475039-81-7

Basic information

• Product Name: 4-Bromo-3-methyl-indole
• Synonyms: 4-Bromo-3-methyl-indole;4-bromo-3-methyl-1H-indole;1H-INDOLE,4-BROMO-3-METHYL-
• CAS NO: 475039-81-7
• Molecular Formula: C₉H₈BrN
• Molecular Weight: 210.07052
• Mol File: 475039-81-7.mol

Chemical Properties

• Melting Point: ca. 25-30℃
• Boiling Point: 325.09°C at 760 mmHg
• Flash Point: 150.409°C
• Appearance: /
• Density: 1.564g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 16.37±0.30(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 4-Bromo-3-methyl-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-3-methyl-indole(475039-81-7)
• EPA Substance Registry System: 4-Bromo-3-methyl-indole(475039-81-7)

Safety Data

• Hazardous Substances Data: 475039-81-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-3-methyl-indole is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable intermediate in the development of potential drug candidates.
Used in Organic Synthesis:
4-Bromo-3-methyl-indole is employed as a key intermediate in various organic reactions, including the synthesis of complex organic molecules and the modification of existing compounds to enhance their properties or introduce new functionalities.
Used in Drug Development:
In the pharmaceutical industry, 4-Bromo-3-methyl-indole is utilized for the development of new drug candidates. Its unique chemical properties and reactivity allow for the creation of novel compounds with potential therapeutic applications.

InChI:InChI=1/C9H8BrN/c1-6-5-11-8-4-2-3-7(10)9(6)8/h2-5,11H,1H3

Upstream product

• 52488-36-5 4-bromo-1H-indole 
• 67-56-1 methanol 
• 475039-72-6 N-allyl-N-(2-bromoallyl)-2-fluoroaniline 
• 1978-38-7 2-fluoro-N-methylaniline 
• 348-54-9 2-Fluoroaniline 
• 117531-36-9 N-allyl-2-fluoroaniline 
• 98600-34-1 4-bromo-1H-indole-3-carbaldehyde 

Downstream Products

• 1001394-89-3 4-bromo-3-methyl-1-(phenylsulfonyl)-1H-indole 
• 1384543-18-3 3-methyl-4-{4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl}-1-(4-methoxybenzyl)-1H-indole 
• 1384543-16-1 4-bromo-1-(4-methoxybenzyl)-3-methyl-1H-indole 
• 1421251-76-4 (R)-2-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)acetamide 
• 1421254-18-3 (R)-2-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)acetamide 
• 1421254-17-2 (R)-tert-butyl 4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazine-1-carboxylate 
• 1421251-18-4 6-(5-isopropyl-2-methylphenyl)-4-methyl-2-(3-methyl-1H-indol-4-yl)-5,6,7,8-tetrahydro-1,6-naphthyridine 
• 1421253-90-8 6-(5-isopropyl-2-methylphenyl)-4-methyl-2-(3-methyl-1-tosyl-1H-indol-4-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one 
• 1421253-89-5 methyl 4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)-2-vinylnicotinate 
• 1421253-88-4 methyl 2-chloro-4-methyl-6-(3-methyl-1-tosyl-1H-indol-4-yl)nicotinate 
• 1421253-83-9 6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol 
• 1421253-81-7 (R)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine 
• 1421253-80-6 (R)-6-benzyl-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine 
• 1421253-78-2 6-(4-chloro-3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-(3,3-dimethylpiperidin-1-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine 

Relevant articles and documents

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles

Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).

Discovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays

A series of potential new 5-HT2 receptor scaffolds based on a simplification of the clinically studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly selective in both functional and binding assays, had good rat PK properties and that significantly reduced acute food intake in the rat.

Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system

A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides

A highly efficient N,N′-dioxide-NiII catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98 % yield with up to 91 % enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C-C cleavage of oxiranes is accomplished by using a highly efficient N,N′-dioxide-NiII catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.

Iridium-catalyzed methylation of indoles and pyrroles using methanol as feedstock

Iridium-catalyzed methylation of indoles and pyrroles using methanol as the methylating agent was achieved. This transformation takes place via a borrowing hydrogen methodology under an air atmosphere, which constitutes a direct route to 3-methyl-indoles and methyl-pyrroles.

5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE

Provided are 5-HT2C receptor agonists. Also provided are methods for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea. Also provided are compositions comprising a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent, and methods for reducing the frequency of smoking tobacco in an individual attempting to reduce frequency of smoking tobacco; aiding in the cessation or lessening of use of a tobacco product in an individual attempting to cease or lessen use of a tobacco product; aiding in smoking cessation and preventing associated weight gain; controlling weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; reducing weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; treating nicotine dependency, addiction and/or withdrawal in an individual attempting to treat nicotine dependency, addiction and/or withdrawal; or reducing the likelihood of relapse use of nicotine by an individual attempting to cease nicotine use comprising administering a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent.

SERINE/THREONINE PAK1 INHIBITORS

Compounds having the formula I wherein A, Z, R1a, R1b, R2, R3, R4, R5, R6, R7, R9, R10, Ra, Rb and n are as defined herein are inhibitors of PAK1. Also disclosed are compositions and methods for treating cancer and hyperproliferative disorders.

TETRAHYDROPYRIDO-PYRIDINE AND TETRAHYDROPYRIDO-PYRIMIDINE COMPOUNDS AND USE THEREOF AS C5A RECEPTOR MODULATORS

The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

INDOLES AS 5-HT6 MODULATORS

The present invention relates to novel compounds of formula (I) wherein m, n, R0, R1, R2, R3 and R4 are as described herein, to pharmaceutical compositions comprising the compounds, to processes for t

Synthesis of functionalized indole- and benzo-fused heterocyclic derivatives through anionic benzyne cyclization

The development of a new method for the regioselective synthesis of functionalized indoles and six-membered benzo-fused N-, O-, and S-heterocycles is reported. The key step involves the generation of a benzyne-tethered vinyl or aryllithium compound that undergoes a subsequent intramolecular anionic cyclization. Reaction of the organolithium intermediates with selected electrophiles allows the preparation of a wide variety of indole, tetrahydrocarbazole, dihydrofenantridine, dibenzopyran, and dibenzothiopyran derivatives. Finally, the application of this strategy to the appropriate starting materials allows the preparation of some tryptamine and serotonin analogues.