反应详情

A mixture of 1-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.5 g, 8.68 mmol) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1 M, 9.11 mL, 9.11 mmol) was stirred for 2 h at room temperature. The mixture was poured into brine (15 mL), extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash column chromatography (Qingdao silica gel, 300 mesh, 20% ethyl acetate/hexanes) afforded 5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (600 mg, 48%) as a white solid which was used in the next step without purification: LC/MS m/e calcd for C9H10N2O [M+H]+ 179.26, observed 179.2.

1. extractionextracted with ethyl acetate (2×50 mL)
2. washwashed with a saturated aqueous ammonium chloride solution (3×20 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated in vacuo
5. customPurification by flash column chromatography (Qingdao silica gel, 300 mesh, 20% ethyl acetate/hexanes)