The bromination–methanolysis of N-acetyl-2,3-dimethylindole

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Abstract
Bromination of N-acetyl-2,3-dimethylindole 11 in the presence of excess methanol at room temperature gave a mixture of products consisting of cis and transN-acetyl-2,3-dimethoxy-2,3-dimethylindoline 17 and 18,3-methoxy-2,3-dimethylindolenine 19, and N-acetyl-3-methoxymethyl-2-methylindole 21. The same reaction performed at −40 °C yielded a mixture of 17, 18, and N-acetyl-2-methoxy-2-methyl-3-methyleneindoline 22. Bromination of 11 at low temperature in the presence of 1.5 equivalents of methanol followed by treatment with triethylamine yielded 22 quantitatively. Treatment of 22 with acidic methanol readily gave 21. The mechanistic implications of these transformations are considered.

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