Triethylamine → HCID 22710641, compound

HRID 352795Notes

Reaction equation

HRID 352795 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>O1CCCC1.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH3:37][Si:38]([C:41]#[C:42][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1)([CH3:40])[CH3:39]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 127444006-Bromo-benzo[b]thiophene

Product 1

HCID 22710641HCID 22710641, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (15 ml) was dissolved 6-bromobenzo[b]thiophene (2.13 g), followed by the addition of triphenylphosphine (787 mg), triethylamine (40 ml), N,N-dimethylformamide (15 ml), trimethylsilylacetylene (1.47 g) and palladium acetate (225 mg). The resulting mixture was refluxed for 5 hours. After the reaction mixture was allowed to cool down, it was diluted with methylene chloride (150 ml). The diluted mixture was washed with water (twice) and saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (only hexane), whereby the title compound (1.38 g) was obtained.

Workup

  1. temperatureThe resulting mixture was refluxed for 5 hours
  2. temperatureto cool down
  3. washThe diluted mixture was washed with water (twice) and saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (only hexane), whereby the title compound (1.38 g)
  8. customwas obtained

Sources & evidence

ORD record
ord-20ad28c076d24fa792f2a1a7e88a5255
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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