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

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-benzenesulfonyl-5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine (5 g, 15.3 mmol) in dry tetrahydrofuran (100 mL) at −78° C. was added a solution n-butyllithium in n-hexane (1.6 M, 9.2 mL, 23.0 mmol). The mixture was stirred at −78° C. for 15 min and then treated with cyclopentanecarbaldehyde (3.1 g, 27.6 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×150 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, 20% ethyl acetate/hexanes) afforded 1-[1-benzenesulfonyl-5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol (1.4 g, 20.9%): LC/MS m/e calcd for C24H26N2O4S [M+H]+ 439.55, observed 439.0.

Provenance & Evidence