22190-33-6

Basic information

• Product Name: 5-BROMOINDOLINE
• Synonyms: 5-BROMOINDOLINE;AKOS BC-0891;5-BROMO-2,3-DIHYDRO-1H-INDOLE;5-Bromoindoline,98+%;5-Bromoindoline,97%;5-bromodihydroindole;1H-Indole, 5-broMo-2,3-dihydro-;5-BroMo-2,3-dihydroindole
• CAS NO: 22190-33-6
• Molecular Formula: C₈H₈BrN
• Molecular Weight: 198.06
• EINECS: -0
• Product Categories: Indoles and derivatives;Indoline & Oxindole;Halogenated Heterocycles;Heterocyclic Building Blocks;Indolines;IndolinesBuilding Blocks;Heterocycle-Indole series
• Mol File: 22190-33-6.mol

Chemical Properties

• Melting Point: 36-40 °C(lit.)
• Boiling Point: 114-115°C 5mm
• Flash Point: >230 °F
• Appearance: White to brown low melting solid
• Density: 1.514 g/cm³
• Vapor Pressure: 0.00334mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: ?20°C
• Solubility: DMSO, Methanol
• PKA: 4.35±0.20(Predicted)
• BRN: 121590
• CAS DataBase Reference: 5-BROMOINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOINDOLINE(22190-33-6)
• EPA Substance Registry System: 5-BROMOINDOLINE(22190-33-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 22190-33-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromoindoline is used as a key intermediate for the synthesis of biologically active compounds, specifically selective human β3 adrenergic receptor agonists. These agonists have potential applications in the treatment of various medical conditions, such as obesity and related metabolic disorders, by modulating the activity of the β3 adrenergic receptor.

InChI:InChI=1/C8H8BrN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-2,5,10H,3-4H2

Upstream product

• 22190-38-1 5-bromo-N-acetylindoline 

Downstream Products

• 10075-50-0 5-bromo-1H-indole 
• 22190-38-1 5-bromo-N-acetylindoline 
• 668261-20-9 methyl 3-bromo-5-[(5-bromo-2,3-dihydro-1H-indol-1-yl)sulfonyl]benzoate 
• 645417-01-2 ethyl {4-[(5-bromo-2,3-dihydro-1H-indol-1-yl)sulfonyl]-2-methylphenoxy}acetate 
• 401565-86-4 tert-butyl 4-(5-bromoindolin-1-yl)piperidine-1-carboxylate 
• 446054-18-8 5-bromo-1-(methylsulfonyl)indoline 
• 1352662-16-8 5-bromo-1-(1-phenylethyl)indoline 
• 1382484-53-8 4-[4-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl]-N-[5-(2-methyl-1,3-thiazol-4-yl)pyridin-2-yl]tetrahydro-2H-pyran-4-carboxamide 
• 1416980-05-6 (E)-tert-Butyl 5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-en-1-yl)indoline-1-carboxylate 
• 1442463-71-9 C₂₃H₁₉Br₂NO 

Relevant articles and documents

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.

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.

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Catalytic hydrogenation of functionalized amides under basic and neutral conditions

A new, base-free high turnover number (TON) catalyst for hydrogenation of simple and functionalized amides is prepared by reacting [Ru(η3-C3H5)(Ph2P(CH2)2NH2)2]BF4 and BH4- under hydrogen. The hydrogenation proceeds with C-N cleavage to form the corresponding amine and alcohol. The base-free and base-promoted hydrogenations tolerate alcohols, amines, aromatic bromides, chlorides and fluorides, ethers, certain olefins, and N-heterocyclic rings. The reaction was used to deprotect the amine groups in certain acetyl amides to form, for example, an N-heterocyclic amine containing an aryl bromide. The base-free system also selectively hydrogenates N-acyloxazolidinones without epimerization at the α-position, and reduced β-lactams to form the corresponding amino alcohols.

MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS

The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Light-sensitive protecting groups for amines and alcohols: The photosolvolysis of n-substituted 7-nitroindolines

Representative examples of primary and secondary amines were protected as urea derivatives 4 of 5-bromo-7-nitroindoline and even more efficiently as ureas 8 derived from 5,7-dinitroindoline, via high-yield reactions with carbamoyl chlorides 3 and 7, respectively. Deprotection of 4 or 8 was achieved in high yields by UV irradiation at room temperature in Pyrex vessels under neutral conditions and exclusion of air. In a similar manner the dinitroindolines serve as protecting groups for alcohols and phenols; the derived carbamates 5 and 9 can likewise be deprotected photochemically in high yields. Georg Thieme Verlag Stuttgart.

Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives

In the course of structure-activity relationship studies, diversely substituted 1-(β-D-glucopyranosyl)-isoindigo derivatives were prepared from commercially available indolines. Their antiproliferative activities were evaluated toward a panel of human solid cancer cell lines (PC 3, DLD-1, MCF-7, M4Beu, A549, PA 1), a murine cell line (L929) and a human fibroblast primary culture to get an insight into the substitution pattern required for the best biological potencies.

Synthesis of glycosyl-isoindigo derivatives

The synthesis of 1-(β-D-glucopyranosyl)-isoindigo from commercially available indoline is described. The synthetic pathway used allowed the substitution of the aromatic moiety by either electron donor or acceptor substituents.