4838-00-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Methylindazole is used as a building block for the synthesis of various active pharmaceutical ingredients due to its versatile chemical structure and potential pharmacological properties.
Used in Organic Synthesis:
2-Methylindazole is used as a key intermediate in the synthesis of organic compounds, contributing to the development of new chemical entities with potential applications in various fields.
Used in Coordination Chemistry:
2-Methylindazole is used as a ligand in the formation of complexes with transition metal ions, which is valuable in the study and application of coordination chemistry.
Used in Drug Development:
2-Methylindazole is used as a pharmacological agent, particularly for its role as an antagonist of histamine receptors, which may have therapeutic applications in treating conditions related to histamine activity.

InChI:InChI=1/C8H8N2/c1-10-6-7-4-2-3-5-8(7)9-10/h2-6H,1H3

Upstream product

• 271-44-3 benzimidazole 
• 74-88-4 methyl iodide 
• 26429-63-0 1,2-Dimethylindazolium iodide 
• 23300-99-4 1-tosyl-1H-indazole 
• 124-41-4 sodium methylate 

Downstream Products

• 13436-49-2 1-acetylindazole 
• 26429-63-0 1,2-Dimethylindazolium iodide 
• 457891-25-7 3-bromo-2-methyl-2H-indazole 
• 125923-19-5 1-benzoyl-2,3-dihydro-2-methylindazole-3-carbonitrile 
• 34252-47-6 3-(α-hydroxybenzyl)-2-methylisoindazole 
• 109216-61-7 3-methoxycarbonyl-2-methylisoindazole 
• 50407-18-6 2,3-Dimethylindazol 
• 49572-64-7 3-iodo-2-methyl-2H-indazole 
• 89215-26-9 2-methyl-3-phenyl-2H-indazole 
• 51093-42-6 1‐methyl‐3‐phenyl‐1H‐indazole 

Relevant academic research and scientific papers

Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

Alkylation of 4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (1b) with iodomethane in THF using NaHMDS as base selectively provided N2-methyl product 4-methoxy-2-methyl-2H-pyrazolo[3,4-d]pyrimidine (3b) in an 8/1 ratio over N1-methyl product (2b). Interestingly, conducting the reaction in DMSO reversed selectivity to provide a 4/1 ratio of N1/N2 methylated products. Crystal structures of product 3b with N1 and N7 coordinated to sodium indicated a potential role for the latter reinforcing the N2-selectivity. Limits of selectivity were tested with 26 heterocycles which revealed that N7 was a controlling element directing alkylations to favor N2 for pyrazolo- and N3 for imidazo- and triazolo-fused ring heterocycles when conducted in THF. Use of 1H-detected pulsed field gradient-stimulated echo (PFG-STE) NMR defined the molecular weights of ionic reactive complexes. This data and DFT charge distribution calculations suggest close ion pairs (CIPs) or tight ion pairs (TIPs) control alkylation selectivity in THF and solvent-separated ion pairs (SIPs) are the reactive species in DMSO.

Direct N-Alkylation and Kemp Elimination Reactions of 1-Sulfonyl-1H-Indazoles

The reactions of 1-sulfonyl-1H-indazoles under basic conditions are discussed, and the direct N-alkylation and Kemp elimination reactions of these compounds are reported. A series of 2-(p-tosylamino)benzonitriles and N-alkyl indazoles were prepared in good yields. Moreover, the 2-(p-tosylamino)benzonitriles could be transformed into a diverse range of important derivatives in a one-pot reaction. This method was successfully applied to the total syntheses of quindolinone and cryptolepinone; quindolinone was prepared in a one-pot reaction from 1-sulfonyl-1H-indazole.

Direct C-H Alkenylation of Functionalized Pyrazoles

We have developed inter- and intramolecular C-H alkenylation reactions of pyrazoles. The catalyst, derived from Pd(OAc)2 and pyridine, enabled the oxidative alkenylation of pyrazoles containing a variety of functional groups at the C4 position.

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.

Novel synthesis of indazoles from (η6-arene)tricarbonylchromium complexes

Indazole chromium complexes and some of its derivatives were synthesised by two strategies: (1) by cyclisation of [η 6-2-(2′-phenylhydrazine)-1,3-dioxolane]tricarbonylchromium (2) in acidic conditions which was converted into σ-complex (11); (2) by thermolysis of Cr(CO)6 with 1-bis(trimethylsilyl)methylindazole (3) and 2-bis(trimethylsilyl)methyl-3-trimethyl-silylindazole (4), using bulky protecting groups at N(1) or simultaneously at N(2) and C(3), to afford [η6-1-bis(trimethylsilyl)methylindazole]tricarbonylchromium (14) and [η 6-2-bis(trimethylsilyl)methyl-3-trimethylsilylindazole] tricarbonylchromium (15), respectively. The deprotonation of complex 14 followed by electrophilic quench occurs at the C(4) and C(7) positions in a ratio of 3:1 and with complex 15 the deprotonation was completely regioselective at the C(7) position. The position of this substitution was confirmed by n.O.e. difference spectroscopy and X-ray crystal structure determination of the [η 6-2-bis(trimethylsilyl)methyl-7-methyl-3-trimethylsilylindazole] tricarbonylchromium (5). These complexes were decomplexed to produce new substituted indazole derivatives in good yield.