1,10-Phenanthroline hydrate → 7-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridine

HRID 517642

Reaktionsgleichung

Reaktionsgleichung von HRID 517642
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.O.N1[C:23]2[C:14](=[CH:15][CH:16]=[C:17]3[C:22]=2N=CC=C3)[CH:13]=CC=1.O=O.[N:26]#N>[Cu]Br.C(#N)C1C=CC=CC=1>[Br:8][C:6]1[CH:5]=[CH:4][N:3]2[N:26]=[C:13]([C:14]3[CH:23]=[CH:22][CH:17]=[CH:16][CH:15]=3)[N:1]=[C:2]2[CH:7]=1

Komponenten

6

Edukt 3

HCID 212261,10-Phenanthroline hydrateHCID 114954NitroxHCID 6932822-Amino-4-bromopyridine

Produkt 1

HCID 677755007-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 7505BenzonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 2-amino-4-bromopyridine (5.00 g, 28.3 mmol), copper (I) bromide (207 mg, 1.44 mmol), 1,10-phenanthroline monohydrate (284 mg, 1.44 mmol) and benzonitrile (60 mL) was heated in a 380-mL autoclave to 130° C. and stirred for 23 h under 20 bar of O2/N2 (5:95). After the autoclave was vented and opened (100% conversion, HPLC method cf. example 1.3), the dark brown reaction suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (40 mL) and dried to yield crude 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (5.12 g, 64%) as a green solid with 97.0% purity (HPLC area-%, HPLC method see example 1.3).

Aufarbeitung

  1. temperaturethe dark brown reaction suspension was then cooled to 0-5° C.
  2. filtrationfiltered
  3. washThe filter cake was washed with TBME (40 mL)
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-03ba9eed6cf648e3940b9cad92af2fb3
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115130B2

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