HCID 178458286, compound → HCID 178458287, compound

HRID 1023881Notes

Reaction equation

HRID 1023881 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](=[CH2:24])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:20]=[CH:21][NH:22][CH:23]=2)=[CH:2]1>CO.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]([CH3:24])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:20]=[CH:21][NH:22][CH:23]=2)=[CH:2]1

Participants

4

Reactant 1

HCID 178458286HCID 178458286, compound

Product 1

HCID 178458287HCID 178458287, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(2-((2-(benzofuran-3-yl)allyl)oxy)phenyl)-1H-imidazole (0.126 mmol) in MeOH (3 mL) at room temperature was added 10% Pd/C (0.019 mmol) and the mixture was flushed with hydrogen gas after evacuating under vacuum. After stirring overnight the solution was filtered through a celite bed and the solvent was evaporated under reduced pressure to afford the crude product. Chromatographic purification afforded the final product. Yield 75%. 1H NMR: 1.55 (d, 3H, J=5.22 Hz), 3.60 (m, 1H), 4.36 (m, 2H), 7.01 (t, 2H J=5.97 Hz), 7.19-7.36 (m, 5H), 7.38 (s, 1H), 7.53 (d, 1H, J=6.09 Hz), 7.58 (s, 1H), 7.64 (d, 1H, J=5.76 Hz), 7.75 (d, 1H, J=5.01 Hz)

Workup

  1. customthe mixture was flushed with hydrogen gas
  2. customafter evacuating under vacuum
  3. filtrationwas filtered through a celite bed
  4. customthe solvent was evaporated under reduced pressure
  5. customto afford the crude product
  6. customChromatographic purification

Sources & evidence

ORD record
ord-c66479f6219443ccbaba3699fb67fb64
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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