Triethylamine → HCID 70019004, compound

HRID 1358900Notes

Reaction equation

HRID 1358900 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11](B(O)O)=[C:10]([F:18])[CH:9]=1.Br[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[C:10]([F:18])[CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 12162Benzonitrile, 4-bromo-HCID 18179286HCID 18179286, compound

Product 1

HCID 70019004HCID 70019004, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To 150 ml of N,N-dimethyl formamide (hereinafter abbreviated as “DMF”) were added 7.0 g (27 mmol) of 4-(1,3-dioxolan-2-ylethyl)-2,6-diflurophenyl boronic acid obtained in Step 2, 5.0 g (27 mmol) of 4-bromobenzonitrile, 10 g (99 mmol) of triethyl amine, 0.20 g (0.89 mmol) of palladium acetate and 0.50 g (1.9 mmol) of triphenylphosphine and the mixture was refluxed for 4 hours. The solvent was distilled off under reduced pressure. To the residue of this distillation were added 500 ml of methylene chloride and 250 ml of a 10% aqueous ammonia and the mixture was stirred. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (eluting solvent: toluene/ethyl acetate=5/1) and then the solvent was distilled off under reduced pressure. The residue thus obtained was washed with ethanol and then dried under reduced pressure to afford 4.4 g (14 mmol) of 1-(1,3-dioxolan-2-ylethyl)-3,5-difluoro-4-(4-cyanophenyl)benzene. (Yield: 52%)

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. distillationTo the residue of this distillation
  4. additionwere added 500 ml of methylene chloride and 250 ml of a 10% aqueous ammonia
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluting solvent: toluene/ethyl acetate=5/1)
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained
  10. washwas washed with ethanol
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-0e402d3d356c4d2482b75dd401a1b367
Source dataset
uspto-grants-2003_07
Patent number
US06599590B2

Reaction notes

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