[limpet chicken]

Does anyone happen to have any refs for proecdures involving methoxylation of a 5-position hydroxy group on an indole ring?

I am contemplating the use of methanolic sodium ethoxide, any better ideas?

[movies]

Starting from 5-hydroxy indole?  Methanol won't work for that.  You need something like methyl iodide or dimethyl sulfate.

[limpet chicken]

I was actually after methoxylation, not methylation, MeI cannot possibly do that, did you MEAN to use MeI/di-MeSO4.

I am actually working with tryptamines, rather than indole itself, as the tryptamines are more available (serotonin, melatonin, mexamine,), indole itself is a b$*%( to actually come by these days.

I wanted to prepare mexamine (5-MeO-T), starting from serotonin, and perhaps prepare melatonin from the formed mexamine, although I could always buy melatonin, and decarboxylate it with CaO/NaOH to yield mexamine.