Triethylamine → HCID 57749238, compound

A mixture of 5-(3-nitrophenoxy)pyridine-2-carboxylic acid (10.4 g, 40.0 mmol), diphenylphosphoryl azide (10.8 mL, 50.0 mmol), triethylamine (6.92 mL, 50.0 mmol) and tert-butanol (200 mL) was stirred at room temperature for 3 hr, and then stirred with heating under reflux for 15 hr. The reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (20 mL) was added to the residue, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (70 mL) was added to the residue, and the mixture was stirred with heating under refluxing conditions for 3 hr. After extraction with ethyl acetate (×3), the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was dried to give the title compound (5.80 g, 63%) as a white solid.

1. stirringstirred
2. temperaturewith heating
3. temperatureunder reflux for 15 hr
4. concentrationThe reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (20 mL)
5. additionwas added to the residue
6. stirringthe mixture was stirred at room temperature for 1 hr
7. concentrationThe reaction mixture was concentrated under reduced pressure, 8N aqueous sodium hydroxide solution (70 mL)
8. additionwas added to the residue
9. stirringthe mixture was stirred
10. temperaturewith heating under refluxing conditions for 3 hr
11. extractionAfter extraction with ethyl acetate (×3)
12. washthe organic layer was washed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltrated
15. concentrationThe filtrate was concentrated under reduced pressure
16. customthe residue was dried

ORD record

ord-1edc16a51c604bff97402b02e5d9217a

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304557B2