6-Bromo­imidazo[1,2-a]pyridin-8-amine

Siham Dahmani; Youssef Kandri Rodi; Frederic Capet; El Mokhtar Essassi; Seik Weng Ng

doi:10.1107/S1600536811040177

. 2011 Oct 5;67(Pt 11):o2838. doi: 10.1107/S1600536811040177

6-Bromoimidazo[1,2-a]pyridin-8-amine

Siham Dahmani ^a, Youssef Kandri Rodi ^a, Frederic Capet ^b, El Mokhtar Essassi ^c, Seik Weng Ng ^d,^e,^*

PMCID: PMC3247577 PMID: 22219882

Abstract

The title compound, C₇H₆BrN₃, crystallizes with three independent molecules in the asymmetric unit. The molecules are approximately planar (r.m.s. deviations for all non-H atoms = 0.016, 0.023 and 0.024 Å). The primary amine groups show pyramidal coordination. In the crystal, adjacent molecules are linked by N—H⋯N hydrogen bonds. For two independent molecules, the amine groups are hydrogen-bond donors via one H atom to one acceptor atom, whereas for the third independent molecule, the amine group is a hydrogen-bond donor to two acceptor atoms.

Related literature

For background information on 8-amino-6-bromo-imidazo[1,2-a]pyridine, see: Dwyer et al. (2007 ▶).

Experimental

Crystal data

C₇H₆BrN₃
M _r = 212.06
Monoclinic,
a = 15.1378 (5) Å
b = 21.2006 (8) Å
c = 6.9744 (3) Å
β = 92.6106 (7)°
V = 2235.97 (15) Å³
Z = 12
Mo Kα radiation
μ = 5.44 mm⁻¹
T = 100 K
0.13 × 0.04 × 0.02 mm

Data collection

Bruker APEX DUO diffractometer
Absorption correction: multi-scan SADABS (Sheldrick, 1996 ▶)’ T _min = 0.538, T _max = 0.899
44729 measured reflections
5538 independent reflections
4675 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.078
S = 1.08
5538 reflections
322 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.15 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040177/bt5659sup1.cif

e-67-o2838-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040177/bt5659Isup2.hkl

e-67-o2838-Isup2.hkl^{(271.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040177/bt5659Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯N5	0.88 (1)	2.16 (1)	3.034 (3)	169 (4)
N6—H61⋯N2	0.88 (1)	2.23 (1)	3.094 (3)	168 (3)
N9—H91⋯N8ⁱ	0.87 (1)	2.27 (2)	3.091 (3)	158 (3)
N9—H92⋯N6ⁱⁱ	0.88 (1)	2.27 (1)	3.143 (3)	177 (3)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We thank Université MohammedV-Agdal, Université Sidi Mohammed Ben Abdallah and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

8-Amino-6-bromo-imidazo[1,2-a]pyridine (Scheme I) was recently evaluated for its as a cyclin-dependent kinase-2 (CDK2) inhibitor (Dwyer et al., 2007). We have synthesized the compound for use in a similar study. The non-H atoms of the three independent molecules of C₇H₆BrN₃ are planar (Fig. 1). Their primary amino groups show pyramidal coordination, and adjacent molecules are linked by N–H···N hydrogen bonds to form a layer structure. For two independent molecules, their amino groups are each a hydrogen-bond donor to one acceptor atom whereas for the third independent molecule, its amino group is hydrogen-bond bond to two acceptor atoms (Table 1).

Experimental

A mixture of chloroacetaldehyde (0.68 ml, 10.6 mmol), 5-bromo-2,3-diaminopyridine (1 g, 5.32 mmol) and sodium bicarbonate (0.44 g, 5.32 mmol) in ethanol (10 ml) was heated. The reaction was monitored by TLC. On completion of the reaction, the solution was extracted with dichloromethane and the organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent followed by recrystallization from hexane gave yellow crystals of the title compound.