Benzonitrile → HCID 71680411, compound

HRID 1844432Notes

Reaction equation

HRID 1844432 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]=[CH:12][CH:11]=1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]Br>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:16]=[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 7505BenzonitrileHCID 212261,10-Phenanthroline hydrate2×HCID 706222-Amino-5-bromopyridine

Product 1

HCID 71680411HCID 71680411, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst2×

Conditions

Temperature
135 °C

Procedure

A mixture of 5-bromopyridin-2-amine (2 g, 11.6 mmol), benzonitrile (26.2 g, 26.1 ml, 254 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. The mixture was heated to 135° C. while air was bubbled gently through the mixture for 2 days. Another portion of copper (I) bromide (82.9 mg, 578 μmol) and 1,10-phenanthroline monohydrate (115 mg, 578 μmol) was added and bubbling and heating was continued for further 8 hours. The solvent was evaporated. Purification by flash chromatography on a 20 g silicagel column using heptane/ethyl acetate 10-50% as eluent and evaporation of the solvents afforded 6-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (1.19 g, 38%) as light yellow solid. Mp.: 146° C. MS: m/z=274/276 (M+H+).

Workup

  1. customwas bubbled gently through the mixture for 2 days
  2. custombubbling
  3. temperatureheating
  4. customThe solvent was evaporated
  5. customPurification by flash chromatography on a 20 g silicagel column
  6. customevaporation of the solvents

Sources & evidence

ORD record
ord-4211c5510cd34dc4b91ac628f008a1ab
Source dataset
uspto-grants-2015_02
Patent number
US08946427B2

Reaction notes

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