反应详情

温度

20 °C

2-Methylsulfonyl-N-(3-phenethyl-1H-indazol-5-yl)benzenesulfonamide can be obtained in the following way: 5.6 ml of an aqueous 5N hydrochloric acid solution are added dropwise to a suspension of 0.56 g of 2-methylsulfonyl-N-[3-phenethyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-yl]benzenesulfonamide in 17 ml of absolute ethanol. The reaction mixture is then refluxed for 30 minutes and then cooled to a temperature in the region of 20° C. 6.8 ml of an aqueous 5N sodium hydroxide solution are then added and the mixture is stirred. The mixture is then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. and the residue is taken up in a mixture of 35 ml of ethyl acetate and of 50 ml of water. After settling out, the aqueous phase is extracted with 2 times 30 ml of ethyl acetate. The organic extracts are pooled, washed with 2 times 20 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C. The residue thus obtained is purified by chromatography under argon pressure (50 kPa) on a column of 75 g of silica (particle size 40-63 μm), eluting with a dichloromethane/methanol (98/2 by volume) mixture. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C. The residue thus obtained is repurified by chromatography under argon pressure (50 kPa), on a column of silica (particle size 40-63 μm), eluting with a cyclohexane/ethyl acetate (70/30 by volume) mixture. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C. The residue thus obtained is taken up in 15 ml of diisopropyl ether, triturated, filtered and then dried. 130 mg of 2-methylsulfonyl-N-(3-phenethyl-1H-indazol-5-yl)benzenesulfonamide are thus obtained in the form of a white solid melting at 192° C. (CI mass analysis: m/z 456 (M+H)+).

1. temperatureThe reaction mixture is then refluxed for 30 minutes
2. concentrationThe mixture is then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C.
3. additionthe residue is taken up in a mixture of 35 ml of ethyl acetate and of 50 ml of water
4. extractionthe aqueous phase is extracted with 2 times 30 ml of ethyl acetate
5. washwashed with 2 times 20 ml of a saturated aqueous sodium chloride solution
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C
9. customThe residue thus obtained
10. customis purified by chromatography under argon pressure (50 kPa) on a column of 75 g of silica (particle size 40-63 μm)
11. washeluting with a dichloromethane/methanol (98/2 by volume) mixture
12. additionThe fractions containing the expected product
13. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C
14. customThe residue thus obtained
15. customis repurified by chromatography under argon pressure (50 kPa)
16. washon a column of silica (particle size 40-63 μm), eluting with a cyclohexane/ethyl acetate (70/30 by volume) mixture
17. additionThe fractions containing the expected product
18. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C
19. customThe residue thus obtained
20. customtriturated
21. filtrationfiltered
22. customdried