2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Bromoimidazo[1,2-a]pyridine-3-carbonitrile

HRID 1792459Notes

Reaction equation

HRID 1792459 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]([C:11]#[N:12])[CH2:9][N:10]=2)[CH:7]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 220317966-Bromo-2,3-dihydroimidazo[1,2-a]pyridine-3-carbonitrile

Product 1

HCID 220310786-Bromoimidazo[1,2-a]pyridine-3-carbonitrileYield 85.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Method 1) 3.83 g of 6-bromo-2,3-dihydroimidazo[1,2-a]pyridine-3-carbonitrile synthesized in Production Example 242 was dissolved in 34 mL 1,4-dioxane, and the solution together with 4.3 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was heated at 90° C. for 2 hours. The reaction solution was diluted with ethyl acetate, insolubles were filtered off with Celite, and the filtrate was washed with an aqueous saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate and filtered through NH silica gel. The solvent was removed, whereby 3.24 g of the title compound (brown solid) was obtained.

Workup

  1. filtrationwere filtered off with Celite
  2. washthe filtrate was washed with an aqueous saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered through NH silica gel
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-b62610f5636e4d9282ac7f4af0117a3c
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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