Alkylation novel 3-substituted indoles

Any other synthesis that leads to a 2,3-dialkylindole can of course be considered, and several novel reported routes are mentioned later. Vigorous alkylation of a 2-substituted indole can introduce three identical alkyl groups for example, the best route to 1,3,3-triethylFischer s base is exhaustive ethylation of 2-methylin-dole,15 and methylation of 2-phenylindole also introduces three alkyl groups. 

Deprotonation of indoles 128 followed by alkylation with 2-methyloxirane led to the secondary alcohols 129 that were used as starting compounds in the preparation of substituted 2-(l//-indol-l-yl)-l-methylethylamines 130, novel agonists of 5HT2C receptors. Sn2 reaction of the corresponding mesylates with sodium azide and reduction of the azides with either hydrogen or LiAlH4 produced amines 130 in excellent yields (Scheme 28) <1997JME2762>. 

A radical tpso-type substitution on indoles and benzofurans has resulted in other dearomatized spirocycles [83]. Aryl, vinyl, and alkyl radicals added to the C-2 position of the indole to give novel compounds, 128,130, and 132, in moderate to excellent yields. In the case of the addition of alkyl radicals, significant amounts of the reduced starting material were also isolated. 

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