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

Temperature

-10 °C

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%).

1. temperatureThe mixture was warmed up
2. stirringstirred at room temperature for 1 hour
3. concentrationconcentrated to half volume
4. extractionextracted with dichlormethane
5. washThe combined organic layer was washed with water, brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-7fac389a0b834e12b311ec61014980f3

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576082B2