Triethylamine → 1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-4-phenyl-butan-1-one

HRID 1512612Notes

Reaction equation

HRID 1512612 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([OH:18])[CH2:15][CH:16]=[CH2:17])=[CH:4][CH:3]=1.I[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 665813481-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]but-3-en-1-ol

Product 1

HCID 665772561-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-4-phenyl-butan-1-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-but-3-en-1-ol (1.76 g, 5.69 mmol), iodobenzene (0.638 mL, 5.69 mmol), and triethylamine (1.59 mL, 11.38 mmol) were dissolved in ACN (17 mL) and the solution was purged with bubbling N2 (g). Palladium(II) acetate (0.064 g, 0.28 mmol) was added, the reaction vessel was sealed, and the reaction was heated to 85° C. overnight. After cooling, the reaction was submitted to standard aqueous workup then purified on silica gel (0-30% EtOAc in hexanes) to give a separable mixture of two compounds, one of which was the title compound.

Workup

  1. customthe solution was purged with bubbling N2 (g)
  2. customthe reaction vessel was sealed
  3. temperatureAfter cooling
  4. customthen purified on silica gel (0-30% EtOAc in hexanes)
  5. customto give
  6. additiona separable mixture of two compounds, one of which

Sources & evidence

ORD record
ord-5c59c57933bd4e08a0cd07cb8261b6ab
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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