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

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridine (4.2 g, 15.4 mmol) in dry tetrahydrofuran (200 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (2.5 M, 9.3 mL, 23.2 mmol) dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (3.45 g, 30.8 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 60% dichloromethane/hexanes) afforded 1-(1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (3.13 g, 53%): LC/MS m/e calcd for C21H24N2O3S [M+H]+ 385.50, observed 384.9.

Provenance & Evidence