N -[4-(1-Methyl-1 H -imidazol-2-yl)-2,4 (cid:48) -bipyridin-2 (cid:48) -yl]benzene-1,4-diamine

: N -[4-(1-Methyl-1 H -imidazol-2-yl)-2,4 (cid:48) -bipyridin-2 (cid:48) -yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2 (cid:48) -chloro-4-(1-methyl-1 H -imidazol-2-yl)-2,4 (cid:48) -bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized by chemical analysis, which includes nuclear magnetic resonance (NMR) ( 1 H-NMR and 13 C-NMR), Thin Layer Chromatography-Mass Spectrometry (TLC-MS), high-performance liquid chromatography (HPLC), Gas Chromatography-Mass Spectrometry (GC-MS), and elemental analysis.


Introduction
Imidazoles are an important and essential class of heterocyclic compounds and include many substances of both biological and chemical interest. In literature, research and applications of imidazole-based compounds have been rapidly developed and they involve a variety of broad potential applications as medicinal drugs, agrochemicals, human-made materials, artificial acceptors, supramolecular ligands, biomimetic catalysts, and so on [1][2][3]. Medicinal properties of imidazole-containing compounds comprise a broad spectrum of pharmacological activities, including anticancer, antimicrobial, antibacterial, antifungal, antioxidant, and anti-Parkinson activities [4][5][6]. Insertion of heterocyclic molecules, such as pyrazole and pyridine moieties in an imidazole, remains of great interest due to the broad applications of such heterocycles in the pharmaceutical and agrochemical industry [7]. In continuation of previous studies [8][9][10][11][12][13][14][15][16][17][18][19], a new imidazole-bipyridine derivative was synthesized for the first time, accomplished by a nucleophilic aromatic substitution (SNAr) reaction (Scheme 1).

Materials and Methods
All chemicals were purchased from commercial sources unless otherwise specified and were used without further purification. Thin-layer chromatography (TLC) reaction controls were performed for all reactions using fluorescent silica gel 60 F254 plates (Merck, Darmstadt, Germany) and visualized under natural light and UV illumination at 254 and 366 nm. The purity of the target compound was confirmed to be >95%, as determined by reversed-phase high-performance liquid chromatography (HPLC).
Nuclear magnetic resonance (NMR) data were obtained on a Bruker ARX NMR spectrometer (Bruker BioSpin AG, Faellanden, Switzerland) at 250 MHz, on a Bruker AVANCE III HD NMR spectrometer (Bruker BioSpin AG) at 300 MHz at ambient temperature. Chemical shifts are reported in parts per million (ppm) relative to tetramethylsilane (TMS). NMR Spectra are calibrated against the (residual proton) peak of the deuterated solvent used. A mass spectrum was recorded on an Advion expression S electrospray ionization mass spectrometer (ESI-MS) (Shimadzu Corporation, Kyoto, Japan) with TLC interface.

Materials and Methods
All chemicals were purchased from commercial sources unless otherwise specified and were used without further purification. Thin-layer chromatography (TLC) reaction controls were performed for all reactions using fluorescent silica gel 60 F254 plates (Merck, Darmstadt, Germany) and visualized under natural light and UV illumination at 254 and 366 nm. The purity of the target compound was confirmed to be >95%, as determined by reversed-phase high-performance liquid chromatography (HPLC).
Nuclear magnetic resonance (NMR) data were obtained on a Bruker ARX NMR spectrometer (Bruker BioSpin AG, Faellanden, Switzerland) at 250 MHz, on a Bruker AVANCE III HD NMR spectrometer (Bruker BioSpin AG) at 300 MHz at ambient temperature. Chemical shifts are reported in parts per million (ppm) relative to tetramethylsilane (TMS). NMR Spectra are calibrated against the (residual proton) peak of the deuterated solvent used. A mass spectrum was recorded on an Advion expression S electrospray ionization mass spectrometer (ESI-MS) (Shimadzu Corporation, Kyoto, Japan) with TLC interface.