Water → 5-Bromo-1-(triisopropylsilyl)-1H-indole

HRID 24039

Reaktionsgleichung

Reaktionsgleichung von HRID 24039
C[Si](C)(C)N[Si](C)(C)C.[Li].[Br:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2.[CH:21]([Si:24](Cl)([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])([CH3:23])[CH3:22].O>O1CCCC1>[Br:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:21]([CH3:23])[CH3:22])[CH:16]=[CH:15]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 249055-BromoindoleHCID 139400Triisopropylsilyl chlorideHCID 57426343Lithium bis(trimethylsilyl)amide

Produkt 1

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indoleAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hexamethyldisilazane [1.0 M] (44.7 mL, 44.4 mmol) was added to a solution of 5-bromo-1H-indole (7.30 g, 37.0 mmol) in tetrahydrofuran (50 mL) at room temperature. After stirring for 5 minutes, triisopropylsilyl chloride (8.62 g, 44.4 mmol) was added to reaction mixture and stirred for 30 minutes. Water was added to quench the reaction and the solvent was removed under reduced pressure to give the crude mixture, which was purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate) to give the title compound in 92% yield. 1H NMR (CDCl3) δ 7.74 (d, J=1.8, 1H), 7.36 (d, J=8.8 Hz, 1H), 7.22 (m, 2H), 6.55 (d, J=3.1 Hz, 1H), 1.65 (m, 3H), 1.12 (d, J=7.5 Hz, 18H).

Aufarbeitung

  1. stirringstirred for 30 minutes
  2. customto quench
  3. customthe reaction
  4. customthe solvent was removed under reduced pressure
  5. customto give the crude mixture, which
  6. customwas purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0561702af9fa4419aaedbad71faaa47d
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855722B2

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