Triethylamine → 1-Phenylsulfonyl-5-trimethylsilylethynylindole

HRID 352768Notes

Reaction equation

HRID 352768 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:46][Si:47]([C:50]#[CH:51])([CH3:49])[CH3:48]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C.CN(C)C=O>[C:14]1([S:11]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:51]#[C:50][Si:47]([CH3:49])([CH3:48])[CH3:46])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indole

Product 1

HCID 227101661-Phenylsulfonyl-5-trimethylsilylethynylindole

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In tetrahydrofuran (7.00 ml), 5-bromo-1-phenylsulfonylindole (1.50 g) and triphenylphosphine (351 mg) were dissolved. Triethylamine (20 ml), N,N-dimethylformamide (7.00 ml), trimethylsilylacetylene (945 up) and palladium acetate (100 mg) were added to the resulting solution at room temperature, followed by heating under reflux for 5 hours. After the reaction mixture was allowed to cool down to room temperature, ethyl acetate and water were added to the reaction mixture to separate the organic layer. The resulting organic layer was dried over anhydrous sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=20:1 to 10:1), whereby the title compound (935 mg, 59%) was obtained as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customto separate the organic layer
  4. dry with materialThe resulting organic layer was dried 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 (hexane:ethyl acetate=20:1 to 10:1), whereby the title compound (935 mg, 59%)
  8. customwas obtained as a white solid

Sources & evidence

ORD record
ord-fcfe8dd1bb1e435ab49ee672503ac59c
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…