxyphenylsulfonyl chloride

→

title compound

収率 41.1%

3-Amino-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

収率 41.1%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度while cooling in an ice bath
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 15 min
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄The organic phase was washed with saturated sodium chloride solution
5. 5
   乾燥dried over magnesium sulfate
6. 6
   その他the solvent was evaporated
7. 7
   その他The residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 3% methanol in ethyl acetate)

実験手順

80 mg (1.68 mmol) of sodium hydride (60% dispersion in mineral oil) were added in portions to a solution of 350 mg (1.12 mmol) of 3-amino-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile in 15 ml of anhydrous dimethylformamide under a nitrogen atmosphere and while cooling in an ice bath. The mixture was stirred at 0° C. for 10 min and then 398 mg (1.68 mmol) of 2,4-dimethoxyphenylsulfonyl chloride were added, and the mixture was stirred at room temperature for 15 min. The reaction mixture was poured into ice-water and then extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 3% methanol in ethyl acetate). 236 mg of the title compound were obtained as a white solid.

出典