Acrylonitrile → HCID 66839356, compound

HRID 546764Notes

Reaction equation

HRID 546764 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]2)=[N:6][CH:7]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)C(C)C)(C)C.[C:47](#[N:50])[CH:48]=[CH2:49]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH3:15][O:14][C:4]1[CH:3]=[C:2](/[CH:49]=[CH:48]/[C:47]#[N:50])[CH:7]=[N:6][C:5]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1

Participants

7

Reactant 4

HCID 7855AcrylonitrileHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 66618923HCID 66618923, compound

Product 1

HCID 66839356HCID 66839356, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-bromo-3-methoxy-2-(4-methyl-1H-imidazol-1-yl)pyridine (3.8 g), tris(dibenzylideneacetone)dipalladium (650 mg), tri-o-tolylphosphine (433 mg), N,N-diisopropylethylamine (4.86 mL), DMF (14.1 mL) and acrylonitrile (2.82 mL) was stirred in a nitrogen atmosphere at 110° C. for five hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. The residue was diluted with ethyl acetate and then filtered through celite, and the filtrate was washed with water. The organic layer was concentrated under reduced pressure, and the precipitated crystals were hot dissolved in ethyl acetate. After leaving to cool to room temperature, the precipitated crystals were collected by filtration and air-dried to obtain 1.79 g of the title compound. The filtrate was concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (heptane-ethyl acetate system) and then recrystallized from ethyl acetate to obtain 0.312 g of the title compound. The property value of the compound is as follows.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. filtrationfiltered through celite
  6. washthe filtrate was washed with water
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. dissolutionthe precipitated crystals were hot dissolved in ethyl acetate
  9. customAfter leaving
  10. temperatureto cool to room temperature
  11. filtrationthe precipitated crystals were collected by filtration
  12. customair-dried

Sources & evidence

ORD record
ord-24c4ecd1321248dd9d85cad4019390dc
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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