Water → HCID 67155777, compound

Participants

Reaction Conditions

Reaction Steps

Lithium diisopropylamide (19.4 mL, 35.0 mmol, 1.8M in heptane/THF/ethylbenzene) was added to a solution of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (4.50 g, 17.4 mmol) in THF (100 mL) at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes, and then acetic anhydride (6.6 mL, 69.7 mmol) was added. The reaction mixture was warmed up to room temperature and stirred for 40 minutes. The reaction mixture was treated with water and dichloromethane, and the layers were separated. The aqueous layer was extracted once with dichloromethane. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford 1-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)ethanone (2.15 g, 41%).

Provenance & Evidence