Trimethyl orthoformate → HCID 67155774, compound

Participants

Reaction Steps

A round-bottom flask was charged with 5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (0.30 g, 0.91 mmol), dimethylamine hydrochloride salt (0.10 g, 1.27 mmol), trimethoxymethane (0.99 mL, 9.1 mmol), sodium triacetoxyborohydride (0.25 g, 1.18 mmol), sodium acetate (0.10 g, 1.27 mmol) and 1,2-dichloroethane (9.0 mL). The mixture was stirred at room temperature for 24 hours, after which saturated aqueous sodium bicarbonate was added, then dichloromethane. The layers were separated. The aqueous layer was extracted twice with dichloromethane. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography to afford N,N-dimethyl-1-(5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanamine (0.16 g, 49%).

Provenance & Evidence