反应详情

温度

-78 °C

To a suspension of 1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridine (0.45 g, 1.56 mmol) in dry tetrahydrofuran (20 mL) at −78° C. was added freshly prepared lithium diisopropylamide [prepared by adding 1.6 M n-butyllithium in n-hexane (1.5 mL, 2.34 mmol) to a 0° C. solution of diisopropylamine (0.35 mL, 2.48 mmol) in dry tetrahydrofuran (10 mL)] dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclohexanecarbaldehyde (353.8 mg, 2.81 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and then 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-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclohexyl-ethanol (240 mg, 37.2%) as a white solid: LC/MS m/e calcd for C22H26N2O4S [M+H]+ 415.53, observed 415.3.

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)