Efficient access to 2-aryl-3-substituted benzo[b]thiophenes

Emilie David; Julie Perrin; Stéphane Pellet-Rostaing; Jérémie Fournier dit Chabert; Marc Lemaire

doi:10.1021/jo0500378

Efficient access to 2-aryl-3-substituted benzo[b]thiophenes

J Org Chem. 2005 Apr 29;70(9):3569-73. doi: 10.1021/jo0500378.

Authors

Emilie David¹, Julie Perrin, Stéphane Pellet-Rostaing, Jérémie Fournier dit Chabert, Marc Lemaire

Affiliation

¹ Université Claude Bernard Lyon 1, Laboratoire de Catalyse et Synthèse Organique, CPE bât 308, UMR 5181, 43 Bd du 11 novembre 1918, 69622 Villeurbanne Cedex, France.

PMID: 15844992
DOI: 10.1021/jo0500378

Abstract

[reaction: see text] Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-arylbenzo[b]thiophenes with heteroatoms at the 3-positions directly from the benzo[b]thiophene core by using an aromatic nucleophilic substitution reaction and Heck-type coupling. This methodology provides 2-aryl-3-amino or phenoxybenzo[b]thiophenes in about 35% overall yield in 5 steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Molecular Structure
Oxidation-Reduction
Piperidines / chemistry
Raloxifene Hydrochloride / chemistry
Selective Estrogen Receptor Modulators / chemical synthesis*
Selective Estrogen Receptor Modulators / pharmacology
Structure-Activity Relationship
Thiophenes / chemical synthesis*
Thiophenes / chemistry
Thiophenes / pharmacology

Substances

Piperidines
Selective Estrogen Receptor Modulators
Thiophenes
benzothiophene
Raloxifene Hydrochloride
LY 353381