Reaktion #460677

Reaktionsgleichung

acid 12

3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl] propionic acid

Et3N

diphenylphosphoryl azide

→

2-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-ethyl amine

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated to 70° C. for 1.5 hours
2. 2
   Temperaturcooled
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.ADDITIONwas added
5. 5
   Temperaturthe reaction mixture was heated
6. 6
   Temperaturto reflux for 2 hours
7. 7
   Temperaturcooled
8. 8
   workup.ADDITIONdiluted to 50 ml with EtOAc
9. 9
   WaschenThe organic solution was washed with a 0.25N NaOH solution
10. 10
    Extraktionextracted with 1N HCl
11. 11
    Extraktionextracted with EtOAc
12. 12
    Sonstigedried
13. 13
    Filtrationfiltered
14. 14
    Einengenconcentrated in vacuo
15. 15
    SonstigeCrystallization from Et2O afforded pure 42 (0.62 g, 68%) as a light yellow crystalline solid, mp=95°-97°

Vorschrift

To a solution of the acid 12 (1.0 g, 2.8 mM) in benzene (25 ml) was added Et3N (0.39 ml, 2.8 mM) and diphenylphosphoryl azide (0.60 ml, 2.8 mM). After stirring overnight at room temperature, the reaction mixture was heated to 70° C. for 1.5 hours, cooled and concentrated in vacuo. Dioxane (2 ml), followed by a solution of concentrated HCl (0.3 ml) in dioxane (2 ml) was added, and the reaction mixture was heated to reflux for 2 hours, cooled and diluted to 50 ml with EtOAc. The organic solution was washed with a 0.25N NaOH solution, and extracted with 1N HCl. The extracts were combined, basified with 5N NaOH, and extracted with EtOAc, dried, filtered and concentrated in vacuo. Crystallization from Et2O afforded pure 42 (0.62 g, 68%) as a light yellow crystalline solid, mp=95°-97°. MS, m/e 327 (M+).

Quelle