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Article Dans Une Revue Organic Process Research and Development Année : 2020

Optimized Synthesis of 7-Azaindazole by a Diels–Alder Cascade and Associated Process Safety

Vincent Le Fouler
  • Fonction : Auteur
Vincent Bizet
Marian Lanz
  • Fonction : Auteur
Fabrice Gallou
  • Fonction : Auteur
Corinne Bailly
  • Fonction : Auteur
Pascale Hoehn
  • Fonction : Auteur
Michael Parmentier
Nicolas Blanchard

Résumé

Although pyrimidines are not among the most reactive partners in intramolecular inverse-electron demand [4ps+2ps] reactions with alkynes, they could be activated under mild and practical conditions, leading to fused nitrogen-containing heterocycles. We report an optimized synthesis of a 5-iodo-7-aza-indazole by a one-pot Diels-Alder cascade that starts from a pyrimidine substituted in the 2-position by an (alkynyl)hydrazone. The safety of the process and the environmental impact were thoroughly evaluated. Eventually, a selection of cross-coupling reactions of 17 was studied and allowed the introduction of carbon-and nitrogen-based nucleophiles at the C5-position in good to excellent yields.

Domaines

Chimie
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Dates et versions

hal-02991836 , version 1 (06-11-2020)

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Nicolas Brach, Vincent Le Fouler, Vincent Bizet, Marian Lanz, Fabrice Gallou, et al.. Optimized Synthesis of 7-Azaindazole by a Diels–Alder Cascade and Associated Process Safety. Organic Process Research and Development, 2020, 24 (5), pp.776-786. ⟨10.1021/acs.oprd.0c00184⟩. ⟨hal-02991836⟩
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