Catalytic and Stoichiometric Synthesis of Indolylmaleimides
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good selectivity and yield (71%, Table 2, Entry 2). By in-
creasing the temperature, 1-methyl-4-(2-methyl-3-indolyl)-
3-(4-morpholinyl)maleimide (12) was maintained in high
yield (88%, Table 2, Entry 4). Similarly, 3-amino-4-indolyl-
maleimides 13 and 14 were isolated in 69% and 75% yield,
when NEt3 was applied as base (Table 2, Entries 5 and 6).
Finally, 3-bromo-1-methyl-4-(2-methyl-3-indolyl)maleimide
was treated with tryptamine and tyramine in the presence
of 2 equiv. NEt3 to give the corresponding 3-amino-4-indol-
ylmaleimides 15 and 16 in 70% and 89% yield, respectively
(Table 2, Entries 7 and 8). All isolated products are bright-
coloured crystalline compounds.
[3]
Conclusions
In summary, we have demonstrated that 3-bromo-1-
methyl-4-(2-methyl-3-indolyl)maleimide can successfully be
carbonylated with alcohols or amines in the presence of
Pd(OAc)2/di-1-adamantyl-n-butylphosphane (cataCXium®
A). The resulting 3-alkoxycarbonyl-4-indolylmaleimides
and 3-aminocarbonyl-4-indolylmaleimides were obtained in
25–70% yields. Stoichiometric amination of 3-bromo-1-
methyl-4-(2-methyl-3-indolyl)maleimide was carried out to
synthesize several novel 3-amino-4-indolylmaleimides in
good yields. Biological tests of the isolated compounds are
currently in progress.
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Acknowledgments
The authors thank S. Giertz and Dr. D. Michalik for excellent tech-
nical and analytical assistance. Generous financial support from
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und Forschung (BMBF), and the DFG (Leibniz-Price) is gratefully
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