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

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To a suspension of 1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (2.0 g, 7.25 mmol) in dry tetrahydrofuran (150 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (1.6 M, 6.8 mL, 10.9 mmol) dropwise. The mixture was stirred at −78° C. for 30 min and then treated with cyclopentanecarbaldehyde (1.5 g, 13.04 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, 15% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol as a colorless oil (2.1 g, 74%): LC/MS m/e calcd for C20H21FN2O3S [M+H]+ 389.46, observed 389.0.

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