Claims for Patent: 5,808,061

Summary 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 R1 and R2 combine to form C4 -C6 polymethylene, --CH2 CH(CH3)CH2 CH2 --, --CH2 C(CH3)2 CH2 CH2 --, or --CH2 CH2 OCH2 CH2 --; 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):	Jeffrey A. Dodge, Mark G. Stocksdale
Assignee:	Eli Lilly and Co
Application Number:	US08/503,444
Patent Claims:	1. A process for preparing a compound of formula I ##STR22## wherein R1 and R2 combine to form C4 -C6 polymethylene, --CH2 CH(CH3)CH2 CH2 --, --CH2 C(CH3)2 CH2 CH2 --, or --CH2 CH2 OCH2 CH2 --; or a pharmaceutically acceptable salt or solvate thereof, comprisinga) reacting a compound of formula II ##STR23## with a compound of formula Z--CH2 --CH2 --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 R1 and R2 combine to form C4 -C6 polymethylene. 3. The process of claim 2 wherein R1 and R2 combine to form C5 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 R1 and R2 combine to form C4 -C6 polymethylene, --CH2 CH(CH3)CH2 CH2 --, --CH2 C(CH3)2 CH2 CH2 --, or --CH2 CH2 OCH2 CH2 --; or a pharmaceutically acceptable salt or solvate thereof, comprisinga) reacting a compound of formula II ##STR26## with a compound of formula III ##STR27## wherein R1 and R2 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 R1 and R2 combine to form C4 -C6 polymethylene. 11. The process of claim 10 wherein R1 and R2 combine to form C5 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.