Triethylamine → HCID 70019304, compound

HRID 1358901Notes

Reaction equation

HRID 1358901 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](OB(O)O)=[C:10]([F:19])[CH:9]=1.[F:20][C:21]1[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:22]=1[C:23]#[N:24].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=O)C>[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:27]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([F:20])[CH:28]=2)=[C:10]([F:19])[CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 7360294-Bromo-2-fluorobenzonitrileHCID 18179283HCID 18179283, compound

Product 1

HCID 70019304HCID 70019304, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To 300 ml of DMF were added 14 g (54 mmol) of 4-(1,3-dioxolan-2-ylethyl)-2,6-difluorophenylboric acid obtained in Step 2 of Example 1, 10 g (50 mmol) of 2-floro-4-bromobenzonitrile, 20 g (198 mol) of triethyl amine, 0.50 g (2.2 mmol) of palladium acetate, and 0.50 g (3.8 mmol) of triphenylphosphine, and the mixture was refluxed for 7 hours. The solvent was distilled off under reduced pressure. To the residue were added 700 ml of methylene chloride and 300 ml of a 10% aqueous ammonia, and the mixture was stirred. The organic layer was dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography on silica gel (eluting solvent: toluene/ethyl acetate=5/1). The solvent was distilled under reduced pressure and the residue was washed with ethanol and then dried under reduced pressure to afford 11 g (33 mmol) of 1-(1,3-dioxolan-2-ylethyl)-3,5-difluoro-4-(3-fluoro-4-cyanophenyl)benzene.

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionTo the residue were added 700 ml of methylene chloride and 300 ml of a 10% aqueous ammonia
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluting solvent: toluene/ethyl acetate=5/1)
  7. distillationThe solvent was distilled under reduced pressure
  8. washthe residue was washed with ethanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-30cbec06a60c483092d159065199c6c6
Source dataset
uspto-grants-2003_07
Patent number
US06599590B2

Reaction notes

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