Potassium Carbonate → HCID 178450934, compound

HRID 2389292Notes

Reaction equation

HRID 2389292 reaction equation
I[C:2]1[N:3]=[C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:5][CH:6]=1.[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[CH:12]=[CH2:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[C:16]([O:15][C:11](=[O:14])[CH:12]=[CH:13][C:2]1[N:3]=[C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:5][CH:6]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 15458tert-Butyl acrylateHCID 178441780HCID 178441780, compound

Product 1

HCID 178450934HCID 178450934, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-iodo-2-tert-butylimidazole (200 mg, 0.80 mmol) obtained in Step 3 of Example 81, tert-butyl acrylate (240 μL, 1.63 mmol), palladium acetate (18 mg, 0.080 mmol), triphenylphosphine (42 mg, 0.016 mmol), potassium carbonate (133 mg, 0.962 mmol), and DMF (10 mL) was stirred at 100° C. for 3 hours. The mixture was left to cool to room temperature and filtered through Celite. To the filtrate, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20) to give 3-(2-tert-butyl-1H-imidazol-4-yl)acrylic acid tert-butyl ester (51 mg, 0.22 mmol, yield: 26%).

Workup

  1. waitThe mixture was left
  2. temperatureto cool to room temperature
  3. filtrationfiltered through Celite
  4. additionTo the filtrate, an aqueous sodium hydrogen carbonate solution was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-72a36b174c9b4c4a9a346d7b5600caee
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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