Diisopropylamine → HCID 67229605, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-carbamic acid tert-butyl ester (3.48 g, 9.33 mmol) in dry tetrahydrofuran (100 mL) at −78° C. was added freshly prepared lithium diisopropylamide [prepared by adding 1.6 M n-butyllithium in n-hexane (17.5 mL, 28 mmol) to a 0° C. solution of diisopropylamine (2.83 g, 28 mmol) in dry tetrahydrofuran (40 mL)] dropwise. The mixture was stirred at −78° C. for 5 min and then treated with cyclopentanecarbaldehyde (1.57 g, 14 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 (QingDao silica gel, 200-300 mesh, 25% ethyl acetate/hexanes) afforded [1-benzenesulfonyl-2-(2-cyclopentyl-1-hydroxy-ethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid tert-butyl ester as a white solid (0.57 g, 44%): LC/MS m/e calcd for C25H31N3O5S [M+H]+ 486.61, observed 486.0.

Provenance & Evidence