反应详情

温度

0 °C

Into a 100 ni 3-necked round bottom flask was placed tetrahydrofuran (50 mL). To the above was added NaH (2.19 g, 54.75 mmol) in several batches, while cooling to a temperature of 0° C. This was followed by the addition of a solution of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2 g, 13.70 mmol) in tetrahydrofuran (400 mL), which was added dropwise with stirring, while cooling to a temperature of 0° C. The resulting solution was allowed to react, with stirring, for 30 minutes while the temperature was maintained at room temperature. This was followed by the addition of a solution of benzenesulfonyl chloride (3.63 g, 20.55 mmol) in tetrahydrofuran (50 mL), which was added dropwise with stirring, while cooling to a temperature of 0° C. The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at room temperature. The reaction mixture was then quenched by the adding of H2O. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The residue was dissolved in 300 mL of ethyl acetate. The resulting mixture was washed two times with 200 mL of brine and the organic layers combined. The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The resulting mixture was washed with ethyl acetate/petroleum ether=1:40. This resulted in 3.4 g (82%) of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a light yellow solid.

1. additionwas added dropwise
2. temperaturewhile cooling to a temperature of 0° C
3. customto react
4. stirringwith stirring, for 30 minutes while the temperature
5. temperaturewas maintained at room temperature
6. additionwas added dropwise
7. stirringwith stirring
8. temperaturewhile cooling to a temperature of 0° C
9. customto react
10. stirringwith stirring, for 3 hours while the temperature
11. temperaturewas maintained at room temperature
12. customThe reaction mixture was then quenched by the
13. additionadding of H2O
14. concentrationThe mixture was concentrated by evaporation under vacuum
15. customa rotary evaporator
16. dissolutionThe residue was dissolved in 300 mL of ethyl acetate
17. washThe resulting mixture was washed two times with 200 mL of brine
18. dry with materialThe mixture was dried over Na2SO4
19. concentrationconcentrated by evaporation under vacuum
20. customa rotary evaporator
21. washThe resulting mixture was washed with ethyl acetate/petroleum ether=1:40
22. customThis resulted in 3.4 g (82%) of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a light yellow solid