Sodium hydride → 4-bromo-1-(triisopropylsilyl)-1H-indole

HRID 8314

Reaction equation

HRID 8314 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>C(Cl)Cl.CN(C=O)C>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 6764944-Bromoindole

Product 1

HCID 27955734-bromo-1-(triisopropylsilyl)-1H-indoleYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The NaH 60% dispersion in oil (0.94 g, 23.4 mmol) was added to a solution of 4-bromoindole (3.07 g, 15.6 mmol) and triisopropylsilyl chloride (3.62 g, 18.8 mmol) in CH2Cl2 (50 mL) and DMF (2 mL). The reaction was stirred at room temperature for 1 h and quenched with water. The insoluble material was filtered off and the solvent was removed. Purification by column chromatography (SiO2, CH2Cl2/heptane 1:4) yielded 3.44 g (63%) of the title compound: 1H NMR (CDCl3) δ 7.42–6.63 (m, 5 H), 1.66 (sept, J=8 Hz, 3 H), 1.10 (d, J=8 Hz, 18H; MS (ESI) 354.4 (M+H)+; Purity (HPLC) >95%.

Workup

  1. customquenched with water
  2. filtrationThe insoluble material was filtered off
  3. customthe solvent was removed
  4. customPurification by column chromatography (SiO2, CH2Cl2/heptane 1:4)

Sources & evidence

ORD record
ord-9383343bf1f34e75aa73808efae7bd08
Source dataset
uspto-grants-2006_08
Patent number
US07087750B2

Linked notes

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