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N-methyl lithiation of N-methylindoles directed by α-amino alkoxides

✍ Scribed by Daniel L. Comins; Michael O. Killpack

Book ID
104229506
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
200 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel N-methyl lithiafion-alkylation of an a-amino alkoxide derived from 3-chloro-Nmethylindole-Z-carboxaldehyde is described.

The reaction of aromatic aldehydes with certain lithium dialkylamides gives a-amino alkoxides in situ that can be ring lithiated with alkyllithiums. Alkylation and hydrolysis on workup provides orthosubstituted aryl aldehydes via a one-pot reaction.2J This methodology works well for the one-pot substitution of heterocyclic aromatic aldehydess as well as for benzaldehyde derivative& We previously reported that attempted C-3 lithiation of the a-amino alkoxide derived from N-methyl-2pyrrolecarboxaldehyde and lithiated N,N,N'-trimethylethylenediamine gave metalation solely on the N-methyl group. When we tried to extend this novel directed lithiation to N-methylindole-2carboxaldehyde, lithiation-methylation of the a-amino alkoxide prepared from N,N,N'trimethylethylenediamine gave a mixture of 1 -ethylindole-2-carboxaldehyde and 1,3-dimethylindole-2-

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