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Paper | Regular issue | Vol 51, No. 7, 1999, pp.1585-1591
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8543
Synthesis and Reaction of Dimethyl 7-Bromoindole-2,3-dicarboxylates

Yasuyoshi Miki,* Ko-ichi Matsushita, Hajime Hibino, and Hideaki Shirokoshi

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan


Reaction of 1-(4-benzyloxyphenyl)-2-phenylhydrazine with dimethyl acetylenedicarboxylate (DMAD) gave dimethyl 5-benzyloxyindole-2,3-dicarboxylate and dimethyl indole-2,3-dicarboxylate. However, treatment of 1-(2-bromo-phenyl)-2-phenylhydrazine with DMAD afforded dimethyl 7-bromoindole-2,3-dicarboxylate, exclusively. In a similar manner, dimethyl 7-bromo-5-methoxy-indole-2,3-dicarboxylate was also obtained from 1-(2-bromo-4-methoxyphenyl)-2-phenylhydrazine. The bromo group of dimethyl 7-bromoindole-2,3-dicarboxylate was converted to an 1-ethoxyvinyl or vinyl group by treatment with tributyl-(1-ethoxyvinyl)tin or tributyl(vinyl)tin in the presence of a Pd(0) catalyst.