Benzonitrile → 7-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridine

HRID 517635

Reaktionsgleichung

Reaktionsgleichung von HRID 517635
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:24](#[N:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cu]Br.[I-].[Zn+2].[I-]>[Br:8][C:6]1[CH:5]=[CH:4][N:3]2[N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:1]=[C:2]2[CH:7]=1

Komponenten

6

Edukt 3

HCID 7505BenzonitrileHCID 212261,10-Phenanthroline hydrateHCID 6932822-Amino-4-bromopyridine

Produkt 1

HCID 677755007-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 9883512zinc(II)iodideKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 2-amino-4-bromopyridine (5.00 g, 28.9 mmol), copper (I) bromide (207 mg, 1.44 mmol), 1,10-phenanthroline monohydrate (289 mg, 1.44 mmol), zinc iodide (923 mg, 2.89 mmol) and benzonitrile (125 mL) was heated in a 250-mL 3-necked flask to 130° C. During 23 h a gentle flow of air was bubbled through the reaction mixture (93% conversion, HPLC method cf. example 1.3). The dark brown suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (50 mL) and dried to yield crude 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyrdine (5.36 g, 51%) as a green solid with 76.0% purity (HPLC area-%, HPLC method cf. example 1.3). Major by-product: 7-Iodo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (13.0%).

Aufarbeitung

  1. customDuring 23 h a gentle flow of air was bubbled through the reaction mixture (93% conversion, HPLC method cf. example 1.3)
  2. temperatureThe dark brown suspension was then cooled to 0-5° C.
  3. filtrationfiltered
  4. washThe filter cake was washed with TBME (50 mL)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f665791c2cf444268564babecf762f92
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115130B2

Verknüpfte Notizen

Wird geladen…