Ethyl Acrylate → HCID 66960142, compound

HRID 2247464Notes

Reaction equation

HRID 2247464 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].C([O:18][C:19](=[O:22])[CH:20]=[CH2:21])C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[C:7]([C:6]1[CH:9]=[C:2](/[CH:21]=[CH:20]/[C:19]([OH:22])=[O:18])[CH:3]=[CH:4][C:5]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1)#[N:8]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 669615175-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile

Product 1

HCID 66960142HCID 66960142, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a DMF (10 mL) solution of 5-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile (700 mg) and acrylic acid ethyl ester (362 mg), palladium acetate (31 mg), tri-ortho-tolylphosphine (85 mg) and TEA (2 mL) were added, and the reaction solution was agitated at 80° C. under nitrogen atmosphere overnight. The reaction mixture was concentrated under reduced pressure, water and ethyl acetate were added to the residue, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system), fractions of the object substance were combined, and concentrated under reduced pressure. The obtained substance was dissolved by 5N sodium hydroxide solution (5 mL) and ethanol (30 mL), and the reaction mixture was agitated at 60° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and was made neutral with 5N hydrochloric acid. Insoluble matter consequently deposited was separated by filtering, washed with ether, and 498 mg of the title compound was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water and ethyl acetate
  2. additionwere added to the residue
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system), fractions of the object substance
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe obtained substance was dissolved by 5N sodium hydroxide solution (5 mL) and ethanol (30 mL)
  10. stirringthe reaction mixture was agitated at 60° C. for 3 hours
  11. concentrationThe reaction mixture was concentrated under reduced pressure, water
  12. additionwas added to the residue
  13. customInsoluble matter consequently deposited was separated
  14. filtrationby filtering
  15. washwashed with ether

Sources & evidence

ORD record
ord-9651d9d7e71c4b54ac643cb9a98be651
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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