Triethylamine → Methyl 5-(azidocarbonyl)pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of pyridine-2,5-dicarboxylic acid-2-methyl ester (0.5 g, 2.76 mmol)) (from Example 83a supra) at −10° C. in acetone (9.16 mL) was added triethylamine (0.385 mL, 2.76 mmol) (Aldrich), followed by the addition of ethyl chloroformate (0.265 mL, 2.76 mmol). (Aldrich). After the mixture was stirred at −10° C. for 30 minutes, an aqueous solution of sodium azide (0.53 g, 8.28 mmol) in water (10 mL) was added. The mixture was warmed up and stirred at room temperature for 1 hour, then concentrated to half volume, extracted with dichlormethane. The combined organic layer was washed with water, brine, dried over MgSO4 and concentrated to give 5-azidocarbonyl-pyridine-2-carboxylic acid methyl ester as a white solid (Yield 0.47 g, 83%).

Provenance & Evidence