Tetrahydrofuran → 5-methyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

A mixture of 1-(tert-butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine (7.92 g, 32.2 mmol) and a solution tetrabutylammonium fluoride in tetrahydrofuran (1 M, 161 mL, 161 mmol) was stirred for 2 h at room temperature. The mixture was poured into brine (50 mL), extracted with ethyl acetate (2×200 mL), washed with a saturated aqueous ammonium chloride solution (3×60 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by a flash column chromatography (Qingdao silica gel, 300 mesh, 20% ethyl acetate/hexanes) afforded 5-methyl-1H-pyrrolo[2,3-b]pyridine (3.5 g, 82%) as a white solid: LC/MS m/e calcd for C8H8N2 [M+H]+ 133.17, observed 133.0.

Provenance & Evidence