2,3-dimethyl-6-nitro-2H-indazole

2,3-Dimethyl-6-nitro-2H-indazole is an impurity in the synthesis of Pazopanib (P210925) hydrochloride, an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

In the mol-ecule of 2,3-dimethyl-6-nitro-2H-indazole, C9H9N3O2, the indazole ring system is almost planar [maximum deviation = 0.019 (3) Å for the C atom bearing the nitro group]. In the crystal structure, inter-molecular C—H...O inter-actions link the mol-ecules into centrosymmetric dimers, forming R 2 2(18) ring motifs. Aromatic π–π contacts between indazole rings [centroid–centroid distances = 3.632 (1) and 3.705 (1)?] may further stabilize the structure[1].

[1] Yan Chen, Ping Wei, Zheng Fang. “2,3-Dimethyl-6-nitro-2H-indazole.” Acta crystallographica. Section E, Structure reports online 65 Pt 8 (2009): o1775.