反应详情

To a solution of 1-benzenesulfonyl-5-methylthio-1H-indole-2-carboxylic acid methyl ester (370 mg) in ethanol (12 ml), hydrazine monohydrate (0.55 ml) was added at 15 to 30° C. and the mixture was heated under reflux for 13 hours. Further, to the mixture was added hydrazine monohydrate (0.55 ml) and the mixture was heated under reflux for 5 hours. The reaction solution was concentrated under reduced pressure. To the resulting residue was added water, and the insolubles were filtered off and washed with water and ether. To the filtered crude product was added formic acid (9 ml) and the mixture was heated under reflux for 1 hour. The reaction solution was concentrated under reduced pressure. To the resulting residue was added ethyl acetate and the insolubles were filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to obtain 330 mg of the crude product of 1-benzenesulfonyl-5-methylthio-1H-indole-2-carboxylic acid-N′-formylhydrazide. A mixture solution of 509 mg of the crude product thus obtained and phosphorus oxychloride (15 ml) was stirred at 15 to 30° C. for 6 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (ethyl acetate:hexane 1:2) to obtain 265 mg of the desired product.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 13 hours
3. temperaturethe mixture was heated
4. temperatureunder reflux for 5 hours
5. concentrationThe reaction solution was concentrated under reduced pressure
6. additionTo the resulting residue was added water
7. filtrationthe insolubles were filtered off
8. washwashed with water and ether
9. filtrationTo the filtered crude product
10. additionwas added formic acid (9 ml)
11. temperaturethe mixture was heated
12. temperatureunder reflux for 1 hour
13. concentrationThe reaction solution was concentrated under reduced pressure
14. additionTo the resulting residue was added ethyl acetate
15. filtrationthe insolubles were filtered off
16. washwashed with ethyl acetate
17. concentrationThe filtrate was concentrated under reduced pressure
18. customto obtain 330 mg of the crude product of 1-benzenesulfonyl-5-methylthio-1H-indole-2-carboxylic acid-N′-formylhydrazide
19. customA mixture solution of 509 mg of the crude product thus obtained
20. concentrationThe reaction solution was concentrated under reduced pressure
21. customThe resulting residue was separated