2′-Chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine

Dhafer Zinad,Dunya Al-Duhaidahaw,Ahmed Al-Amiery

doi:10.3390/m1040

Dhafer Zinad, Dunya Al-Duhaidahaw + Show 1 more

Open Access

https://doi.org/10.3390/m1040

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Journal: Molbank	Publication Date: Dec 22, 2018
Citations: 1	License type: CC BY 4.0

Affiliation: University of Technology- Iraq, University of Kufa

Abstract

The compound 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine was obtained with a good yield by the reaction of 2-chloro-4-(1-methyl-1H-imidazol-2-yl)pyridine with (2-chloropyridin-4-yl)boronic acid and structurally characterized by nuclear magnetic resonance (1H-NMR and 13C-NMR), thin-layer chromatography–mass spectrometry (TLC–MS), HPLC, gas chromatography–mass spectrometry (GC–MS), and elemental analysis. The functionalization of the pyridine was achieved by the palladium-catalyzed Suzuki–Miyaura carbon–carbon cross-coupling reaction that afforded the target compound.

Highlights

Introduction1. IntIrmodiduacztioolens are probably the most well-known heterocyclic compounds which are a common and iImpidoarztaonletsfeaarteupreroobfaablvyartiheetymoofsnt awtuerlal-lkpnroowdnuchtsetaenrodcmycelidciccionmalpaoguenndtss [w1–h3i]c.hBaerceauasecoomf mthoeinr aunndiqiumepaonrtaibnatcftearitaulreanodf aavnatirfiuetnygaolf nacatiuvriatileps,rothdeucitms iadnadzomleedciocrienasltraugcetnutrse[1h–a3s].aBttercaacutesde oaf hthuegire uinntieqrueestafnrtoibmaccthereimaliasntsdaasnatifsuignngaiflicaacntitvimtiesd,itchael ismcaifdfaozldole[4c–o6r]e
The desired compound was characterized by chemical analysis methods, which included nuclear magnetic resonance (NMR), liquid chromatography–mass spectrometry (LC–MS), gas chromatography–mass spectrometry (GC–MS), and elemental analysis
Nuclear magnetic resonance (NMR) data were obtained with a Bruker ARX NMR spectrometer (Bruker BioSpin AG, Faellanden, Switzerland) at 250 MHz and on a Bruker AVANCE III HD NMR spectrometer (Bruker BioSpin AG, Faellanden, Switzerland) at 300 MHz at ambient temperature

Summary

Introduction

1. IntIrmodiduacztioolens are probably the most well-known heterocyclic compounds which are a common and iImpidoarztaonletsfeaarteupreroobfaablvyartiheetymoofsnt awtuerlal-lkpnroowdnuchtsetaenrodcmycelidciccionmalpaoguenndtss [w1–h3i]c.hBaerceauasecoomf mthoeinr aunndiqiumepaonrtaibnatcftearitaulreanodf aavnatirfiuetnygaolf nacatiuvriatileps,rothdeucitms iadnadzomleedciocrienasltraugcetnutrse[1h–a3s].aBttercaacutesde oaf hthuegire uinntieqrueestafnrtoibmaccthereimaliasntsdaasnatifsuignngaiflicaacntitvimtiesd,itchael ismcaifdfaozldole[4c–o6r]e. Tidhaezreofloe–reb,iipnytrhidisinSheodretrNivoatteivaendwianscsoynntitnhuesaitzioend ofof rptrheveifoiursststtiumdeiebsy[1a0–p2a4ll]a, dainuemw-ciamtaidlyazzeodleS–ubzipuykrii–dMinieyadueraivcaatrivbeonw–acsarsbyonnthcersoizsse-dcofourptlhinegfirresat ctitmione b(Sycahepmalela1d)i.um-catalyzed Suzuki–Miyaura carbon–carbon cross-coupling reaction (Scheme 1). A chemo-selective coupling reaction proved to be important to carry out the reaction at 150 ◦C for 6 h to avoid by-products. Cesium carbonate was optimized as the base for the reaction. The desired compound was characterized by chemical analysis methods, which included nuclear magnetic resonance (NMR), liquid chromatography–mass spectrometry (LC–MS), gas chromatography–mass spectrometry (GC–MS), and elemental analysis. The purity of the target compound was examined using high-performance liquid chromatography (HPLC)

Materials and Methods

Conclusions