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Chemokines (chemoattractant cytokines) together with their receptors represent key players in inflammatory processes. In order to develop novel chemokine CCR2 and CCR5 receptor antagonists, 2-benz-azepin-1-one  5  was prepared, which showed promising CCR2 affinity. During the synthesis, regioisomeric bromo substituted  β -keto esters  4a  and  4b  had to be separated. A crystal structure determination of the regioisomer  4b  displayed unequivocally the bromine atom in the 7-position and the existence of  4b  as the enol ester tautomer. Although the 7-membered azepine ring is rather flat, it is distorted around the 3-methylene moiety.

Molecular structure of a brominated 2-benzazepinone – a crucial intermediate in the synthesis of novel chemokine CCR2 receptor antagonists