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Synlett 1996; 1996(9): 931-932
DOI: 10.1055/s-1996-5631
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Regioselective and Non-reductive C3-Debromination of Indole Nucleus1

Masanobu Tani, Makiko Goto, Mikiko Shimizu, Yoko Mochimaru, Junko Amemiya, Nobuko Mizuno, Rika Sato, Yasuoki Murakami*
  • *School of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274, Japan, Fax +81(474)72-1595
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Publication Date:
31 December 2000 (online)

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A method of debromination of 3-bromoindole derivatives was developed. Various ethyl 3-bromoindole-2-carboxylates were treated with H2SO4 and LiBr in acetic acid to give corresponding C3-debrominated indoles in excellent yields. The same reaction of 3-bromo-N-tosylindoles gave lower yields. The present reaction shows the possibility of indolic C3-protection by bromine atom.

indole - debromination - N-methylpyrrole - 1,3-dimethoxybenzene