反应详情

To a solution of 6-(methylthio)-1H-indole (1 g, 6.13 mmol), NaOH (4.90 g, 122.6 mmol) and Bu4NHSO4 (207.8 mg, 0.613 mmol) in dichloromethane (20 mL) was added benzenesulfonyl chloride (1.29 g, 7.36 mmol). The reaction mixture was stirred at rt overnight. The mixture was quenched with water (30 mL) and extracted with dichloromethane (30 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography on silica gel eluted with PE/EtOAc 10:1 to afford 6-(methylthio)-1-(phenylsulfonyl)-1H-indole (1.1 g, 59.18% yield) as a white solid. LC-MS MS (ESI) m/z 304.0 [M+H]+. 1H NMR (CDCl3 400 MHz): δ 7.93-7.75 (m, 3H), 7.58-7.41 (m, 5H), 7.17 (dd, J1=8.0 Hz, J2=1.6 Hz, 1H), 6.63-6.60 (m, 1H), 2.53 (s, 3H).

1. customThe mixture was quenched with water (30 mL)
2. extractionextracted with dichloromethane (30 mL×3)
3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. custompurified by column chromatography on silica gel
7. washeluted with PE/EtOAc 10:1