反应详情

In a round bottom flask, {5-[(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-6-fluoro-pyridin-2-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (166, 1.15 g, 1.65 mmol) was combined with 50 mL of 1,2-dichloroethane, trifluoroacetic acid (0.635 mL, 8.24 mmol), and triethylsilane (1.32 mL, 8.24 mmol). The reaction was heated at reflux for 20 hours, then concentrated under vacuum. The residue was dissolved in 10 mL of trifluoroacetic acid and stirred at room temperature for 18 hours, then concentrated under vacuum and combined with aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate, water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (167, 403 mg). MS (ESI) [M−H+]−=460.8 and 462.8.

1. temperatureThe reaction was heated
2. temperatureat reflux for 20 hours
3. concentrationconcentrated under vacuum
4. dissolutionThe residue was dissolved in 10 mL of trifluoroacetic acid
5. concentrationconcentrated under vacuum
6. extractionextracted with ethyl acetate
7. washThe organic layer was washed with sodium bicarbonate, water and brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationthe filtrate concentrated under vacuum
11. customThe resulting material was purified by silica gel column chromatography
12. washeluting with ethyl acetate and hexane
13. concentrationconcentrated under vacuum