tert-Butanol → HCID 67353414, compound

Participants

Reaction Steps

In a 500 mL pear flask was added 1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (1G, assumed 30.4 mmol) in dioxane (90 ml) and t-butanol (90 ml) to give a brown suspension. To this was then added triethylamine (5.5 ml, 40 mmol) and the mixture was then heated to 85° C. After 7 hours, the reaction did not change much from the 25% conversion achieved in the first two hours. An additional 4.3 ml of diphenylphosphoryl azide (0.65 eq.) was added the next morning and after 5 hours, the reaction has progressed significantly. Brine was added and the mixture was extracted twice with ethyl acetate. Combined organic layers were dried over MgSO4, filtered and concentrated. Crude product was purified by column chromatography (SiO2, eluting with a gradient of 20-30% EtOAc/hexanes) to give tert-butyl 1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (1H, 3.6 g, 45%).

Provenance & Evidence