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Topic: Protecting the Nitrogen of pyridine  (Read 6916 times)

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Offline mahbod

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Protecting the Nitrogen of pyridine
« on: October 09, 2010, 11:21:21 AM »
Hi
Anybody knows any good way to protect and deprotect the nitrogen of the pyridine.
I have a pridine in my molecule and its bassicity interferes with my next step of the reaction.
 ???
Thank you in advance

Offline discodermolide

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Re: Protecting the Nitrogen of pyridine
« Reply #1 on: October 09, 2010, 12:43:43 PM »
Hi
Anybody knows any good way to protect and deprotect the nitrogen of the pyridine.
I have a pridine in my molecule and its bassicity interferes with my next step of the reaction.
 ???
Thank you in advance

a) it may help if you tell us about the next step.
b) you can protect by protonation or by making the N-oxide
Development Chemists do it on Scale, Research Chemists just do it!
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Offline mahbod

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Re: Protecting the Nitrogen of pyridine
« Reply #2 on: October 09, 2010, 11:44:59 PM »
I'm trying to react Ru(dppe)2Cl2 with my acetylene ligand that has a py group in it and i just want a mono acethylide product but having a bas group, I always end up with some bis acethylide that it is impossible to remove.

fentonh

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Re: Protecting the Nitrogen of pyridine
« Reply #3 on: October 10, 2010, 12:19:31 AM »
Hi
Anybody knows any good way to protect and deprotect the nitrogen of the pyridine.
I have a pridine in my molecule and its bassicity interferes with my next step of the reaction.
 ???
Thank you in advance
Methylation (e.g., using MeI or dimethylsulfate). Deprotect by treatment with Ph3P. This  is not a new trick. Also look in the Wuts & Greene book.

« Last Edit: October 10, 2010, 03:35:44 AM by Borek »

Offline mahbod

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Re: Protecting the Nitrogen of pyridine
« Reply #4 on: October 10, 2010, 07:04:39 AM »
thank you guys it was a big help

Offline sjb

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Re: Protecting the Nitrogen of pyridine
« Reply #5 on: October 10, 2010, 07:11:03 AM »
Seems to me the problem is more the reactivity of the alkyne, than the pyridine. Can you use a large excess of the ruthenium complex compared to the acetylenic pyridine?

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