tert-Butanol → Methyl 4-bromo-6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

Participants

Reaction Steps

To a mixture of 4.62 g of 4-bromo-6-(methoxycarbonyl)pyridine-2-carboxylic acid, 2.97 ml of triethylamine, 25 ml of t-butanol and 70 ml of 1,4-dioxane was added 4.59 ml of diphenylphosphoryl azide at room temperature. The reaction mixture was heated under reflux for 3 hours and cooled to room temperature. Water was added thereto and the resulting mixture was extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound.

Provenance & Evidence