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Claims for Patent: 5,808,061

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Claims for Patent: 5,808,061

Title: Intermediates and processes for preparing benzothiophene compounds
Abstract:The present invention provides a novel process for preparing a compound of formula I ##STR1## wherein R.sup.1 and R.sup.2 combine to form C.sub.4 -C.sub.6 polymethylene, --CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 --, --CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; or a pharmaceutically acceptable salt or solvate thereof. Also provided intermediates of formulae II and IV ##STR2## wherein Z is a leaving group.
Inventor(s): Dodge; Jeffrey A. (Indianapolis, IN), Stocksdale; Mark G. (Fishers, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Application Number:08/503,444
Patent Claims: 1. A process for preparing a compound of formula I ##STR22## wherein R.sup.1 and R.sup.2 combine to form C.sub.4 -C.sub.6 polymethylene, --CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 --, --CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; or a pharmaceutically acceptable salt or solvate thereof, comprising

a) reacting a compound of formula II ##STR23## with a compound of formula Z--CH.sub.2 --CH.sub.2 --Z in which Z is the same or different leaving group, and reacting the resulting compound of formula IV ##STR24## wherein Z is a leaving group, with pyrrolidine, piperidine, hexamethyleneimine, methylpyrrolidine, dimethylpyrrolidine, or morpholine;

b) deprotecting the 6- and 4'-position hydroxy group of the reaction product of step a); and

c) optionally salifying or forming a solvate of the reaction product of step b).

2. The process of claim 1 wherein R.sup.1 and R.sup.2 combine to form C.sub.4 -C.sub.6 polymethylene.

3. The process of claim 2 wherein R.sup.1 and R.sup.2 combine to form C.sub.5 polymethylene.

4. The process of claim 3 wherein said salt thereof is the hydrochloride salt.

5. The process of claim 4 wherein each Z is bromo.

6. The process of claim 1 wherein each Z is bromo.

7. The process of claim 5 which is carried out in a single vessel.

8. The process of claim 1 which is carried out in a single vessel.

9. A process for preparing a compound of formula I ##STR25## wherein R.sup.1 and R.sup.2 combine to form C.sub.4 -C.sub.6 polymethylene, --CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 --, --CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; or a pharmaceutically acceptable salt or solvate thereof, comprising

a) reacting a compound of formula II ##STR26## with a compound of formula III ##STR27## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of triphenylphosphine and diethyl azodicarboxylate;

b) deprotecting the 6- and 4'-position hydroxy group of the reaction product of step a); and

c) optionally salifying or forming a solvate of the reaction product of step b), wherein the process is carried out in a single vessel.

10. The process of claim 9 wherein R.sup.1 and R.sup.2 combine to form C.sub.4 -C.sub.6 polymethylene.

11. The process of claim 10 wherein R.sup.1 and R.sup.2 combine to form C.sub.5 polymethylene.

12. The process of claim 11 wherein said salt thereof is the hydrochloride salt.

13. A compound of formula IV ##STR28## wherein Z is a leaving group.

14. A compound of claim 13 wherein said leaving group is bromo, chloro, or iodo.

15. A compound of claim 14 wherein said leaving group is bromo.
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