673448-59-4

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 679794-95-7 3-trimethylsilylindazole 
• 271-44-3 benzimidazole 
• 5720-07-0 4-methoxyphenylboronic acid 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 

Downstream Products

• 942427-41-0 4-Indazol-1-yl-phenol 

Relevant academic research and scientific papers

Regioselective synthesis of 1-arylindazoles via N-arylation of 3-trimethylsilylindazoles

The copper(II)-catalyzed cross-coupling reaction of 3- trimethylsilylindazoles bearing substituents on the benzene ring with arylboronic acids regioselectively gave the corresponding 1-aryl-3- trimethylsilylindazoles and no 2-aryl isomers were formed at all. Moreover, the trimethylsilyl group of the resulting indazoles was easily removed by treatment with ethanolic KOH to give 1-arylindazoles.

Facile palladium-catalysed synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines

2-Bromobenzaldehydes react with arylhydrazines in toluene at 100°C in the presence of a catalytic amount of a palladium catalyst and phosphorus chelating ligands such as 1,1′-bis(diphenylphosphino)ferrocene and 1,3-bis(diphenylphosphino)propane along with NaO-t-Bu to afford 1-aryl-1H-indazoles in good yields.

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

Syntheses of 1-aryl-5-nitro-1h-indazoles and a general one-pot route to 1-aryl-1h-indazoles

An efficient route to substituted 1-aryl-1H-indazoles has been developed and optimized. The method involved the preparation of arylhydrazones from acetophenone or benzaldehyde substituted by fluorine at C2 and nitro at C5, followed by deprotonation and nucleophilic aromatic substitution (SNAr) ring closure in 45–90%. Modification of this procedure to a one-pot domino process was successful in the acetophenone series (73–96%), while the benzaldehyde series (63–73%) required a step-wise addition of reagents. A general one-pot protocol for 1-aryl-1H-indazole formation without the limiting substitution patterns required for the SNAr cyclization has also been achieved in 62–78% yields. A selection of 1-aryl-1H-indazoles was prepared in high yield by a procedure that requires only a single laboratory operation.

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

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

PHOTOREDOX-CATALYZED DIRECT C-H FUNCTIONALIZATION OF ARENES

The invention generally relates to methods of making substituted arenes via direct C-H amination. More specifically, methods of making para- and ortho-substituted arenes via direct C-H amination are disclosed. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Indazolium halides as efficient ligands for Pd-catalyzed Suzuki–Miyaura cross-coupling of aryl bromides with arylboronic acids

The indazolium halides containing various N-substituents have been conveniently prepared and applied in the palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl bromides with arylboronic acids at mild reaction conditions. The cross-coupling reaction provides the desired products in good to high yields. The ease of synthesis and the modularity, and the broad range of aryl bromides and arylboronic acids make this type of ligand attractive and promising for transition metal catalysis.

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.

Deproto-metallation using a mixed lithium-zinc base and computed CH acidity of 1-aryl 1H-benzotriazoles and 1-aryl 1H-indazoles

1-Aryl-1H-benzotriazoles and -1H-indazoles were synthesized, and their deproto-metallation using the base prepared by mixing LiTMP with ZnCl 2·TMEDA (1/3 equiv.) was studied. In the indazole series, reactions occurring at the 3 position were fo