3-Bromoaniline → N-(3-Bromophenyl)-6-nitroquinazolin-4-amine

Participants

Reaction Steps

3-Bromoaniline is coupled with 4-chloro-6-nitroquinazoline, to produce 4-[(3-bromophenyl)amino]-6-nitroquinazoline, which is reduced thereafter to the corresponding 6-aminoquinazoline, as described. The 4-[(3-bromophenyl)amino]-6-aminoquinazoline is then reacted with bistributyltin, using tetrakis(triphenylphosphine)palladium in THF solution as the reaction catalyst, as is described hereinbelow. The stanylated quinazoline is then reacted with bromine-76 or bromine-77, in the presence of an oxidizing agent, to produce bromine-76 labeled or bromine-77 labeled 4-[(3-bromophenyl)amino]-6-aminoquinazoline, which is further reacted with 4-bromocrotonyl chloride (obtained by reacting oxalyl chloride and 4-bromocrotonic acid) and dimethylamine, as described, to yield the final bromine-76 labeled or bromine-77 labeled product.

Provenance & Evidence