Triethylamine → 1-Phenylsulfonyl-5-trimethylsilylethynylindole

HRID 352768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352768
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

Komponenten

10

Edukt 4

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

Produkt 1

HCID 227101661-Phenylsulfonyl-5-trimethylsilylethynylindole

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fcfe8dd1bb1e435ab49ee672503ac59c
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747023B1

Notizen zur Reaktion

Wird geladen…