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

HRID 1295178Notes

Reaction equation

HRID 1295178 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-aa371aada629411ab7e3572636d24420
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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