halogenating alkyltryptamines

[psycosmo]

If one were to treat an NN, dialkylated tryptamine with say Cl2, I2, or Br2, what position(s) on the aromatic ring would the halogen end up on? How does the fact that the pyrrole is attached to 2 positions on the benzene effect ortho-para substitution?
Anyway, is there any chance that the halogen might end up in the 4- position?
I note that in descriptions of the psilocin biosynth pathway the OH as added after N-alkylation
If this is so then It might be interesting to treat some plant xTracts with a halogen, then NaOH....

[Rhodium]

I don't know for sure, but I'm afraid that regular halogenation would place the halogen in the 2-position on the indole ring. But besides that, the 5-position is the most activated spot on the benzene part of the molecule.

[Stonium]

Is this a topic for the Newbee forum?

Oh/Well,
Stonium
_{Actually officer, if you factor in the earth's rotation, we were all speeding.}

[Lilienthal]

It's the 2-position which will be substituted.

[megamole]

If you halogenate using Br₂, you will get a mixture of 5- and 7- halogenation. The nitrogen in the 1-position activates the benzene ring, i.e. ortho-,para-directing, respective to itself. You can select the 5-position by acetylating the 1-position, which provides steric hindrance to protect the 7-position. Alternatively, you can halogenate exculsively the 7-position by selecting a halogenating agent that coordinates with the amine (the reagent escapes me at the moment.)
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