反应详情

A solution of iodine monochloride (2.83 g, 17.4 mmol) in MeOH (25 mL) was added over approximately 0.5 h via pressure equalizing addition funnel to a vigorously stirred mixture of methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate (6.00 g, 13.4 mmol) and silver tetrafluoroborate (3.39 g, 17.4 mmol) in MeOH/THF (1:2; 75 mL) at 0° C. After an additional 0.5 h, the reaction was quenched with 1M Na2S2O3, warmed to room temperature and filtered through celite® washing copiously with ethyl acetate. The filtrate was concentrated under reduced pressure, poured into 1M Na2S2O3 and extracted with ethyl acetate (×3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25% ethyl acetate/hexanes as eluent) to give the title compound as a colourless solid (5.54 g).

1. additionaddition funnel
2. customthe reaction was quenched with 1M Na2S2O3
3. filtrationfiltered through celite®
4. washwashing copiously with ethyl acetate
5. concentrationThe filtrate was concentrated under reduced pressure
6. additionpoured into 1M Na2S2O3
7. extractionextracted with ethyl acetate (×3)
8. extractionThe combined organic extract
9. washwas washed with brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated in vacuo
12. customThe residue was purified by flash chromatography on silica gel (25% ethyl acetate/hexanes as eluent)