115666-21-2

Usage

Uses

Used in Organic Synthesis:
7-Bromo-1H-indole-3-carbaldehyde is utilized as a key intermediate in organic synthesis, particularly for the preparation of pharmacologically active molecules and other bioactive compounds. Its unique chemical properties allow for the creation of a wide range of chemical entities with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7-Bromo-1H-indole-3-carbaldehyde is employed as a building block in the synthesis of various pharmaceuticals. Its structural features make it a valuable component in the development of new drugs with improved therapeutic properties. 7-BROMO-1H-INDOLE-3-CARBALDEHYDE's versatility in chemical reactions enables the creation of diverse drug candidates with potential applications in treating various diseases and conditions.
Used in Medicinal Chemistry Research:
7-Bromo-1H-indole-3-carbaldehyde plays a significant role in medicinal chemistry research, where it is used to explore the structure-activity relationships of indole-based compounds. Its unique chemical properties allow researchers to investigate the effects of bromine substitution and aldehyde functionality on the biological activity of indole derivatives, leading to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used in Agrochemicals:
7-Bromo-1H-indole-3-carbaldehyde also finds applications in the agrochemical industry, where it serves as a valuable intermediate in the synthesis of various agrochemicals. Its unique chemical properties enable the development of new agrochemicals with enhanced biological activity, contributing to improved crop protection and yield.

Upstream product

• 51417-51-7 7-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 577-19-5 2-nitrophenyl bromide 
• 852391-39-0 (7-bromo-1H-indol-3-yl)-N,N-dimethylmethanamine 
• 615-36-1 2-bromoaniline 
• 101080-38-0 N-(2-bromophenyl)-2-isonitrosoacetanilide 
• 20780-74-9 7-bromoisatin 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 331646-98-1 8-bromo-1H-benzo[d][1,3]oxazine-2,4-dione 
• 86915-22-2 7-bromo-3-methyl-1H-indole 
• 40619-69-0 2-(7-bromo-1H-indole-3-yl)ethylamine 
• 210569-78-1 C₂₀H₂₁BBrN₃O₄ 
• 210569-79-2 N-[(3-bromobenzylcarbamoyl)methyl]-3-(7-bromo-3H-indol-3-yl)propionamide 
• 642073-58-3 N-Boc-3-iodo-Tyr(Bn)-Leu-7-bromo-Trp-OMe 
• 642073-57-2 N-Boc-3-iodo-Tyr(Bn)-AIa-7-bromo-Trp-OMe 
• 642073-60-7 N-Boc-3-iodo-Tyr(Me)-Leu-7-bromo-Trp-OMe 

Relevant academic research and scientific papers

Selective nickel-catalyzed dehydrogenative-decarboxylative formylation of indoles with glyoxylic acid

Herein we present a new strategy for the dehydrogenative-decarboxylative coupling of indoles with glyoxylic acid. A broad range of indoles were transformed into the corresponding 3-formylindoles in moderate to good yields and excellent functional group tolerance. Notably, no N-formylation product was detected under our conditions.

Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles

A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids

We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, Na-methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished.

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)

The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)

Synthesis of polycyclic spirooxindoles via an asymmetric catalytic one-pot stepwise Aldol/chloroetherification/aromatization procedure

A general method for the synthesis of chiral pentacyclic spirooxindoles containing a tetrahydropyrano[2,3-b]indole scaffold through a one-pot stepwise sequence from 3-(3-indolomethyl)oxindole, paraformaldehyde and NCS is reported. Furthermore, the pentacyclic spirooxindoles could be transformed to bispirooxindole and other structurally diverse spirocyclic oxindoles.

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air

An efficient iodine-catalyzed chemoselective 3-formylation of free (N–H) and N-substituted indoles was achieved by using hexamethylenetetramine (HMTA) in the presence of activated carbon under air atmosphere. This new method could provide 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this catalytic formylation of indoles procedure can be applied to gram-scale synthesis.

A 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drug (by machine translation)

The invention belongs to the technical field of pharmaceutical chemistry, in particular to a kind of 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drugs. Research display inhibit one or more prostandin receptor activity can be effective for the treatment of hypertension, at least one kind of prostagladin E2 receptor in the blood pressure regulating system RAAS in the course of play a crucial role, we by changing 1 and 8 is the angle of the two groups and the distance to EP3 receptor research, we developed a new high-efficiency of the synthetic route to study a series of derivatives, all of the target compound are all new product, all of the compound through the nuclear magnetic resonance and quality of the identification of the structure. The target compound in the antibacterial, anti-tumor, analgesic, anti-platelet aggregation, the promotion of kidney part of the reabsorption of sodium and water, regulating neurotransmitter release, promote adipose tissue Lipolysis and has an important role of anti-arrhythmia. (by machine translation)

Cu-mediated oxidative dimerization of skatole to tryptanthrin, an indolo[2,1-b]quinazolone alkaloid

A one-pot conversion of skatole to tryptanthrin, an indolo[2,1-b]quinazoline alkaloid, was achieved by Cu-mediated oxidation.