59541-83-2

Usage

Uses

Used in Pharmaceutical Industry:
1H-INDOLE, 5-FLUORO-2-PHENYLis used as a key intermediate in the synthesis of pharmaceutical drugs. Its unique structure allows for the development of new drugs with specific therapeutic properties, targeting various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical field, 1H-INDOLE, 5-FLUORO-2-PHENYLis utilized as a precursor for the creation of agrochemicals. These compounds can be used in the development of pesticides, herbicides, and other agricultural products to improve crop yield and protect plants from pests and diseases.
Used in Organic Synthesis:
1H-INDOLE, 5-FLUORO-2-PHENYLis used as a building block in organic synthesis. Its versatile structure allows for the creation of a wide range of organic compounds, which can be applied in various industries, including pharmaceuticals, materials science, and chemical research.
Used in Research and Development:
Due to its potential biological and pharmacological activity, 1H-INDOLE, 5-FLUORO-2-PHENYLis used in research and development for exploring new drug candidates and understanding their mechanisms of action. This helps in advancing the knowledge of medicinal chemistry and contributes to the discovery of innovative treatments and therapies.

Upstream product

• 93-89-0 benzoic acid ethyl ester 
• 109463-68-5 N-trimethylsilyl-4-fluoro-o-toluidine 
• 399-19-9 1-(4-fluorophenyl)-2-(1-phenylethylidene)hydrazine 
• 401-25-2 N-(4-fluoro-2-methylphenyl)benzamide 
• 536-74-3 phenylacetylene 
• 98-88-4 benzoyl chloride 
• 98-81-7 1-bromovinylbenzene 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 1054566-78-7 1-azido-4-fluoro-2-((E)-styryl)benzene 
• 1233533-85-1 N-(4-fluoro-2-(phenylethynyl)phenyl)-2,2,2-trifluoroacetamide 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 1253935-26-0 C₁₄H₁₂FN₃O 
• 1181455-08-2 C₁₄H₁₂FN₃ 
• 14210-81-2 1-(4-fluorophenyl)-1H-1,2,3,4-tetrazole 

Downstream Products

• 85936-39-6 5-Fluoro-3-nitro-2-phenyl-1H-indole 
• 84197-43-3 5-Fluoro-2-phenyl-indol-3-one oxime 
• 1082551-37-8 5-fluoro-2-phenyl-1H-indole-3-carbonitrile 
• 170301-01-6 6-fluoro-2-phenyl-4H-benzo<2,3-d>-1,3-oxazin-4-one 
• 1476035-13-8 1-(5-fluoro-2-phenyl-1H-indol-3-yl)-2-phenylethane-1,2-dione 
• 1613132-73-2 C₁₆H₁₁ClFNO 
• 1448544-23-7 (-)-(S)-5-fluoro-2-phenylindoline 
• 84197-46-6 N-(2-cyano-4-fluorophenyl)benzamide 
• 1385821-09-9 10-fluoro-6-phenylindolo[1,2-c]quinazoline 

Relevant academic research and scientific papers

One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones

A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).

Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones

A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.

Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis

Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.

An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives

We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is

Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics

Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.

Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones

A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.

Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones

A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.

Application of Fluorine- And Nitrogen-Walk Approaches: Defining the Structural and Functional Diversity of 2-Phenylindole Class of Cannabinoid 1 Receptor Positive Allosteric Modulators

Cannabinoid 1 receptor (CB1R) allosteric ligands hold a far-reaching therapeutic promise. We report the application of fluoro- and nitrogen-walk approaches to enhance the drug-like properties of GAT211, a prototype CB1R allosteric agonist-positive allosteric modulator (ago-PAM). Several analogs exhibited improved functional potency (cAMP, β-arrestin 2), metabolic stability, and aqueous solubility. Two key analogs, GAT591 (6r) and GAT593 (6s), exhibited augmented allosteric-agonist and PAM activities in neuronal cultures, improved metabolic stability, and enhanced orthosteric agonist binding (CP55,940). Both analogs also exhibited good analgesic potency in the CFA inflammatory-pain model with longer duration of action over GAT211 while being devoid of adverse cannabimimetic effects. Another analog, GAT592 (9j), exhibited moderate ago-PAM potency and improved aqueous solubility with therapeutic reduction of intraocular pressure in murine glaucoma models. The SAR findings and the enhanced allosteric activity in this class of allosteric modulators were accounted for in our recently developed computational model for CB1R allosteric activation and positive allosteric modulation.

Iron-catalyzed reductive coupling of nitroarenes with olefins: Intermediate of iron-nitroso complex

Using a single half-sandwich iron(II) compound, CpFe(1,2-Ph2PC6H4S)(NCMe) (Cp- = C5Me5-, 1) as a catalyst, reductive coupling of nitroarenes with olefins has been achieved by a well-defined iron(II)/(EtO)3SiH system. Through either inter- or intramolecular reductive coupling, various branched amines and indole derivatives have been directly synthesized in one-pot. Mechanistic studies showed that the catalysis is initiated by activation of nitroarenes by the iron(II) catalyst with silane, generating iron-nitrosoarene intermediate for the C-N bond coupling.

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.