You have the aryl bromide. You need the corresponding aniline. Buchwald-Hartwig isn’t working.
Been there. Done that. Got the t-shirt.
What to do? Check this out! A catalytic Ullman amination. No need for stochiometric amounts of copper. Ligand and solvent free. Table 3, entry 1, for instance.
JOC 2011, Article ASAP (Available here.)
Professor David Nichols, one of the World’s greatest authorities on novel psychoactive compounds, has just published an amazingly clear and honest column in the latest issue of Nature (doi:10.1038/469007a). Grab it here. It is a must-read.