92160-67-3

Upstream product

• 271-44-3 benzimidazole 
• 3076-56-0 p-tolyllead triacetate 
• 5720-05-8 4-methylphenylboronic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 539-44-6 N-4-methylphenylhydrazine 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 1373516-16-5 1-p-tolyl-1H-indazole-5-carbaldehyde 
• 253801-04-6 1H-indazole-5-carbaldehyde 
• 1416720-31-4 (1-p-tolyl-1H-indazol-5-yl)methanol 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 679794-95-7 3-trimethylsilylindazole 

Downstream Products

• 1429864-78-7 3-[4-(trifluoromethyl)phenyl]-1-(p-tolyl)-1H-indazole 
• 39602-11-4 3-methyl-1-(p-tolyl)quinazoline-2,4(1H,3H)-dithione 
• 39602-14-7 3-ethyl-1-(p-tolyl)quinazoline-2,4(1H,3H)-dithione 

Relevant academic research and scientific papers

A ligand-free copper-catalyzed strategy to the N-arylation of indazole using aryl bromides

A simple and efficient strategy for the C–N cross-coupling of indazole with a variety of substituted aryl bromides is reported. Under the optimized conditions, a broad scope of N-arylated products were obtained in good to excellent yields (up to 87%) under the ligand-free conditions.

Oxidant-Switched Palladium-Catalyzed Regioselective Mono- versus Bis-ortho-Aroylation of 1-Aryl-1H-indazoles with Aldehydes via C–H Bond Activation

A highly efficient oxidant-switched palladium-catalyzed regioselective C(sp2)–H/C(sp2)–H cross-dehydrogenative coupling (CDC) for direct mono/bis-ortho-aroylation of substituted 1-phenyl-1H-indazoles 1a–j with v

Access to 2-substituted-2: H -indazoles via a copper-catalyzed regioselective cross-coupling reaction

A CuCl catalyzed C-N cross-coupling reaction using commercially available 1H-indazoles with diaryliodonium salts is described. The methodology features ample structural versatility, affording 2-substituted-2H-indazole in good yields and complete N(2)-regiocontrol. Furthermore, the utility of the reaction was demonstrated in the synthesis of a known estrogen receptor β agonist. Mechanistic studies using density functional theory calculations suggested that the complete regioselectivity can be attributed to the only weak base TfO- in our system which could not deprotonate indazoles, and the catalyst oxidation process would be the rate-determining step.

Copper(I) Oxide/N,N′-Bis[(2-furyl)methyl]oxalamide-Catalyzed Coupling of (Hetero)aryl Halides and Nitrogen Heterocycles at Low Catalytic Loading

An easily prepared oxalic diamide is a powerful ligand for the copper-catalyzed coupling of aryl halides with nitrogen heterocycles. Only 1–2 mol% each of copper(I) oxide and N,N′-bis[(2-furyl)methyl]oxalamide (BFMO) are needed to form N-arylation products under mild conditions. More than 10 different types of nitrogen heterocycles are compatible with these conditions, thereby giving the corresponding N-arylation products. (Figure presented.).

A convenient and simple synthesis of N-arylpirrolopyrimidines using boronic acids and promoted by copper (II) acetate

A convenient and simple synthesis of novel N-arylated 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine using several aryl boronic acids and copper (II) acetate is described. The yields obtained for all derivatives are in the range of 45-70 % and this synthetic ap

A mild and regioselective Ullmann reaction of indazoles with aryliodides in water

A mild and regioselective Ullmann reaction of indazoles with aryliodides has been developed as a general method for the synthesis of 1-aryl-1H-indazoles. Water was used as the solvent wherein Tween 20 (2% w/w) was added to form aqueous micelles to improve

N-Picolinamides as ligands for Ullmann-type C-N coupling reactions

The use of N-phenyl-2-pyridincarboxamide-1-oxide as a ligand with Cu2O in Ullmann type C-N bond formations between aryl halides and N-heteroaryls in common solvents, such as MeCN, DMF, and DMSO at 82-120 °C has been successfully demonstrated. The ligand is effective when only 4% equiv is used relative to the substrate. The reaction provided the corresponding products in coupling of electron-rich, electron poor, and ortho-substituted aryl halides, including ortho aryl-chlorides, in good to very good yields. N-arylation is selectively preferred at the benzyl position when ortho-halide benzyl bromide is reacted with one equivalent of pyrazole. However, di-N-arylation is achieved in very high yields when 2.5 equiv of pyrazole is used, providing a stoichiometric control over the coupling reaction.

An efficient dehydroxymethylation reaction by a palladium catalyst

A general method for selective dehydroxymethylation has been discovered by using widely available Pd(OAc)2. The present study offers a new synthetic strategy for the regioselective functionalization by employing the steric, electronic and coordinating nature of the hydroxymethyl (-CH 2OH) group temporarily.

Copper(I) salt/PEG-400 catalysis in one-pot direct synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines

2-Bromobenzaldehydes are condensed and cyclized with arylhydrazines (or their hydrochlorides) in PEG-400 at 110 °C in the presence of a catalytic amount of a copper(I) salt along with a base to give 1-aryl-1H-indazoles in high yields. Copyright 2013 John Wiley & Sons, Ltd. Condensation of 2-bromobenzaldehydes with arylhydrazines (or their hydrochlorides) followed by C-N bond formation in PEG-400 in the presence of a copper(I) salt along with a base affords 1-aryl-1H-indazoles. Copyright

Copper powder-catalyzed C-N bond formation of arylhydrazones of 2-bromobenzaldehydes leading to 1-aryl-1 H-indazoles

Arylhydrazones of 2-bromobenzaldehydes and its analogs are cyclized in PEG-400 at 110C in the presence of a catalytic amount of copper powder along with NaOtBu to give 1-aryl-1H-indazole derivatives in good yields.