2-(4-Bromophenyl)-6-methylimidazo[1,2-a]pyridine → 4-(6-Methylimidazo[1,2-a]pyridin-2-yl)benzonitrile

HRID 1590616Notes

Reaction equation

HRID 1590616 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[C:18]([Cu])#[N:19].C(N)CN.O>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8378932-(4-Bromophenyl)-6-methylimidazo[1,2-a]pyridineHCID 12200817Ethylenediamine monohydrateHCID 178418546HCID 178418546, compound

Product 1

HCID 7359124-(6-Methylimidazo[1,2-a]pyridin-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methyl-2-(4'-bromophenyl)imidazo[1,2-a]pyridine (6.0 g) was mixed with 3.0 g of CuCN and 50 ml DMF. The mixture was refluxed for 24 hrs. The hot solution was then poured into a (1:4) ethylenediamine-water mixture (200 ml). Using chloroform, the compound was extracted. The chloroform layer was washed with water, dried and evaporated. The residue was crystallized and recrystallized from ethanol; yield; 3.4 g (69%); mp 225°-226° C.

Workup

  1. temperatureThe mixture was refluxed for 24 hrs
  2. extractionUsing chloroform, the compound was extracted
  3. washThe chloroform layer was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was crystallized
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f3a59b841d974501bf7bbc78456eb120
Source dataset
uspto-grants-1993_04
Patent number
US05204352

Reaction notes

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