Butyl iodide → 3-butyl-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole

HRID 1767965Notes

Reaction equation

HRID 1767965 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:9]=2)[N:4]([Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:3]=1.I[CH2:27][CH2:28][CH2:29][CH3:30].C([Li])(C)(C)C>>[CH2:27]([C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:9]=2)[N:4]([Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:3]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 10962Butyl iodideHCID 236144893-bromo-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indoleHCID 178418306HCID 178418306, compound

Product 1

HCID 236144913-butyl-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole

Procedure

In analogy to the procedure described in example 27 c], 3-bromo-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole was reacted with 1-iodobutane in the presence of tert-butyllithium to form 3-butyl-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole as dark brown oil.

Sources & evidence

ORD record
ord-2ddc3fd1580c4d7b8c7b2b46688d53b6
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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