5-Bromo-N-(3,4-dimethoxybenzyl)pyridin-2-amine

The title compound, C14H15BrN2O2, an intermediate in drug discovery, was synthesized by the reaction of 5-bromopyridin-2-amine and 3,4-dimethoxybenzaldehyde. In the crystal, molecules are linked via pairs ofN—H⋯N hydrogen bonds, leading to the formation of inversion dimers. A short contact occurs between the aryl H atom (ortho position from N) and the centroid of the benzene ring.

The title compound, C 14 H 15 BrN 2 O 2 , an intermediate in drug discovery, was synthesized by the reaction of 5-bromopyridin-2-amine and 3,4-dimethoxybenzaldehyde. In the crystal, molecules are linked via pairs ofN-HÁ Á ÁN hydrogen bonds, leading to the formation of inversion dimers. A short contact occurs between the aryl H atom (ortho position from N) and the centroid of the benzene ring.

Related literature
For the anti-tumor activity of related compounds, see: Kovala-Demertzi et al. (2007). For the anti-ulcer activity of related compounds, see: Cho et al. (2001). For the anti-viral activity of related compounds, see: Mavel et al. (2002). For the antimicrobial activity of related compounds, see: Yeong et al. (2004).  Table 1 Hydrogen-bond geometry (Å , ).

Experimental
A methanol solution of 5-bromopyridin-2-amine (1.73 g, 0.01 mol), 3,4-dimethoxybenzaldehyde (1.66 g, 0.01 mol) with sodium cyanoborohydride (0.69 g, 0.011 mol) was heated to reflux for 3 h. The mixture was poured into cold water and then filtered to get this compound. Single crystals were obtained from the powder in ethanol after 5 days.

Refinement
H atoms were positioned geometrically (C-H = 0.95-0.99Å and N-H = 0.88Å) and refined using a riding model, with U iso (H) = 1.5U eq (C) for methyl groups and U iso (H) = 1.2U eq (C, N) for others.

Computing details
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009  The molecular structure of title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Special details Experimental. Absorption correction: CrysAlis Pro (Agilent Technologies, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq