465529-56-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5-BROMO-2-METHYL-2H-INDAZOLE is used as a key building block for the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of new compounds with desired properties, contributing to the development of innovative treatments and products in these industries.
Used in Dye and Pigment Production:
5-BROMO-2-METHYL-2H-INDAZOLE is utilized in the production of dyes and pigments due to its chemical properties. Its ability to be modified and react with other compounds makes it a valuable component in creating a wide range of colorants for various applications.
Used in Medicinal Chemistry Research:
5-BROMO-2-METHYL-2H-INDAZOLE has potential applications in the field of medicinal chemistry, where it can be used for the development of new drugs and therapeutic agents. Its structure and properties make it an attractive candidate for further research and exploration by scientists and industry professionals.
Used in Organic Synthesis and Chemical Manufacturing:
As a versatile building block, 5-BROMO-2-METHYL-2H-INDAZOLE is employed in organic synthesis and chemical manufacturing processes. Its adaptability in chemical reactions and modifications enables the creation of new compounds with specific properties, making it a valuable resource in the development of novel materials and products.

InChI:InChI=1/C8H7BrN2/c1-11-5-6-4-7(9)2-3-8(6)10-11/h2-5H,1H3

Upstream product

• 53857-57-1 5-bromo-1H-indazole 
• 74-88-4 methyl iodide 
• 40598-76-3 3,5-dibromoindazole 
• 465529-55-9 5-bromo-2H-indazole 
• 74-83-9 methyl bromide 
• 20357-20-4 5-bromo-2-nitrobenzaldehyde 
• 74-89-5 methylamine 
• 914311-53-8 5-bromo-2-fluoro-benzaldehyde O-methyl-oxime 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 40598-94-5 3-bromo-1H-indazole 
• 861796-22-7 acetic acid-(4-bromo-2-methyl-N-nitroso-anilide) 
• 24106-05-6 4'-bromo-2'-methylacetanilide 

Downstream Products

• 1189746-27-7 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole 
• 1823787-20-7 2‐(5‐bromo‐2‐methyl‐2H‐indazol‐3‐yl)propan‐2‐ol 
• 1619903-54-6 trans‐N1‐{4‐[2‐methyl‐3‐(propan‐2‐yl)‐2H‐indazol‐5‐yl]pyrimidin‐2‐yl}‐N4‐(oxan‐4‐yl)cyclohexane‐1,4‐diamine 
• 1619903-55-7 N₁-[4-(3-isopropyl-2-methyl-2H-indazol-5-yl)pyrimidin-2-yl]-N₄-(tetrahydro-2H-pyran-4-yl)cyclohexane-trans-1,4-diamine methanesulfonic acid salt 
• 952319-71-0 (2-methyl-2H-indazol-5-yl)boronic acid 

Relevant academic research and scientific papers

Discovery of N-(4-(3-isopropyl-2-methyl-2 H-indazol-5-yl)pyrimidin-2-yl)-4-(4-methylpiperazin-1-yl)quinazolin-7-amine as a Novel, Potent, and Oral Cyclin-Dependent Kinase Inhibitor against Haematological Malignancies

Hematologic malignancies (HM) start in blood forming tissue or in the cells of the immune system. Cyclin-dependent kinases (CDKs) regulate cell cycle progression, and some of them control cellular transcription. CDK inhibition can trigger apoptosis and could be particularly useful in hematological malignancies. Herein, we describe our efforts toward the discovery of a novel series of quinazoline derivatives as CDK inhibitors. Intensive structural modifications lead to the identification of compound 37d as the most active inhibitors of CDKs 1, 2, 4, 8 and 9 with balancing potency and selectivity against CDKs. Further biological studies revealed that compound 37d can arrest the cell cycle and induce apoptosis via activating PARP and caspase 3. More importantly, compound 37d showed good antitumor efficacy in multiple HM mice xenograft models with no obvious toxicity. These results indicated that CDK 1, 2, 4, 8, and 9 inhibitors could be potentially used to treat certain hematologic malignancies.

HETEROBICYCLIC COMPOUNDS FOR INHIBITING THE ACTIVITY OF SHP2

A compound of formula (I):wherein Ring A, Q, R1,R2, R3, R4, R5, R6, R7, R8, R9, R10, R11,X, a,b, c and d are as defined in the specification.

SUBSTITUTED AMIDE COMPOUNDS USEFUL AS FARNESOID X RECEPTOR MODULATORS

Disclosed are compounds of Formula (I): or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt or solvate thereof, wherein Q is: (i) halo, cyano, hydroxyl, NRxRx, C(O)OH, C(O)NH2, C1-6 alkyl substituted with zero to 6 R1a, or P(O)R1cR1c; or (ii) L R1; and A, X1, X2, X3, X4, Z1, Z2, R1, R1a, R1c, R2, R3a, R3b, Rx, L, a, b, and d are defined herein. Also disclosed are methods of using these compounds to modulate the activity of farnesoid X receptor (FXR); pharmaceutical compositions comprising these compounds; and methods of treating a disease, disorder, or condition associated with FXR dysregulation, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.

SUBSTITUTED AMIDE COMPOUNDS USEFUL AS FARNESOID X RECEPTOR MODULATORS

Disclosed are compounds of Formula (I) or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt or solvate thereof, wherein Q is a 5-membered heterocyclyl or 5-membered heteroaryl having 1 to 4 heteroatoms independently selected from N, O, and S, substituted with zero to 4 R1; and A, X1, X2, X3, X4, Z1, Z2, R1, R2, R3a, R3b, a, b, and d are defined herein. Also disclosed are methods of using these compounds to modulate the activity of farnesoid X receptor (FXR); pharmaceutical compositions comprising these compounds; and methods of treating a disease, disorder, or condition associated with FXR dysregulation, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.

CRYSTAL FORM, SALT TYPE OF SUBSTITUTED 2-HYDRO-PYRAZOLE DERIVATIVE AND PREPARATION METHOD THEREFOR

A crystal form and a salt type of a substituted 2-hydro-pyrazole derivative, preparation method therefor, and use of the crystal form and the salt type in preparation of a medicament for treating cancers such as breast cancer, lung cancer and the like.

SUBSTITUTED 2-HYDROGEN-PYRAZOLE DERIVATIVE SERVING AS ANTICANCER DRUG

Disclosed is a substituted 2H-pyrazole derivative serving as a selective CDK4/6 inhibitor. Specifically, disclosed is a compound of formula (I) or a pharmaceutically acceptable salt thereof which serves as a selective CDK4/6 inhibitor.

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.

Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and stereospecific cyclic adducts.

2-H-INDAZOLE DERIVATIVES AS CYCLIN-DEPENDENT KINASE (CDK) INHIBITORS AND THERAPEUTIC USES THEREOF

Indazole compounds of formula (I) as cyclin-dependent kinase (CDK) and cellproliferation inhibitors, and therapeutic uses and methods of preparation thereof, are disclosed. These compounds, and pharmaceutically acceptable salts, solvates, prodrugs, and pharmaceutical compositions thereof, are useful for treating diseases and disorders associated with activity of cyclin-dependent kinases, in particular CDK4/6, including but not limited to various cancers and inflammation-related diseases or conditions:

SUBSTITUTED QUINOXALINE DERIVATIVES

The present invention relates to substituted quinoxaline derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.