Hey Guys,
I've been trying to methylate my substrate* by pre-mixing it with methyl iodide in DCM, and slowly adding base at low temp. The problem is the deprotonated compound can go down an elimination pathway to form a better electrophile than MeI and I keep getting polymerized scum for my efforts. The same reaction conditions do work if I use something like acetic anhydride as the electrophile, so it is possible to modify this thing with electrophiles, but methylation has been a dud so far.
So my question is: Is it worth the risk to make some methyl trifluorosulfonate, or does someone have a sure-fire methylation protocol they always fall back on?
So far I've tried altering the base (the usual non-nucleophilic classics), the solvent, and the temp.
*It's the nitrogen in a rather crazy amide if you must know, and no, I can't start with it pre-methylated. I'd tell you more if I could. You know how it is...