114744-50-2

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Bromo-1,2,3,4-tetrahydro-quinoline hydrochloride is used as a key intermediate in the production of various drugs. Its unique structure allows for the creation of a range of medicinal compounds, contributing to the development of new therapeutic agents.
Used in Organic Chemistry Research:
As a versatile chemical, 5-Bromo-1,2,3,4-tetrahydro-quinoline hydrochloride is employed as a reagent in chemical reactions, facilitating the synthesis of complex organic molecules and aiding in the advancement of organic chemistry research.
Used in Drug Development:
5-Bromo-1,2,3,4-tetrahydro-quinoline hydrochloride is utilized in the study of potential pharmacological properties, playing a crucial role in the discovery and development of innovative medications for various therapeutic areas.

InChI:InChI=1/C9H10BrN.ClH/c10-8-4-1-5-9-7(8)3-2-6-11-9;/h1,4-5,11H,2-3,6H2;1H

Upstream product

• 67-56-1 methanol 
• 15115-60-3 4-bromo-2,3-dihydroinden-1-one 
• 4964-71-0 5-bromoquinoline 
• 903557-27-7 4-bromo-1-indanone oxime 

Downstream Products

• 1622173-42-5 1-(5-(8-((4-(morpholine-4-carbonyl)phenyl)amino)imidazo[1,2-a]pyrazin-6-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone 

Relevant academic research and scientific papers

Ligand-Enabled Enantioselective Csp3 –H Activation of Tetrahydroquinolines and Saturated Aza-Heterocycles by RhI

The first rhodium(I)-catalyzed enantioselective intermolecular C (Formula presented.) –H activation of various saturated aza-heterocycles including tetrahydroquinolines, piperidines, piperazines, azetidines, pyrrolidines, and azepanes is presented. The combination of a rhodium(I) precatalyst and a chiral monodentate phosphonite ligand is shown to be a powerful catalytic system to access a variety of important enantio-enriched heterocycles from simple starting materials. Notably, the C (Formula presented.) –H activation of tetrahydroquinolines is especially challenging due to the adjacent C (Formula presented.) ?H bond. This redox-neutral methodology provides a new synthetic route to α-N-arylated heterocycles with high chemoselectivity and enantioselectivity up to 97 % ee.

Iridium-catalyzed dehydrogenative α-Functionalization of (Hetero)aryl-Fused cyclic secondary amines with indoles

Herein, by employing dehydrogenation as a substrate-activating strategy, a new iridium-catalyzed direct α-functionalization of (hetero)aryl-fused cyclic secondary amines with indoles has been demonstrated, which proceeds with merits that include high step- and atom-efficiency, readily available feedstocks, a simple catalyst system, good functional group tolerance, and operational simplicity.

Simple manganese carbonyl catalyzed hydrogenation of quinolines and imines

Manganese-catalyzed hydrogenation of unsaturated molecules has made tremendous progresses recently benefiting from non-innocent pincer or bidentate ligands for manganese. Herein, we describe the hydrogenation of quinolines and imines catalyzed by simple manganese carbonyls, Mn2(CO)10 or MnBr(CO)5, thus eliminating the prerequisite pincer-type or bidentate ligands.

Method for preparing tetrahydroquinoline compounds by catalytic hydrogenation of ruthenium catalyst

The invention relates to a method for preparing tetrahydroquinoline compounds by catalytic hydrogenation of a ruthenium catalyst, which comprises the following steps: by using p-cymene ruthenium chloride dimer as a catalyst and hydrogen as a reducing agent, mixing the p-cymene ruthenium chloride dimer, phosphine ligand and quinoline compounds, and dissolving the mixture in an organic solvent to react, and carrying out post-treatment to obtain the tetrahydroquinoline derivative. Compared with the prior art, the method has the advantages of easily available raw materials, mild conditions, simpleoperation, atom economy, simple and green synthesis process, mild reaction conditions, excellent selectivity, high yield and good reaction universality, and has a wide application value in fine chemical intermediate synthesis.

Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution

An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination

We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.

Method for selective catalytic hydrogenation of aromatic heterocyclic compounds in non-hydrogen participation manner

The invention discloses a method for selective catalytic hydrogenation of aromatic heterocyclic compounds in a non-hydrogen participation manner. The method comprises the following steps: by taking 1, 5-cyclooctadiene iridium chloride dimer as a catalyst and phenylsilane as a hydrogen source, carrying out stirring reaction under mild conditions without adding a ligand, namely catalytically hydrogenating the aromatic heterocyclic compounds to obtain hydrogenated products of the aromatic heterocyclic compounds. The method has the advantages of low cost, mild reaction conditions, high selectivity and the like, and special equipment such as a high-pressure kettle and the like and high-temperature conditions which are required when hydrogen is used are avoided.

Silver-Catalyzed Reduction of Quinolines in Water

A ligand- and base-free silver-catalyzed reduction of quinolines and electron-deficient aromatic N-heteroarenes in water has been described. Mechanistic studies revealed that the effective reducing species was Ag-H. This versatile catalytic protocol provided facile, environmentally friendly, and practical access to a variety of 1,2,3,4-tetrahydroquinoline derivatives at room temperature.

DIRECT C-H AMINATION AND AZA-ANNULATION

In some aspects, the present disclosure provides methods of aminating an aromatic compound comprising reacting an aminating agent with an aromatic compound in the presence of a rhodium catalyst. In some embodiments, the methods may comprise aminating an aromatic compound which contains multiple different functional groups. The methods described herein may also be used to create bicyclic system comprising reacting an intramolecular aminating agent with an aromatic ring to obtain a second ring containing a nitrogen atom. In another aspect, the methods described herein may also be used to create a cyclic aliphatic cyclic/poly cyclic amine system comprising a reacting an intramolecular aminating agent by insertion into a C(sp3)-H bond.

Method for conducting catalytic hydrogenation on nitrogen-containing unsaturated heterocyclic compound

The invention provides a method for conducting catalytic hydrogenation on a nitrogen-containing unsaturated heterocyclic compound, and belongs to the technical field of catalytic hydrogenation. The provided method for conducting catalytic hydrogenation on the nitrogen-containing unsaturated heterocyclic compound comprises the following step: in the presence of hydrogen and a manganese catalyst, with the nitrogen-containing unsaturated heterocyclic compound as a substrate, carrying out a hydrogenation reaction. According to the method for conducting catalytic hydrogenation on the nitrogen-containing unsaturated heterocyclic compound, he adopted manganese catalyst is an NNP-type pincer manganese catalyst, has the advantages of being cheap, easy to obtain and low in toxicity compared with noble metal catalysts, has the advantages of being wide in substrate applicability and high in target product yield compared with an existing cheap metal iron catalyst or cobalt catalyst, and is higher in electron donating ability and smaller in steric hindrance compared with a PNP-type pincer manganese catalyst, and thus shows higher reaction activity in a series of hydrogenation reactions, and thetarget product yield is up to 99%.