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

Jie Li; Lin-Yan Lu; Wang-Xing Shen; Jian-You Shi

doi:10.1107/S1600536812015796

. 2012 Apr 18;68(Pt 5):o1405. doi: 10.1107/S1600536812015796

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

Jie Li ^a, Lin-Yan Lu ^a, Wang-Xing Shen ^a, Jian-You Shi ^b,^*

PMCID: PMC3344531 PMID: 22590293

Abstract

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.

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 anti-microbial activity of related compounds, see: Yeong et al. (2004 ▶).

Experimental

Crystal data

C₁₄H₁₅BrN₂O₂
M _r = 323.18
Monoclinic,
a = 6.3202 (2) Å
b = 13.7940 (4) Å
c = 15.8582 (6) Å
β = 100.961 (4)°
V = 1357.31 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.03 mm⁻¹
T = 130 K
0.42 × 0.30 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.509, T _max = 1.000
8188 measured reflections
2384 independent reflections
2055 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.060
S = 1.03
2384 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015796/rk2346sup1.cif

e-68-o1405-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015796/rk2346Isup2.hkl

e-68-o1405-Isup2.hkl^{(117.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015796/rk2346Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1ⁱ	0.88	2.31	3.090 (3)	149
C2—H2A⋯Cgⁱ	0.95	2.50	3.397 (3)	158

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

supplementary crystallographic information

Comment

The pyridine skeleton is a great importance to chemistry as well as biology which are well known for their versatile pharmacological activities such as anti-tumor (Kovala-Demertzi et al., 2007), anti-ulcer (Cho et al., 2001), anti-viral (Mavel et al., 2002) and antimicrobial (Yeong et al., 2004). The title compound is one of these compounds. The crystal packing is stabilized by a pair of strong intermolecular N2–H2···N1ⁱ classical hydrogen bonds conecting two moleculars to form a centrosymmtric dimer. The H2A atom from pyridine moiety has short contact (2.50Å) with Cgⁱ of phenyl ring (C7-C12). Symmetry code: (i) 1-x, 2-y, -z.

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.