反应详情

温度

-78 °C

To a solution of 1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 10, 2.5 g, 8.68 mmol) in dry tetrahydrofuran (40 mL) at −78° C. was added freshly prepared lithium diisopropylamide [prepared by adding 1.6 M n-butyllithium in n-hexane (8.13 mL, 13.0 mmol) to a 0° C. solution of diisopropylamine (13.7 mmol, 1.96 mL) in dry tetrahydrofuran (20 mL)] dropwise. The mixture was stirred at −78° C. for 5 min and then cyclopentanecarbaldehyde (13.0 mmol, 1.46 g) was added dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 20% ethyl acetate/hexanes) afforded 1-(-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol (2.3 g, 68%) as a white solid: LC/MS m/e calcd for C21H24N2O4S [M+H]+ 401.50, observed 401.0.

1. customprepared
2. stirringThe resulting mixture was stirred at −78° C. for 1 h
3. customquenched with brine
4. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
5. washwashed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo
8. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 20% ethyl acetate/hexanes)