156454-43-2

Basic information

• Product Name: 5-BROMO-7-METHYL-1H-INDAZOLE
• Synonyms: 5-BROMO-7-METHYL-1H-INDAZOLE;TIMTEC-BB SBB002553;1H-Indazole, 5-bromo-7-methyl-
• CAS NO: 156454-43-2
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.06
• Product Categories: Halogenated Heterocycles;Heterocyclic Building Blocks;Indazoles
• Mol File: 156454-43-2.mol

Chemical Properties

• Melting Point: 184-185°C
• Boiling Point: 346.22 °C at 760 mmHg
• Flash Point: 163.188 °C
• Appearance: /
• Density: 1.655 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.13±0.40(Predicted)
• CAS DataBase Reference: 5-BROMO-7-METHYL-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-7-METHYL-1H-INDAZOLE(156454-43-2)
• EPA Substance Registry System: 5-BROMO-7-METHYL-1H-INDAZOLE(156454-43-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 156454-43-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-7-METHYL-1H-INDAZOLE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
5-BROMO-7-METHYL-1H-INDAZOLE is used as a building block in the development of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can lead to the creation of more effective and targeted products for agricultural use.
The exact physical or chemical properties of 5-BROMO-7-METHYL-1H-INDAZOLE, such as boiling point, melting point, toxicity, or color, can vary widely depending on its state, preparation method, or storage circumstances. This variability highlights the importance of understanding the specific context in which 5-BROMO-7-METHYL-1H-INDAZOLE is being used to ensure its effectiveness and safety.

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

Upstream product

• 1424621-40-8 C₁₂H₁₇BrN₂ 
• 24596-19-8 4-bromo-2,6-dimethylphenylamine 
• 943145-68-4 trans-4-bromo-2,6-dimethylphenyldiazo-tert-butyl sulfide 

Downstream Products

• 1414976-16-1 4-((7-methyl-1H-indazol-5-yl)methylene)-2-phenyloxazol-5(4H)-one 
• 1414976-17-2 methyl 2-benzamido-3-(7-methyl-1H-indazol-5-yl)-acrylate 
• 635712-41-3 C₂₀H₁₉N₃O₄ 
• 1146637-10-6 5-bromo-2,7-dimethyl-2H-indazole 
• 1613505-05-7 7-methyl-5-(2-(trifluoromethyl)phenyl)-1H-indazole 
• 1197938-68-3 2'-cyclohexyl-1-(7-methyl-1H-indazole-5-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one 
• 1197938-59-2 2'-benzyl-1-(7-methyl-1H-indazole-5-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one 
• 1031417-41-0 7-methyl-1H-indazole-5-carboxylic acid 
• 635712-40-2 7-methyl-1H-indazole-5-carbaldehyde 

Relevant articles and documents

A Novel Approach to 1H-Indazoles via Arylazosulfides

Treatment of variously substituted (o-alkylaryl)azosulfides 1a-n with potassium tert-butoxide in DMSO at room temperature smoothly furnishes 1H-indazoles 2a-n.

PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT FACTOR D MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement factor D or a pharmaceutically acceptable salt or composition thereof are provided. The inhibitors described herein target factor D and inhibit or regulate the complement cascade. The inhibitors of factor D described herein reduce the excessive activation of complement.

AUTOTAXIN INHIBITORS AND USES THEREOF

Described herein are methods and compositions for the treatment of conditions, diseases, or disorders associated with autotaxin activity. The methods and compositions disclosed herein include the use of at least one autotaxin inhibitor compound.

ARYL, HETEROARY, AND HETEROCYCLIC PHARMACEUTICAL COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Complement Factor D inhibitors, pharmaceutical compositions, and uses thereof, as well as processes for their manufacture are provided. The compounds provided include Formula I, Formula II, Formula III, Formula IV, and Formula V, or a pharmaceutically acceptable salt, prodrug, isotopic analog, N-oxide, or isolated isomer thereof, optionally in a pharmaceutically acceptable composition. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade.

Discovery, optimization, and biological evaluation of 5-(2- (trifluoromethyl)phenyl)indazoles as a novel class of transient receptor potential A1 (TRPA1) antagonists

A high throughput screening campaign identified 5-(2-chlorophenyl)indazole compound 4 as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC50 = 1.23 μM. Hit to lead medicinal chemistry optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the phenyl ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound 31, a potent and selective antagonist of TRPA1 in vitro (IC50 = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain.

The synthesis and SAR of calcitonin gene-related peptide (CGRP) receptor antagonists derived from tyrosine surrogates. Part 2

Various substituted indazole and benzoxazolone amino acids were investigated as d-tyrosine surrogates in highly potent CGRP receptor antagonists. Compound 3, derived from the 7-methylindazole core, afforded a 30-fold increase in CGRP binding potency compared with its unsubstituted indazole analog 1. When dosed at 0.03 mg/kg SC, compound 2 (a racemic mixture of 3 and its (S)-enantiomer) demonstrated robust inhibition of CGRP-induced increases in mamoset facial blood flow up to 105 min. The compound possesses a favorable predictive in vitro toxicology profile, and good aqueous solubility. When dosed as a nasal spray in rabbits, 3 was rapidly absorbed and showed good intranasal bioavailability (42%).

Selection of an enantioselective process for the preparation of a CGRP receptor inhibitor

(R)-N-(3-(7-Methyl-1H-indazol-5-yl)-1-(4-(1-methylpiperidin-4-yl) piperazine-1-yl)-1-oxopropan-2-yl)-4-(2-oxo-1,2-dihydroquinolin-3-yl) piperidine-1-carboxamide (1) is a potent calcitonin gene-related peptide (CGRP) receptor antagonist. We have developed a convergent, stereoselective, and economical synthesis of the hydrochloride salt of 1 and demonstrated the synthesis on a multikilogram scale. Two different routes to the chiral indazolyl amino ester subunit were developed utilizing either a Rh-catalyzed asymmetric hydrogenation or a biocatalytic process to install the single chiral center. The advantages and disadvantages of each of these process routes are discussed, as are challenges addressed in the assembly of the final drug substance.

CGRP ANTAGONISTS

The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R1, R2 and R3 are defined as stated hereinafter, the tautomers, the isomers, the diastereomers, the enantiomers, the hydrates, the mixtures thereof and the salts thereof and the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

Efficient and scalable synthesis of 3,5,7-trisubstituted 1H-indazoles as potent IKK2 inhibitors

Efficient and scalable chemical approaches to 3,5,7-trisubstituted 1H-indazoles were developed and applied to the synthesis of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indazol-3-yl]-1-piperidinecarboxylate, a key intermediate for 3,5,7-trisubstit

HETEROCYCLIC ANTI-MIGRAINE AGENTS

The present invention relates to compounds of Formula (I) as antagonists of calcitonin gene-related peptide receptors (“CGRP-receptor”), pharmaceutical compositions comprising them, methods for identifying them, methods of treatment using them and their use in therapy for treatment of neurogenic vasodilation, neurogenic inflammation, migraine and other headaches, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.