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

HRID 517637

Reaktionsgleichung

Reaktionsgleichung von HRID 517637
[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>[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

5

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 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24593copper(I) bromideKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 2-amino-4-bromopyridine (10.0 g, 56.6 mmol), copper (I) bromide (400 mg, 2.70 mmol), 1,10-phenanthroline monohydrate (560 mg, 2.80 mmol) and benzonitrile (130 mL) was heated in a 350 mL 4-necked flask to 130° C. During 45 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below). 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]pyridine (11.6 g, 75%) as a green solid with 100% purity (HPLC area-%, HPLC method see below).

Aufarbeitung

  1. customDuring 45 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below)
  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-ff193dc6e49b406bb65c4f854f806d0b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115130B2

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