Abstract: The present invention reveals a novel process for the one of the key intermediates of eletriptan. The process involves heck coupling of the indole derivative with phenyl vinyl sulphone to render the corresponding product.
DESCRIPTION:
The present process involves the conversion of iodoindole to the N-sustituted derivatives with protecting groups such as acetyl, benzoyl or benzyl. Further the N-protected derivative was reacted with (R)-benzyl 2-(chlorocarbonyl)pyrrolidine-l-carboxylate in presence of ethylmagensium bromide to render the N-substituted benzyl (2R)-2-[(5-iodo- lH-indol-3-yl)carbonyl]pyrrolidine-l-carboxylate derivative. It was subjected to reduction with Vitride to afford 5-iodo-3-(((R)-l-methylpyrrolidin-2-yl)methyl)-1H- indole derivative followed by heck coupling with phenyl vinyl sulphone in presence of palladium catalyst to render a product of formula III.
CLAIMS;
We claim
1. heck coupling of indole derivative of formula I
with with phenyl vinyl sulphone formula II
to render the corresponding product of formula III
Where R1 is H or [(2R)-l-Methyl-2-pyrrolidinyl]methyl and R2 is benzyl, acetyl or benzoyl.
2. The process of claim 1, wherein the heck coupling is catalyzed by palladium catalyst.
3. The process of claim 1, wherein the heck coupling is carried out in the absence of any phosphene based ligand.
4. The process of claim 2, wherein the palladium catalyst is recycled.
| # | Name | Date |
|---|---|---|
| 1 | 2034-CHE-2009 CORRESPONDENCE OTHERS 12-02-2015.pdf | 2015-02-12 |
| 1 | 2034-che-2009 correspondence others 25-08-2010.pdf | 2010-08-25 |
| 2 | 2034-che-2009 abstract 25-08-2010.pdf | 2010-08-25 |
| 2 | Form-1.pdf | 2011-09-04 |
| 3 | 2034-che-2009 claims 25-08-2010.pdf | 2010-08-25 |
| 3 | 2034-che-2009 form-2 25-08-2010.pdf | 2010-08-25 |
| 4 | 2034-che-2009 description (complete) 25-08-2010.pdf | 2010-08-25 |
| 5 | 2034-che-2009 claims 25-08-2010.pdf | 2010-08-25 |
| 5 | 2034-che-2009 form-2 25-08-2010.pdf | 2010-08-25 |
| 6 | 2034-che-2009 abstract 25-08-2010.pdf | 2010-08-25 |
| 6 | Form-1.pdf | 2011-09-04 |
| 7 | 2034-CHE-2009 CORRESPONDENCE OTHERS 12-02-2015.pdf | 2015-02-12 |
| 7 | 2034-che-2009 correspondence others 25-08-2010.pdf | 2010-08-25 |