DMT from Me2N-CH2-COBr?

[Rhodium]

Would acylation of indole with Me2N-CH2-COBr work? Or would the tertiary amine interfer with the acyl halide in some way?

After that, the reduction of the carbonyl group would be very easy, yielding DMT.

[Greensnake]

Hmmm...... I would expect kinda serious mess on this route (I don't want  to say it's outright impossible, but quite a problems are to be expected) First, I doubt that it is possible to make free bromanhydride of N,N-dimehylglycine (without a salt on amine part). Second, indole acylation in 3 position is not exactly simplest thing on earth (indole can as well and preferably acylate on N; that standart dmt route via oxalylchloride is exception rather than rule, which is possible because oxalylchloride is not a typical chloranhydride)
Well, I can be wrong, I confess, that I'm a bit rusty in finesses of indole chemistry. Maybe some clever guys already discovered reliable ways of indole acylation (perhaps with nontraditional Lewis acid catalysis) and I just don't know them?

My personal half educated opinions only.  

Greensnake

[Rhodium]

Indole can be acylated with alpha-bromo-propionylbromide, as seen in

https://www.thevespiary.org/rhodium/Rhodium/chemistry/it-290.html

[Greensnake]

Ok, I guess, I may be a bit too pessimistic.

Still, why do I faintly recall having seen some quite messy indole
acylations? (low yields, purif nightmares) Prolly need to reseach
some lit.

Greensnake
An hour in library will save a week in laboratory.

[picloud]

What you definitely can do is run a Vilsmeir at the 3 position and make the formaldehyde.  Then one supposes the nitroalkene can be made and reduced to yield DMT?

Hey, navigation is slow for me at this (and some other) site.  Maybe as better browser would help until i can buy and inaugurate a new machine?  I'm running MS Explorer 5.  Any suggestions appreciated.
Cheers,

picloud

[Rhodium]

Reduction of the nitroethene from nitromethane and indole-3-carboxaldehyde would yield tryptamine, not DMT.