3-[2-(6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)eth­yl]-1,3-oxazolidin-2-one

Younes Ouzidan; Jerry P Jasinski; Raymond J Butcher; James A Golen; El Mokhtar Essassi; Lahcen El Ammari

doi:10.1107/S1600536811012669

. 2011 Apr 13;67(Pt 5):o1095. doi: 10.1107/S1600536811012669

3-[2-(6-Bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)ethyl]-1,3-oxazolidin-2-one

Younes Ouzidan ^a,^*, Jerry P Jasinski ^b, Raymond J Butcher ^c, James A Golen ^b, El Mokhtar Essassi ^d, Lahcen El Ammari ^e

PMCID: PMC3089183 PMID: 21754415

Abstract

In the title molecule, C₁₇H₁₅BrN₄O₂, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.015 (2) Å, and forms dihedral angles of 37.8 (2) and 35.5 (2)° with the phenyl and oxazolidine rings, respectively. The conformation adopted by the molecule is stabilized by an intramolecular π⋯π interaction [centroid–centroid distance = 3.855(2) Å] between oxazolidine and phenyl rings. The crystal packing features intermolecular C—H⋯N and C—H⋯O interactions.

Related literature

For background to the medicinal chemistry of oxazolidin-2-ones and their application in asymmetric synthesis, see: Diekema & Jones (2000 ▶); Mukhtar & Wright (2004 ▶); Evans et al. (1993 ▶); Matsunaga et al. (2005 ▶). For similar compounds with an imidazo[4,5-b]pyridine group, see: Ouzidan et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₅BrN₄O₂
M _r = 387.24
Monoclinic,
a = 11.3553 (6) Å
b = 11.5915 (5) Å
c = 12.2542 (8) Å
β = 98.685 (6)°
V = 1594.46 (15) Å³
Z = 4
Mo Kα radiation
μ = 2.60 mm⁻¹
T = 170 K
0.22 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction XcaliburE Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.599, T _max = 0.652
7850 measured reflections
3791 independent reflections
2839 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.091
S = 1.03
3791 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012669/gk2362sup1.cif

e-67-o1095-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012669/gk2362Isup2.hkl

e-67-o1095-Isup2.hkl^{(185.9KB, hkl)}

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
C4—H4A⋯N2ⁱ	0.95	2.61	3.544 (3)	168
C10—H10A⋯N2ⁱⁱ	0.99	2.55	3.261 (3)	128
C15—H15A⋯O1ⁱⁱⁱ	0.95	2.53	3.423 (3)	156

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

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Oxazolidin-2-ones are a very important class of heterocyclic compounds and their derivatives have attracted attention in various areas of drug development for antibacterial activity (Diekema & Jones, 2000; Mukhtar & Wright, 2004). Some oxazolidin-2-ones have been used as chiral auxiliaries in a wide range of asymmetric reactions (Evans et al.,1993; Matsunaga et al., 2005). As a continuation of our research works devoted to the development of substituted imidazo[4,5-b]pyridine derivatives (Ouzidan et al., 2010a,b), we report in this paper the synthesis of a new 2,6-disubstituted imidazo[4,5-b]pyridine possessing the oxazolidin-2-one ring (Scheme 1) by the action of bis(2-chloroethyl)amine hydrochloride on 6-bromo-2-phenyl-3H-imidazo [4,5-b]pyridine in boiling DMF.

The title molecule is shown in Fig. 1. The two cycles forming the imidazo[4,5-b]pyridine are almost planar with a maximum deviation of 0.015 (1) Å for N3 atom and form dihedral angles of 37.8 (2)° and 35.5 (2)° with the phenyl and the oxazolidine rings respectively. The oxazolidinone group is linked to the phenyl group by a weak intramolecular C-H···π interaction. The crystal structure is stabilized by two intermolecular C–H···N and C–H···O interactions as shown in Fig. 2 and Table 2.

Experimental

To 6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridine (0.3 g, 1.09 mmol), potassium carbonate (0.33 g, 2.4 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.1 mmol) in DMF (15 ml) was added bis(2-chloroethyl)amine hydrochloride (0.23 g, 1.31 mmol). The mixture was heated for 48 h. After the completion of the reaction (as monitored by TLC), the inorganic salt was filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel by using (ethanol/ethyl acetate: 1/4) as eluent. The product was recrystallized from ethanol to furnish colourless crystals (m.p. 454 K).