2-(1H-Imidazol-1-yl)-4-[3-(trifluoro­meth­yl)phen­yl]-1,3-thia­zole

Konstantin V Kudryavtsev; Andrei V Churakov; Jih-Hwa Guh

doi:10.1107/S1600536813000615

. 2013 Jan 16;69(Pt 2):o238. doi: 10.1107/S1600536813000615

2-(1H-Imidazol-1-yl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole

Konstantin V Kudryavtsev ^a,^b,^*, Andrei V Churakov ^c, Jih-Hwa Guh ^d

PMCID: PMC3569771 PMID: 23424517

Abstract

The title compound, C₁₃H₈F₃N₃S, consists of three linked aromatic rings. The whole molecule (except for the three F atoms) is planar to within 0.225 (2) Å. In the crystal, adjacent molecules are linked into chains along the ac diagonal by weak C—H⋯N interactions.

Related literature

For general background to the synthesis of imidazolothiazoles by copper-catalysed coupling, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C₁₃H₈F₃N₃S
M _r = 295.28
Monoclinic,
a = 8.4152 (7) Å
b = 19.2403 (15) Å
c = 8.4105 (7) Å
β = 114.210 (1)°
V = 1241.98 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 150 K
0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.893, T _max = 0.972
9797 measured reflections
2716 independent reflections
2164 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.103
S = 1.07
2716 reflections
213 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Click here for additional data file.^{(21.3KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000615/ff2095sup1.cif

e-69-0o238-sup1.cif^{(21.3KB, cif)}

Click here for additional data file.^{(133.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000615/ff2095Isup2.hkl

e-69-0o238-Isup2.hkl^{(133.4KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000615/ff2095Isup3.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
C9—H9⋯N3ⁱ	0.95 (2)	2.34 (2)	3.278 (2)	169.4 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This study was partially supported by the Russian Foundation for Basic Research (project Nos. 11–03-00630_a and 12–03-92005-NSC_a) and by the National Science Council of the Republic of China (NSC101–2923-B-002–008-MY3).

supplementary crystallographic information

Comment

The title compound, C₁₃H₈F₃N₃S, which is a potential anticancer agent, consists of the three linked aromatic and heteroaromatic cycles, which were condensed by copper-catalyzed method (Fig. 1). The whole molecule (except three fluorine atoms) is planar within 0.225 (2) Å (Fig. 2).

In the crystal, the adjacent molecules are combined in chains along ac-diagonal by weak C—H···N interactions (Fig. 3). The C···N separation is equal to 3.278 (2) Å and C—H···N angle is close to linear (169 (2) °).

Experimental

2-Bromo-4-(3-(trifluoromethyl)phenyl)thiazole (0.800 g, 2.60 mmol) was added to a stirred suspension of imidazole (0.345 g, 5.07 mmol), CuI (0.209 g, 1.10 mmol) and Cs₂CO₃ (1.830 g, 5.62 mmol) in 30 ml of DMF under argon atmosphere. The reaction mixture was stirred for 8 h at rt and then for 7 h at 115 °C. After cooling to the ambient temperature the reaction mixture was filtered and precipitate was washed with 30 ml of DMF. The solution was concentrated under vacuum and residue was diluted with 80 ml of ethyl acetate. Organic phase was washed with water (2 x 10 ml) and saturated solution of NH₄Cl (1 x 10 ml), dried over Na₂SO₄, concentrated and purified by column chromatography on silica gel 60 (particle size 0.040–0.063 mm) using CHCl₃—MeOH (gradient from 1:0 to 50:1) as eluent. 2-(1H-Imidazol-1-yl)-4-(3-(trifluoromethyl)phenyl)thiazole, yield 368 mg (48%), yellowish crystals, mp 99–100°C. ¹H NMR (400 MHz, CDCl₃/DMSO-d₆ 5:1): δ 7.16 (s, 1H), 7.52–7.56 (m, 2H), 7.67 (s, 1H), 7.75 (s, 1H), 8.09–8.11 (m, 1H), 8.15 (s, 1H), 8.40 (s, 1H). ¹³C NMR (100 MHz, CDCl₃/DMSO-d₆ 5:1): δ 111.88, 118.24, 122.95, 122.98, 125.00, 125.03, 129.59, 129.66, 130.17, 130.62, 134.35, 135.63, 150.89, 157.05. Found, %: C, 52.95; H, 2.69; N, 14.20. C₁₃H₈F₃N₃S. Calculated, %: C, 52.88; H, 2.73; N, 14.23. The crystals were obtained by slow evaporation of the CDCl₃/DMSO-d₆ (5:1) solution.