Dimethylformamide → 5-iodo-1-triisopropylsilanyl-1H-indole

HRID 1890374Notes

Reaction equation

HRID 1890374 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CN(C=O)C.[H-].[Na+].[CH:18]([Si:21]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])Cl)([CH3:20])[CH3:19]>C(Cl)Cl.O>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:21]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:18]([CH3:20])[CH3:19])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 27823135-Iodo-1H-indole

Product 1

HCID 685972215-iodo-1-triisopropylsilanyl-1H-indole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-Iodo-1H-indole (5.0 g, 20.57 mmol) was dissolved in CH2Cl2 (50 ml) and DMF (1 ml) and cooled to 0° C. Sodium hydride (1.234 g, 30.86 mmol) was added in small portions, and the reaction mixture was stirred for 30 minutes at 0° C. Triisopropylchlorosilane (4.54 ml, 20.57 mmol) was added slowly to the reaction mixture, and stirring was continued for 1 hour. Cold water (200 ml) was added to the reaction mixture, which was extracted twice with ethyl acetate (100 ml).

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. extractionwas extracted twice with ethyl acetate (100 ml)

Sources & evidence

ORD record
ord-06590d992bf946ffb38ddb158a5cb7cc
Source dataset
uspto-grants-2013_08
Patent number
US08507469B2

Reaction notes

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