3-Cyanopyridine → 6-Bromo-2-(pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridine

HRID 588419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588419
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:9](#[N:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1>[Cu]Br.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:16]=[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:8]=2)[CH:7]=1

Komponenten

5

Edukt 2

HCID 793-CyanopyridineHCID 706222-Amino-5-bromopyridine

Produkt 1

HCID 717439846-Bromo-2-(pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 212261,10-Phenanthroline hydrateKatalysatorHCID 24593copper(I) bromideKatalysator

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of 5-bromopyridin-2-amine (2 g, 11.6 mmol), nicotinonitrile (24.1 g, 231 mmol), 1,10-phenanthroline monohydrate (115 mg, 578 μmol) and copper (I) bromide (82.9 mg, 578 μmol) was placed in a 100 ml 2 necked flask and heated to 135° C. Heating was continued while air was bubbled gently through the mixture for 1.5 days. The excess nicotinonitrile was distilled off under reduced pressure and the black residue purified by chromatography (70 g silicagel column using heptane/ethyl acetate 10-100% as eluent). Final evaporation of the solvents afforded 6-bromo-2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine (1.66 g, 52%) as yellow solid. Mp.: 176° C. MS: m/z=275/277 (M+H+).

Aufarbeitung

  1. temperatureHeating
  2. customwas bubbled gently through the mixture for 1.5 days
  3. distillationThe excess nicotinonitrile was distilled off under reduced pressure
  4. customthe black residue purified by chromatography (70 g silicagel column using heptane/ethyl acetate 10-100% as eluent)
  5. customFinal evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-f335f1f102924476b473871767ef172d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227970B2

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