10075-51-1

Usage

Uses

Used in Pharmaceutical Research:
1-BENZYL-5-BROMO-1H-INDOLE is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs and medicinals. Its unique structural features allow it to be a candidate for creating novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 1-BENZYL-5-BROMO-1H-INDOLE is utilized as a building block for the creation of complex organic molecules. Its bromine substituent and benzyl moiety provide opportunities for further chemical reactions and modifications, facilitating the synthesis of a wide range of organic compounds.
It is crucial to handle 1-BENZYL-5-BROMO-1H-INDOLE with care, adhering to proper safety protocols and guidelines to minimize risks and ensure its safe and effective use in research and development processes.

InChI:InChI=1/C15H12BrN/c16-14-6-7-15-13(10-14)8-9-17(15)11-12-4-2-1-3-5-12/h1-10H,11H2

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 22190-33-6 5-bromoindoline 
• 100-51-6 benzyl alcohol 
• 18359-64-3 5-bromo-1-benzylindoline 
• 75934-32-6 (4-Bromo-phenyl)-(2,2-diethoxy-ethyl)-amine 
• 1429616-67-0 N-benzyl-4-bromo-N-(2,2-diethoxyethyl)aniline 
• 3459-92-5 DBC 

Downstream Products

• 3377-71-7 N-benzylindole 
• 481630-46-0 1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole 
• 1201825-41-3 1,1'-dibenzyl-5,5'-dibromo-1H,1'H-2,3'-biindole 
• 1284216-72-3 C₁₈H₁₇NO 

Relevant academic research and scientific papers

Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids

Boronic acid was used to accelerate a three-component reaction of indoles, thiols, and glyoxylic acids for the synthesis of α-sulfanyl-substituted indole-3-acetic acids. Boronic acid catalysis to activate the α-hydroxy group in α-hydroxycarboxylic acid in

Trifluoromethanesulfonic acid-catalyzed solvent-free bisindolylation of trifluoromethyl ketones

A trifluoromethanesulfonic acid-catalyzed solvent-free bisindolylation reaction of indoles with alkyl and aryl trifluoromethyl ketones has been developed. The trifluoromethyl-substituted bisindolylalkane derivatives were synthesized in moderate to excellent yields.

Gramine Derivatives Targeting Ca2+ Channels and Ser/Thr Phosphatases: A New Dual Strategy for the Treatment of Neurodegenerative Diseases

We describe the synthesis of gramine derivatives and their pharmacological evaluation as multipotent drugs for the treatment of Alzheimer's disease. An innovative multitarget approach is presented, targeting both voltage-gated Ca2+ channels, cl

Three-component reactions of 3-arylidene-3h-indolium salts, isocyanides and amines

A multicomponent reaction of isocyanides with aryl(indol-3-yl)methylium salts and amines has been found. A series of aryl(indol-3-yl)acetimidamides was obtained in up to 96% yields. In the case of ethyl isocyanoacetate, the reaction is followed by cyclization to form 3,5-dihydro-4H-imidazol-4-one derivatives.

Tiplaxtinin, a novel, orally efficacious inhibitor of plasminogen activator inhibitor-1: Design, synthesis, and preclinical characterization

Indole oxoacetic acid derivatives were prepared and evaluated for in vitro binding to and inactivation of human plasminogen activator inhibitor-1 (PAI-1). SAR based on biochemical, physiological, and pharmacokinetic attributes led to identification of tip

A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered: N -sulfonyl-1,2,3-triazoles and indoles

An efficient and convenient protocol for the synthesis of a novel class of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles has been disclosed. The reaction proceeds via denitrogenative aza-vinyl rhodium carbene formation to give a carbonyl ylide, which with indole results in 1,3-dipolar cycloaddition followed by sequential semipinacol rearrangement/ring expansion/oxidation to produce azepino fused diindoles. The reaction shows a broad substrate scope giving up to 81% yield. Furthermore, reversible catalytic hydrogenation and photophysical studies were carried out to demonstrate the application of these molecules.

Accelerated benzylation reaction utilizing dibenzyl carbonate as an alkylating reagent

Ionic liquids can effectively accelerate slow N-benzylation reactions utilizing dibenzyl carbonate as an alkylating reagent. By applying microwave irradiation in the presence of the same ionic liquid, additional rate enhancement was accomplished.

Catalytic Electrophilic C?H Borylation Using NHC?Boranes and Iodine Forms C2-, not C3-, Borylated Indoles

Activation of N-heterocyclic carbene boranes (NHC?BH3) by I2 enables the metal-free catalytic C?H borylation of heteroarenes with formation of H2 as the by-product in a process that uses only bench stable precursors. The borylation of indoles using NHC?BH3/I2 produces C2-borylated indoles exclusively in contrast to other catalytic electrophilic C?H borylation methods. Mechanistic studies indicate that this is due to C3 to C2 boron migration facilitated by the absence of exogenous Br?nsted bases. Thus this C?H borylation methodology proceeds under sufficiently Br?nsted acidic conditions to enable the thermodynamic C2-borylated indole isomer to be formed instead of the C3 borylated-isomer. This demonstrates that electrophilic C?H borylation can be used to access a wider range of borylated regioisomers than reported to date.

New Inhibitor Targeting Signal Transducer and Activator of Transcription 5 (STAT5) Signaling in Myeloid Leukemias

Signal transducers and activators of transcription 5 (STAT5s) are crucial effectors of tyrosine kinase oncogenes in myeloid leukemias. Inhibition of STAT5 would contribute to reducing the survival of leukemic cells and also tackling their chemoresistance. In a first screening experiment, we identified hit 13 as able to inhibit STAT5 phosphorylation and leukemic cell growth. The synthesis of 18 analogues of 13 allowed us to identify one compound, 17f, as having the most potent antileukemic effect. 17f inhibited the growth of acute and chronic myeloid leukemia cells and the phosphorylation and transcriptional activity of STAT5. Importantly, 17f had minimal effects on bone marrow stromal cells that play vital functions in the microenvironment of hematopoietic and leukemic cells. We also demonstrated that 17f inhibits STAT5 but not STAT3, AKT, or Erk1/2 phosphorylation. These results suggest that 17f might be a new lead molecule targeting STAT5 signaling in myeloid leukemias.

Enantioselective Friedel-Crafts alkylations of α,β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

An enantioselective Friedel-Crafts alkylation with α,β-unsaturated 2-acyl imidazoles and electron-rich aromatic nucleophiles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes has been accomplished. These α,β-unsaturated 2-acyl imidazol