1,2-Dichloroethane → N-Methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

Participants

Reaction Steps

To a solution of 7-azaindole-3-carboxylic acid (324 mg, 2.00 mmol) in dioxane (10 mL) was added HOAt (300 mg, 2.20 mmol), N,O-Dimethylhydroxylamine hydrochloride (214 mg, 2.00 mmol) and EDC (422 mg, 2.20 mmol). The mixture was stirred at rt for 15 minutes then DIPEA (853 mg, 6.60 mmol) added slowly over 5 minutes. The reaction was then stirred at rt for an additional 18 hrs. The reaction was then poured into 25% ammonium chloride solution (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were dried over magnesium sulfate, filtered and concentrated to a brown oil. This oil was purified via column chromatography (SiO2, EtOAc) to afford the title compound as a viscous clear oil which solidified on standing. Yield=86%

Provenance & Evidence