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Generated: January 19, 2018

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Title: Process for preparing 3-(4-aminoethoxybenzoyl)benzo[b]thiophenes
Abstract:The use of particularly advantageous protecting groups for the hydroxy groups of 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophenes provides a high-yielding process for the preparation of such compounds having a 4-(2-aminoethoxy)benzoyl 3-group.
Inventor(s): Jones; Charles D. (Indianapolis, IN), Goettel; Mary E. (Chesterland, OH)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Filing Date:Apr 03, 1981
Application Number:06/246,334
Claims:1. A process for preparing a compound of the formula ##STR8## wherein R.sup.1 and R.sup.2 are independently C.sub.1 -C.sub.4 alkyl, or combine to form C.sub.4 -C.sub.6 polymethylene or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; which process comprises acylating a compound of the formula ##STR9## wherein R is --COR.sup.3 or --SO.sub.2 CH.sub.3, and R.sup.3 is methyl, phenyl, p-tolyl, p-anisyl, or mono- or di(halo or nitro)phenyl; under Friedel-Crafts conditions with an acylating agent of the formula ##STR10## wherein R.sup.5 is X or ##STR11## X is chloro, bromo or --SO.sub.2 R.sup.3 ; and R.sup.4 is chloro, bromo, iodo, or an activating ester group; when R.sup.5 is X, displacing the X group with an amine of the formula ##STR12## and cleaving the R groups.

2. A process of claim 1 wherein the starting compound is a compound wherein R is --COR.sup.3.

3. A process of claim 2 wherein the starting compound is a compound wherein R.sup.3 is methyl.

4. A process of claim 2 wherein the starting compound is a compound wherein R.sup.3 is phenyl.

5. A process of claim 2 wherein the starting compound is a compound wherein R.sup.3 is p-anisyl.

6. A process of claim 1 wherein the starting compound is a compound wherein R is --SO.sub.2 CH.sub.3.

7. A process of any one of claims 1-6 wherein the acylating agent is a compound wherein R.sup.5 is pyrrolidino or piperidino.

8. A process of claim 7 wherein the acylation is in the presence of aluminum chloride.

9. A process of claim 7 wherein the acylation is in the presence of trifluoromethanesulfonic acid.

10. A process of claim 8 wherein the acylating agent is a compound wherein R.sup.4 is chloro or bromo.

11. A process of claim 9 wherein the acylating agent is a compound wherein R.sup.4 is chloro or bromo.

12. A process of any one of claims 1-6 wherein the acylating agent is a compound wherein R.sup.5 is X.

13. A process of claim 12 wherein the acylating agent is a compound wherein X is chloro or bromo.

14. A process of claim 13 wherein the acylation is in the presence of aluminum chloride.

15. A process of claim 14 wherein the acylating agent is a compound wherein R.sup.4 is chloro or bromo.

16. A process of claim 13 wherein the acylation is in the presence of trifluoromethanesulfonic acid.

17. A process of claim 16 wherein the acylating agent is a compound wherein R.sup.4 is chloro or bromo.

18. A process of claim 12 wherein the group X is displaced with piperidine or pyrrolidine.

19. A process of claim 13 wherein the group X is displaced with pyrrolidine or piperidine.
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