|Title:|| Synthesis of 3-[4-(2-aminoethoxy)-benzoyl]-2-aryl-6-hydroxybenzo[b]thiophenes|
|Abstract:||The present invention is directed to chemical processes for preparing 2-aryl-6-hydroxy-3-[4-(2-aminoethoxy)benzoyl]benzo[b]-thiophenes. The present invention is also directed to crystalline solvates and a non-solvated crystalline form of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]-benzo[b]th iophene hydrochloride, as well as processes for their preparation.|
|Inventor(s):|| LaBell; Elizabeth Smith (Lafayette, IN), McGill; John McNeill (Lafayette, IN), Miller; Randal Scot (Lafayette, IN) |
|Assignee:|| Eli Lilly and Company (Indianapolis, IN) |
|Filing Date:||Jun 06, 1995|
|Claims:||1. A process for preparing a compound of the formula: ##STR14## |
comprising acylating a benzothiophene of the formula: ##STR15##
wherein: R.sup.4 is C.sub.1 -C.sub.4 alkoxy; and R.sup.5 is C.sub.1 -C.sub.4 alkyl;
with an acylating agent of the formula: ##STR16##
wherein: R.sup.6 is chloro, bromo, or hydroxyl;
in the presence of a solvent and boron trichloride.
2. The process of claim 1 wherein R.sup.6 is chloro.
3. The process of claim 1 wherein R.sup.4 is methoxy, and R.sup.5 is methyl.
4. The process of claim 3 wherein the reaction solvent is one or more solvents selected from the group consisting of chloroform, methylene chloride, chlorobenzene, 1,2-dichloroethane, 1,2,3-trichloropropane, 1,1,2,2-tetrachloroethane, 1,2-dichlorobenzene, bromobenzene, and fluorobenzene.
5. The process of claim 3 wherein the solvent is methylene chloride.