反应详情

温度

0 °C

2-Methylsulfonyl-N-[3-phenethyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-yl]benzenesulfonamide can be obtained in the following way: 0.6 g 2-methylsulfonylbenzenesulfonyl chloride is added portionwise to a solution, at a temperature in the region of 0° C. and under argon, of 0.83 g of 5-amino-3-phenethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole in 13 ml of pyridine. The reaction mixture is then stirred for 0.5 hours at a temperature in the region of 0° C. then 2 hours at a temperature in the region of 20° C., and is then diluted with 13 ml of water. After settling out, the aqueous phase is extracted with 3 times 30 ml of ethyl acetate. The organic extracts are pooled, washed with 2 times 15 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 40° C. The residue thus obtained is purified by chromatography under argon pressure (50 kPa), on a cartridge of 70 g of silice (particle size 20-40 μm), eluting successively with pure cyclohexane then with a cyclohexane/ethyl acetate (80/20 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 25° C. 0.56 g of 2-methylsulfonyl-N-[3-phenethyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazol-5-yl]benzenesulfonamide are obtained in the form of a brown-colored paste (Rf=0.32, silica gel thin layer chromatography, eluent: cyclohexane/ethyl acetate (70/30 by volume)).

1. extractionthe aqueous phase is extracted with 3 times 30 ml of ethyl acetate
2. washwashed with 2 times 15 ml of a saturated aqueous sodium chloride solution
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
6. customThe residue thus obtained
7. customis purified by chromatography under argon pressure (50 kPa)
8. washon a cartridge of 70 g of silice (particle size 20-40 μm), eluting successively with pure cyclohexane
9. additionThe fractions containing the expected product
10. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 25° C