Hexane → 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol

関与物質

反応条件

反応手順

To a suspension of 1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (1.1 g, 3.99 mmol) in dry tetrahydrofuran (30 mL) at −78° C. at was added n-butyllithium in n-hexane (1.6 M, 2.74 mL, 4.38 mmol) dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (0.67 g, 5.99 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 50% dichloromethane/hexanes) afforded 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (1.55 g, 100%): LC/MS m/e calcd for C20H21FN2O3S [M+H]+ 389.46, observed 389.2.

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