HCID 67547686, compound → HCID 67546996, compound

HRID 2356728Notes

Reaction equation

HRID 2356728 reaction equation
Br[C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[Br-].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Zn+])=[CH:23][C:22]=1[F:28]>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[O:6][C:5]([C:7]3[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=3)=[N:4][C:3]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:23][C:22]=1[F:28]

Participants

5

Reactant 2

HCID 67547686HCID 67547686, compoundHCID 178505962HCID 178505962, compound

Product 1

HCID 67546996HCID 67546996, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-bromo-2-(4-fluorophenyl)oxazol-4-carboxylate (600 mg), 0.05M (4-chloro-3-fluorophenyl) zinc bromide (6 ml, tetrahydrofuran solution), and tetrakis-(triphenylphosphine) palladium (231 mg) in tetrahydrofuran (5 ml) was stirred under argon atmosphere at room temperature for 2 hours, followed by refluxing for 40 minutes. The reaction mixture was cooled and concentrated under reduced pressure, and water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent: ethyl acetate:n-hexane=1:8) to obtain ethyl 5-(4-chloro-3-fluoro-phenyl)-2-(4-fluorophenyl)oxazol-4-carboxylate (580 mg) as pale reddish solid.

Workup

  1. temperatureby refluxing for 40 minutes
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was successively washed with 10% hydrochloric acid
  7. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent: ethyl acetate:n-hexane=1:8)

Sources & evidence

ORD record
ord-11c96f3c1e864236bfbdac9c5243afd1
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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