Diisopropylamine → HCID 67229243, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-benzenesulfonyl-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (3 g, 8.06 mmol) in dry tetrahydrofuran (40 mL) at −78° C. was added freshly prepared lithium diisopropylamide [prepared by adding 1.6 M n-butyllithium in n-hexane (8.1 mL, 13.0 mmol) to a 0° C. solution of diisopropylamine (2 mL, 13.8 mmol) in dry tetrahydrofuran (20 mL)] dropwise. The mixture was stirred at −78° C. for 5 min and then cyclopentanecarbaldehyde (1.35 g, 13.0 mmol) was added 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, 25% ethyl acetate/hexanes) afforded 1-[1-benzenesulfonyl-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol as a light yellow solid (850 mg, 22%): LC/MS m/e calcd for C26H32N2O5S [M+H]+ 485.62, observed 485.1.

Provenance & Evidence