6-Bromo-2-(4-methoxyphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

Abstract

In the title compound, C 14 H 12 BrN 3 O, the dihedral angle between the mean planes of the imidazo [4,5-b]pyridine ring system and the methoxyphenyl ring is 41.53 (12) . In the crystal, weak C-HÁ Á ÁN hydrogen bonds link the molecules into chains along the c-axis direction. Weak -stacking interactions involving the imidazole and the methoxyphenyl rings further stabilize the crystal packing. Structure descriptionDerivatives of imidazopyridine exhibit several remarkable pharmacological activities. For example they are used as antiviral (Scribner et al. 2007), antibacterial (Liang et al. 2007) and anti-neuroinflammatory agents (Ock et al., 2010). As a continuation of our research on the development of substituted imidazo [4,5-b]pyridine derivatives (Bourichi et al., 2017), we report here the synthesis and structure of a new imidazo [4,5-b]pyridine derivative synthesized by the reaction of methyl iodide and 6-bromo-2-(4-methoxyphenyl)-3H-imidazopyridine in the presence of a catalytic quantity of tetra-n-butylammonium bromide under phase transfer catalysis conditions.The title compound crystallizes with one independent molecule in the asymmetric unit (Fig. 1). The molecule is slightly twisted, as is evident from the dihedral angle of 41.53 (12) between the mean planes of the imidazo [4,5-b]pyridine ring system and the methoxyphenyl ring. In the crystal, a single weak C13-H13CÁ Á ÁN1 intermolecular interaction links the molecules into chains along the c-axis direction (Table 1, Fig. 2). In addition, weak -stacking interactions involving the imidazole and the methoxyphenyl rings further stabilize the crystal packing [intercentroid distance, Cg1Á Á ÁCg3 ii =