tert-Butyldimethylsilyl chloride → 3-bromo-1-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-1H-indole

HRID 1767983Notes

Reaction equation

HRID 1767983 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[Br:26]N1C(=O)CCC1=O>>[Br:26][C:11]1[C:10]2[C:14](=[CH:15][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])=[CH:8][CH:9]=2)[N:13]([Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:12]=1

Participants

4

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67184N-bromobutanimideHCID 222508166-((tert-butyldimethylsilyl)oxy)-1H-indole

Product 1

HCID 236144903-bromo-1-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-1H-indole

Procedure

In analogy to the procedure described in example 27 b], 6-(tert-butyl-dimethyl-silanyloxy)-1H-indole was reacted with tert-butyldimethylsilyl chloride and subsequently with N-bromosuccinimide to obtain 3-bromo-1-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-1H-indole as brown solid.

Sources & evidence

ORD record
ord-720d8c1f05074d618f4b217a3bb19e6c
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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