Reactions of Aromatics (Arenes)

Aromatics (or arenes) undergo a variety of substitution reactions including Electrophilic Aromatic Substitution (EAS) and Nucleophilic Aromatic Substitution (NAS).  These reactions are useful in the synthesis of commodity chemicals, specialty chemicals, and pharmaceuticals.

An integral step in the synthesis of Imatinib is an Electrophilic aromatic substitution highlighted in green below.  This is known as a nitration reaction.

Imatinib, sold under the brand name Gleevec among others, is an oral chemotherapy medication used to treat cancer. Specifically, it is used for chronic myelogenous leukemia and acute lymphocytic leukemia that are Philadelphia chromosome-positive, certain types of gastrointestinal stromal tumors, hypereosinophilic syndrome, chronic eosinophilic leukemia, systemic mastocytosis, and myelodysplastic syndrome.