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

HRID 1844437Notes

Reaction equation

HRID 1844437 reaction equation
[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

Participants

5

Reactant 2

HCID 793-CyanopyridineHCID 706222-Amino-5-bromopyridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 212261,10-Phenanthroline hydrateCatalystHCID 24593copper(I) bromideCatalyst

Conditions

Temperature
135 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-e1424ac3a6534a989d871d76ae5747a9
Source dataset
uspto-grants-2015_02
Patent number
US08946427B2

Reaction notes

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