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Generated: February 17, 2018

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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
Application Number:08/469,961
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.
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