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Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxy-6-p-tolylpyridine is used as an intermediate in the synthesis of various pharmaceutical drugs. Its unique structure and functional groups make it a valuable building block for the development of new medications with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Methoxy-6-p-tolylpyridine is utilized as an intermediate for the production of agrochemicals. Its chemical properties allow it to be incorporated into the synthesis of compounds that can be used in crop protection, pest control, and other agricultural applications.
Used in Organic Synthesis:
2-Methoxy-6-p-tolylpyridine is employed as a key intermediate in organic synthesis, enabling the creation of a wide range of organic compounds. Its versatility and reactivity make it a valuable component in the synthesis of various organic molecules for research and industrial applications.

Upstream product

• 17228-64-7 6-chloro-2-methoxypyridine 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 149104-90-5 4-acetylphenylboronic acid 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 5720-05-8 4-methylphenylboronic acid 
• 106-38-7 para-bromotoluene 
• 32203-14-8 2,3-dihydro-2-(4-methylphenyl)benzo[d][1,3,2]diazaborinin-4(1H)-one 
• 90252-89-4 p-tolylzinc(II) chloride 

Relevant academic research and scientific papers

Sulfonated N-heterocyclic carbenes for Pd-catalyzed sonogashira and suzuki-miyaura coupling in aqueous solvents

The reactions of the N, N-diarylimidazolium and N, N-diarylimidazolinium salts with chlorosulfonic acid result in the formation of the respective disulfonated N-heterocyclic carbene (NHC) precursors in reasonable yields (46-77%). Water-soluble palladium catalyst complexes, in situ obtained from the respective sulfonated imidazolinium salt, sodium tetrachloropalladate (Na 2PdCl4) and potassium hydroxide (KOH) in water, were successfully applied in the copper-free Sonogashira coupling reaction in isopropyl alcohol/water mixtures using 0.2 mol% catalyst loading. The preformed (disulfonatedNHC)PdCl(cinnamyl) complex was used in aqueous Suzuki-Miyaura reactions at 0.1 mol% catalyst loading. The coupling protocol reported here is very useful for Sonogashira reactions of N- and 5-heterocyclic aryl bromides and chlorides with aryl- and alkylacetylenes.

Synthesis of substituted (N,C) and (N,C,C) Au(iii) complexes: the influence of sterics and electronics on cyclometalation reactions

Cyclometalated Au(iii) complexes are of interest due to their catalytic, medicinal, and photophysical properties. Herein, we describe the synthesis of derivatives of the type (N,C)Au(OAcF)2 (OAcF = trifluoroacetate) and (N,C,C)AuOAcF by a cyclometalation route, where (N,C) and (N,C,C) are chelating 2-arylpyridine ligands. The scope of the synthesis is explored by substituting the 2-arylpyridine core with electron donor or acceptor substituents at one or both rings. Notably, a variety of functionalized Au(iii) complexes can be obtained in one step from the corresponding ligand and Au(OAc)3, eliminating the need for organomercury intermediates, which is commonly reported for similar syntheses. The influence of substituents in the ligand backbone on the resulting complexes was assessed using DFT calculations,15N NMR spectroscopy and single-crystal X-ray diffraction analysis. A correlation between the electronic properties of the (N,C) ligands and their ability to undergo cyclometalation was found from experimental studies combined with natural charge analysis, suggesting the cyclometalation at Au(iii) to take place via an electrophilic aromatic substitution-type mechanism. The formation of Au(iii) pincer complexes from tridentate (N,C,C) ligands was investigated by synthesis and DFT calculations, in order to assess the feasibility of C(sp3)-H bond activation as a synthetic pathway to (N,C,C) cyclometalated Au(iii) complexes. It was found that C(sp3)-H bond activation is feasible for ligands containing different alkyl groups (isopropyl and ethyl), although the C-H activation is less energetically favored compared to a ligand containing tert-butyl groups.

Anthranilamide (aam)-substituted arylboranes in direct carbon-carbon bond-forming reactions

Anthranilamide (aam)-substituted arylboranes, which were reported to serve as masked boranes in the Suzuki-Miyaura coupling, have been found to be directly cross-coupled just by use of an aqueous medium. The excellent stability of 2-pyridyl-B(aam) toward protodeborylation allowed their smooth cross-coupling.

P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides

P,N,N-Pincer nickel complexes [Ni(Cl){N(2-R2PC6H 4)(2′-Me2NC6H4)}] (R = Ph, 3a; R = Pri, 3b; R = Cy, 3c) were synthesized and their catalysis toward the Kumada or Negishi cross-coupling reaction of aryl fluorides and chlorides was evaluated. Complex 3a effectively catalyzes the cross-coupling of (hetero)aryl fluorides with aryl Grignard reagents at room temperature. Complex 3a also catalyzes the cross-coupling of (hetero)aryl chlorides and arylzinc reagents at 80 °C with low catalyst loadings and good functional group compatibility. the Partner Organisations 2014.

Kumada coupling of aryl, heteroaryl, and vinyl chlorides catalyzed by amido pincer nickel complexes

A series of amido pincer complexes of nickel were examined for their catalysis in the Kumada cross-coupling reaction. The P,N,O-pincer nickel complexes tested are active catalysts for the cross-coupling of aryl, heteroaryl, and vinyl chlorides with aryl Grignard reagents. The reactions can proceed at room temperature and tolerate functional groups in aryl chlorides with the aid of LiCl and ZnCl2 additives (Figure presented).

Nanocrystalline titania-supported palladium(0) nanoparticles for Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides

The Suzuki cross-coupling reaction of various aryl and heteroaryl halides with arylboronic and heteroarylboronic acids was studied using a titania-supported palladium(0) catalyst at room temperature under air. The conversion and selectivity results obtained for many substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The methodology is similarly effective using 2-bromo-3,4,5-trimethoxybenzaldehyde as the coupling partner and gave products in good yield. Furthermore, it has been shown that it is useful for the synthesis of terphenyl and tetraphenyls. The catalyst is quantitatively recovered from the reaction by simple filtration and reused for a number of cycles without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture demonstrated that the palladium metal hardly leached into the solution within the limits of the detector (1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis. Copyright

Substituent-dependent structures and catalysis of benzimidazole-tethered N-heterocyclic carbene complexes of Ag(i), Ni(ii) and Pd(ii)

Homoleptic cationic benzimidazole-imidazolin-2-ylidene N-heterocyclic carbene (NHC = L) complexes of NiII and PdII have been prepared directly from the ligand precursor in salt form [H.L]Cl and from the transmetallation route via AgI. The N-tether of the imidazolinylidene ring imposes a significant influence on the nuclearity of the intermediate Ag(i)-NHC complexes and the geometric isomer outcome of the d8 products. Use of a benzyl-substituted NHC gives [Ag4(L Bn)2Cl4], 2a (from [HLBn]Cl, 1a, and Ag2O) (Bn = benzyl), which shows an alignment of four silver atoms bridged by the difunctional C-N ligands and chlorides. Its transmetallation with NiCl2(PPh3)4 and PdCl2(MeCN) 2 results in double-metal salts 2[M(LBn)2] 2+[Ag4Cl8]4- (M = Ni (3a) and Pd (4a)). The nuclearity of the Ag4 aggregate is maintained in the transmetallation process. Their Ag-free forms [M(LBn) 2]Cl2 (M = Ni (5) and Pd (6)) were prepared by direct deprotonation of 1a with M(OAc)2. The two carbenic carbon donor are cis- to each other in both 3a and 4a, thus imposing the weaker σ-benzimidazole nitrogen donor to be trans to them. A sterically demanding mesityl pendant however gives the dinuclear dissymmetic [Ag2(L Mes)2Cl2], 2b (Mes = mesityl) that shows a 12-membered metallomacrocyclic ring with a 2-coordinated [AgI(NHC) 2] and 4-coordinated [AgI(Imd)2Cl2] (Imd = imidazole). Transmetallation of the latter, or direct metallation from [HLMes]Cl, 1b, gives [M(LMes)2]Cl2 (M = Ni (3b) and Pd (4b)) with the two carbonic carbon trans to each other. The catalytic potential of 3b and 4b, which are more effective than 5 and 6, has been demonstrated by their high activities in Ni-catalyzed Kumada at room temperature and Pd-catalyzed Heck couplings of aryl and/or heteroaryl halides, respectively.

Highly efficient suzuki-miyaura coupling of heterocyclic substrates through rational reaction design

A dicyclohexyl(2-sulfo-9-(3-(4-sulfophenyl)propyl)-9H-fluoren-9-yl) phosphonium salt was synthesized in 64% overall yield in three steps from simple commercially available starting materials. The highly water-soluble catalyst obtained from the corresponding phosphine and [Na2PdCl4] enabled the Suzuki coupling of a broad variety of N- and S-heterocyclic substrates. Chloropyridines (-quinolines) and aryl chlorides were coupled with aryl-, pyridineor indoleboronic acids in quantitative yields in water/n-butanol solvent mixtures in the presence of 0.005-0.05 mol% of Pd catalyst at 100°C, chloropurines were quantitatively Suzuki coupled in the presence of 0.5 mol% of catalyst, and S-heterocyclic aryl chlorides and aryl- or 3-pyridylboronic acids required 0.01-0.05 mol % Pd catalyst for full conversion. The key to the high activity of the Pd-phosphine catalyst is the rational design of the reaction parameters (i.e., the presence of water in the reaction mixture, good solubility of reactants and catalyst in n-butanol/water (3:1), and the electron-rich and sterically demanding nature of the phosphine ligand).