Diisopropylamine → HCID 67228038, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-benzenesulfonyl-6-methoxy-1H-pyrrolo[2,3-b]pyridine (2.0 g, 6.74 mmol) in dry tetrahydrofuran (60 mL) at −78° C. was added freshly prepared lithium diisopropylamide [prepared by adding 1.6 M n-butyllithium in n-hexane (6.6 mL, 10.42 mmol) to a 0° C. solution of diisopropylamine (1.12 g, 11.1 mmol) in dry tetrahydrofuran (20 mL)] dropwise. The mixture was stirred at −78° C. for 20 min and then treated with cyclopentanecarbaldehyde (1.56 g, 13.8 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×100 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, 25% ethyl acetate/hexanes) afforded 1-(-benzenesulfonyl-6-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol as a white solid (2.54 g, 91%): LC/MS m/e calcd for C21H24N2O4S [M+H]+ 401.50, observed 401.2.

Provenance & Evidence