22190-38-1

Basic information

• Product Name: 1-ACETYL-5-BROMOINDOLINE
• Synonyms: 1-(5-BROMO-2,3-DIHYDRO-1H-INDOL-1-YL)ETHAN-1-ONE;1-ACETYL-5-BROMO-2,3-DIHYDROINDOLE;1-ACETYL-5-BROMOINDOLINE;BUTTPARK 75\04-10;1-acetyl-5-bromoindoline crystalline;1-Acetyl-5-bromoindoline,97%;1-Acetyl-5-bromoindoline,98%;1-ACETYL-5-BROMOINDOLINE 98%
• CAS NO: 22190-38-1
• Molecular Formula: C₁₀H₁₀BrNO
• Molecular Weight: 240.0965
• EINECS: -0
• Product Categories: Halides;Pyrroles & Indoles;Pyrroles & Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;IndolesBuilding Blocks
• Mol File: 22190-38-1.mol

Chemical Properties

• Melting Point: 118-121°C
• Boiling Point: 423.6 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: /
• Density: 1.529 g/cm³
• Vapor Pressure: 2.2E-07mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: −20°C
• PKA: 0.27±0.20(Predicted)
• BRN: 165052
• CAS DataBase Reference: 1-ACETYL-5-BROMOINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-5-BROMOINDOLINE(22190-38-1)
• EPA Substance Registry System: 1-ACETYL-5-BROMOINDOLINE(22190-38-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-52/53
• Safety Statements: 26-36/37/39-61
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 22190-38-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-ACETYL-5-BROMOINDOLINE is used as a building block for the synthesis of various pharmaceuticals due to its ability to participate in cross-coupling reactions and other organic transformations, facilitating the creation of a wide range of drug molecules.
Used in Organic Synthesis:
1-ACETYL-5-BROMOINDOLINE is used as an intermediate in organic synthesis for the production of other organic compounds, leveraging its reactivity and structural attributes to form complex molecules.
Used in Medicinal Chemistry:
1-ACETYL-5-BROMOINDOLINE is used as a starting material for the synthesis of compounds with biological activity, indicating its potential in the development of new therapeutic agents and contributing to advancements in medicinal chemistry.

InChI:InChI=1/C10H10BrNO/c1-7(13)12-5-4-8-6-9(11)2-3-10(8)12/h2-3,6H,4-5H2,1H3

Upstream product

• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 120-72-9 indole 
• 22190-33-6 5-bromoindoline 
• 75-36-5 acetyl chloride 
• 496-15-1 1-indoline 

Downstream Products

• 10075-50-0 5-bromo-1H-indole 
• 1272181-71-1 1-acetyl-5-bromoindoline-6-sulfonamide 
• 22190-33-6 5-bromoindoline 
• 64-17-5 ethanol 
• 937591-32-7 1-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-indol-1-yl]ethanone 
• 1593884-62-8 1-acetyl-5-(4-methylpyridin-3-yl)-2,3-dihydro-1H-indole 
• 1593884-60-6 1-acetyl-5-(5-phenylpyridin-3-yl)-2,3-dihydro-1H-indole 
• 1593884-58-2 1-[5-(1-acetyl-2,3-dihydro-1H-indol-5-yl)pyridin-3-yl]ethanol 
• 1593884-55-9 1-acetyl-5-(5-methoxypyridin-3-yl)-2,3-dihydro-1H-indole 
• 1514197-61-5 1-[5-(1-acetyl-2,3-dihydro-1H-indol-5-yl)pyridin-3-yl]ethanone 
• 1593882-46-2 1-acetyl-5-(5-fluoropyridin-3-yl)-2,3-dihydro-1H-indole 
• 1593884-53-7 5-(1-acetyl-2,3-dihydro-1H-indol-5-yl)pyridine-3-carbonitrile 
• 1603838-10-3 ethyl 3-(1-acetyl-5-bromoindolin-7-yl)propanoate 
• 1612872-73-7 N-(1-acetyl-5-bromoindolin-7-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Predictable site-selective functionalization: Promoter group assistedpara-halogenation ofN-substituted(hetero)aromatics under metal-free condition

Herein, regioselectivepara-C-H halogenation ofN-pyrimidyl (hetero)aromatics through SEAr (electrophilic aromatic substitution) type reaction is disclosed. SEAr type reaction has been utilized for the C5-bromination of indolines (para-selective) withN-bromosuccinimide under metal and additive-free conditions in good to excellent yields. The developed methodology is also applicable for iodination and challenging chlorination. The pyrimidyl group is identified as a reactivity tuner that also controls the regioselectivity. The present method is also applicable for selective halogenation of aniline, pyridine, indole, oxindole, pyrazole, tetrahydroquinoline, isoquinoline, and carbazole. DFT studies such as Fukui nucleophilicity and natural charge maps also support the observedp-selectivity. Post-functionalization of the title compound into the corresponding arylated, olefinated, and dihalogenated products is achieved in a one-pot, two-step fashion. Late-stage C-H bromination was also executed on drug/natural molecules (harmine, etoricoxib, clonidine, and chlorzoxazone) to demonstrate the applicability of the developed protocol.

Indoline‐6‐sulfonamide inhibitors of the bacterial enzyme dape

Inhibitors of the bacterial enzyme dapE‐encoded N‐succinyl‐L,L‐diaminopimelic acid desuccinylase (DapE; EC 3.5.1.18) hold promise as antibiotics with a new mechanism of action. Herein we describe the discovery of a new series of indoline sulfonamide DapE inhibitors from a high‐throughput screen and the synthesis of a series of analogs. Inhibitory potency was measured by a ninhydrin‐based DapE assay recently developed by our group. Molecular docking experiments suggest active site binding with the sulfonamide acting as a zinc‐binding group (ZBG).

The Relation Between Position and Chemical Composition of Bis-Indole Substituents Determines Their Interactions with G-Quadruplex DNA

G-quadruplex (G4) DNA structures are linked to fundamental biological processes and human diseases, which has triggered the development of compounds that affect these DNA structures. However, more knowledge is needed about how small molecules interact with G4 DNA structures. This study describes the development of a new class of bis-indoles (3,3-diindolyl-methyl derivatives) and detailed studies of how they interact with G4 DNA using orthogonal assays, biophysical techniques, and computational studies. This revealed compounds that strongly bind and stabilize G4 DNA structures, and detailed binding interactions which for example, show that charge variance can play a key role in G4 DNA binding. Furthermore, the structure–activity relationships generated opened the possibilities to replace or introduce new substituents on the core structure, which is of key importance to optimize compound properties or introduce probes to further expand the possibilities of these compounds as tailored research tools to study G4 biology.

Efficient synthesis process of medical intermediate 5-bromoindole

The invention discloses an efficient synthesis process of a medical intermediate 5-bromoindole, comprising the following steps of: using an indole compound as a raw material, carrying out low-pressureliquid-phase hydrogenation to destroy five-membered ring conjugation of indole to obtain an indoline compound; enabling the indoline compound to react with an acylation reagent, and protecting nitrogen, so as to obtain an N-acyl indoline compound; carrying out bromination on the N-acyl indoline compound to obtain a 5-bromo-N-acyl indoline compound; carrying out deacylation protection on the 5-bromo-N-acyl indoline compound to obtain a 5-bromoindoline compound; and carrying out oxidative dehydrogenation on the 5-bromoindoline compound by using oxygen or air under the action of a cuprous catalyst and nitric oxide to obtain the target compound 5-bromoindole. The steps involved in the process are convenient to operate, the conditions are mild, and environmental pollution is reduced; finally,the prepared product is high in yield, high in purity and low in energy consumption.

Cooperativity within the catalyst: alkoxyamide as a catalyst for bromocyclization and bromination of (hetero)aromatics

Alkoxyamide has been reported as a catalyst for the activation ofN-bromosuccinimide to perform bromocyclization and bromination of a wide range of substrates in a lipophilic solvent, where adequate suppression of the background reactions was observed. The key feature of the active site is the alkoxy group attached to the sulfonamide moiety, which facilitates the acceptance as well as the delivery of bromonium species from the bromine source to the substrates.

COMPOUND HAVING ERK KINASE INHIBITORY ACTIVITY AND USE THEREOF

The invention relates to a compound of formula (I): wherein variables are as defined in the specification. The compound is an inhibitor of an ERK kinase, e.g. ERK1 and/or ERK2 kinase. The invention also relates to the use of the compound and a method for preparing the compound, and a pharmaceutical composition containing the compound.

Identifying new lead structures to enhance tolerance towards drought stress via high-throughput screening giving crops a quantum of solace

Novel synthetic lead structures interacting with RCAR/(PYR/PYL) receptor proteins were identified based on the results of a high-throughput screening campaign of a large compound library followed by focused SAR studies of the three most promising hit clusters. Whilst indolinylmethyl sulfonamides 8y,z and phenylsulfonyl ethylenediamines 9y,z showed strong affinities for RCAR/ (PYR/PYL) receptor proteins in wheat, thiotriazolyl acetamides 7f,s exhibited promising efficacy against drought stress in vivo (wheat, corn and canola) combined with confirmed target interaction in wheat and arabidopsis thaliana. Remarkably, binding affinities of several representatives of 8 and 9 were on the same level or even better than the essential plant hormone abscisic acid (ABA).

N-{[2-(PIPERIDIN-1-YL)PHENYL](PHENYL)METHYL}-2-(3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXA ZIN-7-YL)ACETAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ROR-GAMMA MODULATORS FOR TREATING AUTOIMMUNE DISEASES

The present invention provides e.g. N-{[2-(piperidin-1-yl)phenyl] (phenyl)methyl}-2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)acetamide derivatives and related compounds as ROR-gamma modulators for treating e.g. autoimmune diseases, autoimmune-related diseases, inflammatory diseases, metabolic diseases, fibrotic diseases or cholestatic diseases, such as e.g. arthitis and asthma.

Environment-friendly synthesis method for medicine intermediate 5-bromoindole

The invention relates to an environment-friendly synthesis method for a medicine intermediate 5-bromoindole. The method comprises the following steps: (1) subjecting indole to low-temperature low-pressure liquid-phase hydrogenation in the presence of a metal catalyst, so as to obtain indoline; (2) subjecting indoline to an action with an acetylation reagent, so as to produce N-acetylindoline; (3) subjecting N-acetylindoline to a clean bromination reaction, so as to produce N-acetyl-5-bromoindoline; (4) subjecting N-acetyl-5-bromoindoline to deacetylation under acidic conditions, so as to obtain 5-bromoindoline; and (5) subjecting 5-bromoindoline to oxidative dehydrogenation, thereby preparing the key medicine intermediate 5-bromoindole. Compared with the prior art, the method has the beneficial effects that a new environment-friendly synthesis process is developed, compared with the original process, bromo isomers of the 5-bromoindole product are effectively controlled, and the safety of medicine products can be higher; compared with the original acetic anhydride and bromine bromination process, the reaction conditions are mild, the environmental pollution is light, and the cost is low; and the equipment investment is small, the process is simple, the operation is easy, the equipment corrosion is low, and the process is more applicable to industrial production.

Preparation method of drug intermediate 5-bromoindole

The invention relates to a preparation method of a drug intermediate 5-bromoindole. The preparation method uses an N-acyl indoline compound 3 as a raw material, a 5-bro-N-acyl indoline compound 4 is obtained through bromization, then a 5-bromoindole compound 5 is obtained through diacylation protection, and a target compound 6, namely 5-bromoindole, is obtained through oxidative dehydrogenation. The preparation method is suitable for large-scale production, the production cost is relatively lower, colors can be thoroughly removed through pure recrystallization, and the preparation method has the positive significance on application of the 5-bromoindole and quality control of relevant drugs.