Efficient access to 2-aryl-3-substituted benzo[b]thiophenes.
[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.
David
Emilie
E
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.
Perrin
Julie
J
Pellet-Rostaing
Stéphane
S
Fournier dit Chabert
Jérémie
J
Lemaire
Marc
M
D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry; D020849:Raloxifene Hydrochloride / Q000737:chemistry; D020845:Selective Estrogen Receptor Modulators / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D010880:Piperidines; D020845:Selective Estrogen Receptor Modulators; D013876:Thiophenes; C088015:benzothiophene; D020849:Raloxifene Hydrochloride; C115121:LY 353381