I thought I had my own way of carrying out the synthesis but then i realized the stabilized chloro dimethyl ammonium salt i wanted to add was insoluble in nonpolar solvents.

I thought i could use an IAA stabilised trianion (formed by reaction of IAA with BuLi) as nucleophile [Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A Jan Bergman, Eva Koch and Benjamin Pelcman] add on the dimethyl amine followed by aqueous work up (think that would only work with an acid chloride derivative though)

I also gave michael addition a look but the alkyl chain is one kink too long :-)

Anyway heres a great paper using TCT as catalyst for solvent free michael reactions of indoles and pyroles. Enjoy!
SOme of you may recall the paper on TCT as efficient catalyst for turning alcohols in alkyl chlorides...I think I found that here.

An other way to indole 3 acetic acid:

Normal indole is an available chemical. At us, it is sold relative cheap (100g/25 euro). From this compound there are a lot of ways to get indole 3 acetic aciid what is the direct precursor of the DMT. Let's see an easy way:

Normal indole with diazoacetic acid ethyl ester in boiling ether gives indole 3 acetic acid ethyl ester. The diazoacetic acid loses the diazo part of the molecule and it just get's on the indole. The formation of the IAA ethyl ester is almost near to 90%. The reaction was described by Jackson in 1935.

The precusors are not hard to get. As I wrote, the indole is available in chem. supply shops. The diazo acetic acid ethyl ester can be made from glycine.

Synthesis of diazo acetic acid ethyl ester:
  from   

The glycine ethyl ester HCl is made by adding glycine to EtOH and bubbling dry HCl gas through it at 65-70 Celsius. The EtOH is also the solvent, so use more that the calculated amount. EtOH slould be added again and again to the reaction, because it will boil out from the mixture. You can get a recipe here: http://www.jbc.org/content/175/2/531.full.pdf
The ethyl ester should be diazotated with NaNO2. This part of the reaction is not so hard. Just cool down the chemicals, get a solvent what dissolves both ot the components (the NaNO2 and the glycine ethyl ester HCl). The glycine ethy ester HCl is soluble in ethanol, methanol, ether, benzne. Maybe the best would be to use methanol as a solvent (sodium-nitrite solubility in methanol: 4.4 g / 100 g 20°C). The diazo acetic acid ethyl ester is a yellow oily liquid. -22 Celsius melting point, boiling point, 140-141 Celsius.

The glycine ethyl ester is soluble in ether so just dissolve it in ether, add the indole to it and start to boil it. After the calculated amount of N2 evolved you are ready with the indole 3 acetic acid ethyl ester. Now you should just add the dimethyl amine to the mixture. And hydrogenate it to get the pure DMT.

-Evilblaze

I am missing something. IAA is pretty OTC and not that costly so it should be of least concerns as reagent.
Synth. the IAA-methyl ester would be easy too as described in rhodium/chemistry/indoleaceticacid.html

Just at which point does glycine ethyl ester HCl take part in the reaction? And how can this skip the LiAlH4 step which due to
the chemical involved would be hard to pull off?

It just seemed too straight to me, IAA, glycine, NaNO2, dimethylamine.

Thank you

Good sources for bulk IAA for use as growth hormone are out there (or at least used to be a couple of years ago).

I was always thinking along the lines of IAA -> ester -> dimethylamide, followed by electroreduction. There are refs describing just that for N,N-dimethylphenethylamine as the final product. So it should work on indoles, only indoline formation being of possible worry, but I don't think that will happen under electroreduction conditions (which are similar to nitroalkene electroreduction, acidic environment). You'll need NaBH4 or catalytic hydrogenation for that to happen.

Catalytic hydrogenation is not a good idea when reducing indolic substrates, you will have indoline formation.

I mentioned electroreduction not catalytic hydrogenation (nor electrocatalytic hydrogenation).

I would like to share the ref, but can't find it back for the moment in my ungodly pile of papers. Do some searching on the electroreduction of amides, it's out there.