Tetrahedron p. 5955 - 5970 (1989)
Update date:2022-08-02
Topics:
Masters, N. F.
Mathews, N.
Nechvatal, G.
Widdowson, D. A.
7-Substituted indoles were prepared by the lithiation - electrophilic quenching of 1-methyl-, 1-methoxymethyl-, and 1-(2-trimethylsilylethoxymethyl)indoletricarbonylchromium(0) complexes.C-2 of the 1-methylindole series had to be blocked to achieve subsequent 7- (and 4-) metallation, but the other series could be directly metallated at C-7 without attack at C-4 by 1-alkoxymethyl directed lithiation.Metallation at C-2 in the 1-alkoxymethyl series was avoided by the use of 2-trimethylsilyl or the 3-methyl analogues.No conditions were found to effect the removal of the methoxymethyl group, but the 2-trimethylsilylethoxymethyl group was efficiently cleaved with 'anhydrous' tetrabutylammonium fluoride.
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