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A facile approach to the synthesis of 5,7-disubstituted indoles via a highly selective lithium–bromine exchange of 5,7-dibromoindoles

✍ Scribed by Lianhai Li; Andrew Martins

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
140 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A general approach to the synthesis of 5,7-disubstituted indoles has been developed based upon a highly selective lithium-bromine exchange reaction at the 7-position when 1-alkyl-5,7-dibromoindoles were treated with t-BuLi in ether. The resulting 5-bromo-7-lithiated indoles could react with various electrophiles to afford 5-bromo-7-substituted indoles (6) upon work-up. Without isolation of 6, the intermediates thus obtained could be exposed to a second lithium-bromine exchange reaction in a one-pot procedure and further reacted with various electrophiles to afford 5,7-disubstituted indoles (1).

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