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

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.68 g, 8.43 mmol) in dry tetrahydrofuran (60 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (1.6M, 6.85 mL, 10.96 mmol) dropwise. The mixture was stirred at −78° C. for 10 min and then treated with cyclopentanecarbaldehyde (1.42 g, 12.65 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 (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (3.0 g, 83%) as a white solid: LC/MS m/e calcd for C22H26N2O3S2 [M+H]+ 431.59, observed 431.1.

Provenance & Evidence