How about reducing the aldehyde to the alcohol instead, to tryptophol? The tryptophol could then be reacted with tosyl chloride, and the tryptophol tosylate could then be reacted with a dialkylamine directly (or possibly cyanide or azide followed by reduction).
Would tosyl chloride attack the heterocyclic nitrogen?
http://rhodium.lycaeum.org (http://rhodium.lycaeum.org)
Lili: A while ago you promised to give a detailed writeup on how to go from indole to tryptophol to DMT via indolyl-MgBr. Do you have a heap of refs on the subject?
And is there any specific procedure to follow when brominating tryptophol, or is any PBr3 bromination protocol satisfactory?
http://rhodium.lycaeum.org (http://rhodium.lycaeum.org)
I'm afraid that the indole-3-acetaldehyde would polymerize under the acid or basic conditions needed for the Al/Hg reduction to work.
http://rhodium.lycaeum.org (http://rhodium.lycaeum.org)
A while ago you promised to give a detailed writeup on how to go from indole to tryptophol to DMT via indolyl-MgBr. Do you have a heap of refs on the subject?
Mee??
I never did it, but I would use 1 equiv. tryptophol and 0.4 - 0.5 equiv. PBr3 in absolutely dry THF or MeCN. At RT the reaction should be very fast. Work up by partitioning between water / CH2Cl2, washing with water, drying the organic phase with MgSO4, and evaporation.