[Dan]

Alkylations and acylations more often occur at the C-3 position.

There is a large volume of literature demonstrating that indoles can be N-benzoylated in very high yields using triethylamine/DMAP, as well as procedures using NaH, hydoxide/PTC. There is a similar body of examples for N-benzylation (usually using NaH, hydroxide or carbonate bases). I really don't think the reaction in question is going to be as difficult as you suggest.

An example: N-Benzoylation of 5-methylindole with BzCl/NEt₃/DMAP in 96% yield (see scheme 1, reaction 8 9)

An example: N-Benzylation of indole with BnCl/KOH in 92% yield (compound 3e on pS9)

[TwistedConf]

I really don't think the reaction in question is going to be as difficult as you suggest.

Right---  In general, it's not.  The original poster is most likely having trouble with his reagents/technique or running into something unexpected with all the other functionality there.

In the original message you mentioned working from a paper.  Can you post the reference?

[schen]

@Dan ..Thanks for the reference and yes it is Benzoyl chloride not Benzyl Chloride.

@Doc Oc.. I am working on the Structure Activity Relationship study of the molecule and by acylation, my hypothesis is that it will have better biological activity than the lead compound. So, I can not continue further without acylation.

@ Camptzak... I assume that one pair of electrons will be involved with in the molecule and the other pair will be readily available for reaction, making it Nucleophilic. But I am having trouble with deprotonation, were I am struck at.