Ethanol → 5-Ethoxy-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one
反応式
[F:1][C:2]1[C:3](/[C:12](/I)=[CH:13]/[C:14](=O)[C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[H-].[Na+].[CH3:24][CH2:25][OH:26]>>[CH2:25]([O:26][C:12]1[CH:13]=[C:14]([C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)[C:5]2[C:6](=[O:11])[NH:7][C:8]3[C:4]=2[C:3]=1[C:2]([F:1])=[CH:10][CH:9]=3)[CH3:24]参加物
実験手順
To a suspension of (Z)-5-fluoro-4-[1-iodo-3-oxo-3-(1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one (from Example 8 above) (19.8 mg, 0.05 mmol) in EtOH (5 mL) was added NaH (Aldrich, 60%, 0.1 g, 2.5 mmol) in portions at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was heated under reflux for 2 hours. The reaction was quenched by pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by preparative TLC (silica gel, 50% ethyl acetate in hexanes) to afford 5-ethoxy-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 3.0 mg, 20.1%).
後処理
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 2 hours
- customThe reaction was quenched
- additionby pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (10 mL)
- extractionextracted with ethyl acetate (3×20 mL)
- washThe combined organic extracts were successively washed with water (10 mL) and brine (10 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by preparative TLC (silica gel, 50% ethyl acetate in hexanes)
出典と根拠
- ORDレコード
- ord-018c36aaeb4640a08fbb2c33188bcdb3
- 出典データセット
- uspto-grants-2003_03
- 特許番号
- US06531598B1
反応ノート
読み込み中…