Non??Steroidal antiinflammatory agents. 1. A novel synthesis of 1??methyl??5??p??tolylpyrrole??2??acetic acid (tolmetin)

…, F Corelli, S Massa, G Stefancich

Index: Artico; Corelli; Massa; Stefancich Journal of Heterocyclic Chemistry, 1982 , vol. 19, # 6 p. 1493 - 1495

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Citation Number: 13

Abstract

Abstract A four-step preparation of 1-methyl-5-p-totylpyrrole-2-acetic acid (Tolmetin) is reported starting from 1-methyl-2-p-tolylpyrrole. Formylation of this compound followed by condensation with methyl (methylthio)-methyl sulfoxide furnished 1-(methylsulfinyl)-1- methylthio-2-(1-methyl-5-p-tolyl-2-pyrrolyl) ethylene. Pummerer rearrangement of the latter compound gave ethyl 1-methyl-5-p-tolylpyrrole-2-acetate, which was hydrolyzed in ...