Iodoethane → HCID 852077, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.03 mL, 3.25 mmol, 1.6M in hexanes) was added to a solution of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.60 g, 2.32 mmol) in THF (9.0 mL) at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes, and then iodoethane (0.557 mL, 6.97 mmol) was added. The reaction mixture was warmed up to 0° C. and stirred for 2 hours, after which more iodoethane (0.278 mL, 3.48 mmol) was added. The reaction mixture was warmed up to room temperature and stirred overnight. Saturated aqueous ammonium chloride and ethyl acetate were then added, and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford 2-ethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.25 g, 23% yield).

Provenance & Evidence