Process for the preparation of 3-alkanoyl- and 3-alkylindoles

C - Chemistry – Metallurgy – 07 – D

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C07D 209/10 (2006.01) C07D 209/12 (2006.01)

Patent

CA 2355138

Process for the preparation of compounds of the formula I (see formula I) in which R, R1, R2 and n are as defined in Claim 1, and X is O or H,H and their acid addition salts, characterized in that a) if X is O and R, R1, R2 and n are as defined above, a compound of the formula II (see formula II) in which R1 and R2 are as defined in Claim 1 is reacted with a compound of the formula III R-(CH2)n-CO-L III in which R, L and n are as defined in Claim 1 in a Friedel-Crafts acylation with catalysis of Lewis acid metal halides of the type R'-Al(Cl)2, in which R' is as defined in Claim 1, or b) if X is H,H and R, R1, R2 and n are as defined above, a compound of the formula I in which X is O and R, R1, R2 and n are as defined above, is reduced using complex hydrides with activation by Lewis acid metal halides of the type R'-Al(Cl)2, in which R' is as defined in Claim 1, and/or in that a resulting base of the formula I is converted into one of its acid addition salts by treatment with an acid.

L'invention concerne un procédé pour la production de composés de formule (I), dans laquelle R, R<1>, R<2> et n ont la signification donnée dans la revendication 1, et X représente O ou H,H, et pour la production de leurs sels d'addition d'acide. Ce procédé est caractérisé en ce que a) lorsque X représente O et R, R<1>, R<2> et n ont la signification indiquée, on fait réagir un composé de formule (II), dans laquelle R<1> et R<2> ont la signification donnée dans la revendication 1, avec un composé de formule (III): R-(CH2)n-CO-L, dans laquelle R, L et n ont la signification donnée dans la revendication 1, au cours d'une acylation de Friedel-Crafts avec catalyse d'halogénures métalliques contenant des acides de Lewis, du type R'-Al(Cl)2, R' ayant la signification donnée dans la revendication 1, ou b) lorsque X représente H,H et R, R<1>, R<2> et ont la signification indiquée, on réduit un composé de formule (I), dans laquelle X représente O et R, R<1>, R<2> et n ont la signification indiquée, avec des hybrides complexes, avec activation par des halogénures métalliques contenant des acides de Lewis, du type R'-Al(Cl)2, R' ayant la signification donnée dans la revendication 1, et/ou on convertit une base obtenue, de formule (I), par traitement avec un acide, en un de ses sels d'addition d'acide.

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