Processes for the preparation of sumatriptan and related...

C - Chemistry – Metallurgy – 07 – C

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C07C 303/40 (2006.01) C07C 311/35 (2006.01) C07D 209/14 (2006.01)

Patent

CA 2389514

The present invention relates to a process for preparing phenylhydrazines of formula (I) in which R represents CH2SO2NHCH3, CH2CH2SO2Ph, CH2CH2SO2NHMe or a group of structure (A), (B), (C), in which a diazonium salt of formula (II) in which X represents an anion derived from hydrochloric acid, sulphuric acid, acetic acid, phosphoric acid, tetrafluoroboric acid or hydrobromic acid is reduced by a dithionite salt. The resulting phenylhydrazines can be converted to the corresponding indole derivatives by the Fischer indole synthesis.

La présente invention se rapporte à un procédé de préparation de phénylhydrazines de formule (I) dans laquelle R représente CH¿2?SO¿2?NHCH¿3?, CH¿2?CH¿2?SO¿2?Ph, CH¿2?CH¿2?SO¿2?NHMe ou un groupe de structure (A), (B), (C), consistant à réduire par un sel de dithionite un sel de diazonium représenté par la formule (II), dans laquelle X représente un anion dérivé de l'acide chlorhydrique, de l'acide sulfurique, de l'acide acétique, de l'acide phosphorique, de l'acide tétrafluoroborique ou de l'acide bromhydrique. Les phénylhydrazines résultantes peuvent être transformées en dérivés indole correspondants par une synthèse d'indole de Fischer.

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