Benzene → 7-Bromo-2-tert-butyl-6-(2-furyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17269Notes

Reaction equation

HRID 17269 reaction equation
[CH:1]1C=C[CH:4]=[CH:3][CH:2]=1.[Br:7][C:8]1[C:9](I)=[C:10]([CH3:23])[C:11]([C:21]#[N:22])=[C:12]2[C:16]=1[O:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[N:13]2.[OH2:25]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:7][C:8]1[C:9]([C:1]2[O:25][CH:4]=[CH:3][CH:2]=2)=[C:10]([CH3:23])[C:11]([C:21]#[N:22])=[C:12]2[C:16]=1[O:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[N:13]2

Participants

5

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 685859347-Bromo-2-tert-butyl-6-iodo-5-methyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685843857-Bromo-2-tert-butyl-6-(2-furyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

Bis(triphenylphosphine)palladium(II) chloride (0.5 mg, 0.72 μmol) was added to a benzene (1.0 ml) solution of 7-bromo-2-tert-butyl-6-iodo-5-methyl-1,3-benzoxazole-4-carbonitrile (I-8) (30 mg, 71.6 μmol), (2-tri-n-butylstannyl)furan (23.7 μl, 75.2 μmol), followed by refluxing overnight. After cooling, water (30 ml) was added, the product was extracted with ethyl acetate (30 ml×2), the organic layer was washed with saturated brine (30 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (h-hexane:ethyl acetate=8:1) to obtain the entitled compound (19 mg) as a colorless solid.

Workup

  1. temperatureby refluxing overnight
  2. temperatureAfter cooling
  3. extractionthe product was extracted with ethyl acetate (30 ml×2)
  4. washthe organic layer was washed with saturated brine (30 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (h-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-3117ae17a81f442f87d7a6710e8bfb9f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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