Proton sponge → HCID 67155995, compound

Participants

Reaction Steps

N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine (0.212 g, 0.99 mmol) and trimethyloxonium tetrafluoroborate (0.146 g, 0.99 mmol) were added to a solution of (5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol (0.11 g, 0.33 mmol) in DCM (3.3 mL). The reaction mixture was stirred at room temperature for 1 hour. It was then treated with saturated aqueous NaHCO3, and the layers were separated. The aqueous layer was extracted with DCM. 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-(methoxymethyl)-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.11 g, 96%).

Provenance & Evidence