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A Novel Process For Preparation Of Intermediates Of Eletriptan

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.

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Patent Information

Application #
Filing Date
25 August 2009
Publication Number
08/2012
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application

Applicants

SMS PHARMACEUTICALS LIMITED
# 417 NILGIRI ADITYA ENCLAVE AMEERPET HYDERABAD 500 038

Inventors

1. Sanjay Kumar Dehury
SMS Pharma Research Center Survey No 186 189 & 190; Gagillapur (Vil); Quthbullapur (Mo); Rangareddy (Dt) Andhra Pradesh; India
2. Hariharakrishnan Venkata Subhramanian
SMS Pharma Research Center Survey No 186 189 & 190; Gagillapur (Vil); Quthbullapur (Mo); Rangareddy (Dt) Andhra Pradesh; India
3. Venkata Srihari Tadimalla
SMS Pharma Research Center Survey No 186 189 & 190; Gagillapur (Vil); Quthbullapur (Mo); Rangareddy (Dt) Andhra Pradesh; India
4. Hari Prasad Kodali
SMS Pharma Research Center Survey No 186 189 & 190; Gagillapur (Vil); Quthbullapur (Mo); Rangareddy (Dt) Andhra Pradesh; India
5. Ramesh Babu Potluri
SMS Pharma Research Center Survey No 186 189 & 190; Gagillapur (Vil); Quthbullapur (Mo); Rangareddy (Dt) Andhra Pradesh; India

Specification

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.

Documents

Application Documents

# 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