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

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (10.9 g, 39.5 mmol) in dry tetrahydrofuran (200 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (2.5 M, 23 mL, 55.3 mmol) dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (8 g, 71.1 mmol) dropwise. The mixture was stirred at −78° C. for 1 h and quenched with brine. The resulting 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, 25% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol as a white solid (12.5 g, 81.5%): LC/MS m/e calcd for C20H21FN2O3S [M+H]+ 389.46, observed 388.9.

Provenance & Evidence