399-51-9

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoroindole is used as a reagent for the synthesis of tryptophan dioxygenase inhibitors, specifically pyridyl-ethenyl-indoles, which serve as potential anticancer immunomodulators. This application is due to its ability to modulate the immune response and potentially combat cancer cells.
Used in Antimicrobial Applications:
6-Fluoroindole is employed as an antifungal and antibacterial agent, leveraging its properties to inhibit the growth of fungi and bacteria, making it useful in the development of new antimicrobial drugs.
Used in Psychiatry and Neurology:
As a potent selective serotonin reuptake inhibitor (SSRI), 6-Fluoroindole is used in the treatment of various psychiatric and neurological disorders, such as depression and anxiety, by modulating the levels of serotonin in the brain.
Used in HIV Treatment:
6-Fluoroindole serves as an inhibitor of HIV-1 attachment, which can potentially be utilized in the development of new therapeutic strategies to combat HIV infection by preventing the virus from binding to host cells.

InChI:InChI=1/C8H6FN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H

Upstream product

• 3093-97-8 6-fluoro-1H-indole-2-carboxylic acid 
• 96631-90-2 N,N-dimethyl-2-(4-fluoro-2-nitrophenyl)ethenylamine 
• 459-57-4 4-fluorobenzaldehyde 
• 446-10-6 2-nitro-4-fluorotoluene 
• 348-37-8 6-fluoro-1H-indole-2-carboxylic acid ethyl ester 
• 658-27-5 m-fluorophenylhydrazine 
• 169674-57-1 5-chloro-6-fluoro-1H-indole 
• 463976-52-5 6-fluoro-1-(p-toluenesulfonyl)indole 
• 2343-23-9 6-fluoroindoline 
• 1065183-63-2 (E)-(4-fluoro-2-nitrophenyl)ethanal semicarbazone 
• 120192-70-3 1-Dimethylamino-2-(4-fluoro-2-nitro)phenylethene 
• 255724-71-1 5-fluoro-2-iodoaniline 
• 136818-43-4 methyl 6-fluoroindole-2-carboxylate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 2795-41-7 6-fluoro-1H-indole-3-carbaldehyde 
• 480435-81-2 3-(6-fluoro-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
• 593267-71-1 methyl 4-((6-fluoro-1H-indol-3-yl)methyl)benzoate 
• 593267-72-2 4-(6-fluoro-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid methyl ester 
• 741265-04-3 6-fluoro-3-iodo-1H-indole 
• 913320-98-6 6-fluoro-1H-indol-3-yl-oxo-acetic acid 
• 882043-75-6 1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-fluoroindole 
• 463976-52-5 6-fluoro-1-(p-toluenesulfonyl)indole 
• 649550-98-1 2,2,2-trifluoro-1-(6-fluoro-1H-indol-3-yl)ethanone 
• 180161-14-2 6-fluoro-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole 
• 169505-89-9 [2-(6-fluoro-1H-indol-3-yl)-1,1-dimethylethyl]amine 
• 957373-17-0 C₁₈H₁₈FNO 
• 676125-69-2 4-(6-fluoro-indol-1-ylmethyl)-piperidine-1-carboxylic acid benzyl ester 
• 676125-72-7 1-(1-benzhydryl-azetidin-3-ylmethyl)-6-fluoro-1H-indole 

Relevant academic research and scientific papers

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis

A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.

A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides

A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

Room temperature dehalogenation of (hetero)aryl halides with magnesium/methanol

Magnesium in methanol was found to be an effective and inexpensive reagent for the dehalogenation of (hetero)aryl chlorides, bromides and iodides under mild conditions. The halogen/hydrogen exchange proceeded at room temperature and tolerated functional groups such as esters, nitriles, alcohols, and alkenes.

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer

Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.

Development of indole sulfonamides as cannabinoid receptor negative allosteric modulators

Existing CB1 negative allosteric modulators (NAMs) fall into a limited range of structural classes. In spite of the theoretical potential of CB1 NAMs, published in vivo studies have generally not been able to demonstrate the expected therapeutically-relevant CB1-mediated effects. Thus, a greater range of molecular tools are required to allow definitive elucidation of the effects of CB1 allosteric modulation. In this study, we show a novel series of indole sulfonamides. Compounds 5e and 6c (ABD1075) had potencies of 4 and 3?nM respectively, and showed good oral exposure and CNS penetration, making them highly versatile tools for investigating the therapeutic potential of allosteric modulation of the cannabinoid system.

PROCESS FOR THE MANUFACTURE OF IDALOPIRDINE

Disclosed herein is a process for the preparation of idalopirdine and pharmaceutically acceptable salts thereof.

Catalytic synthesis method of indole compounds

The invention discloses a catalytic synthesis method of indole compounds.The method includes the following steps of firstly, conducting stirring reaction on ortho-nitrostyrolene or derivatives of ortho-nitrostyrolene, bis(pinacolato)diboron, alkali and low-grade saturated monohydric alcohol under the atmosphere of nitrogen; secondly, cooling the reaction product in the first step to the room temperature, adding ethyl acetate to be sufficiently mixed, and washing with ethyl acetate after filtering; thirdly, spin-drying low-grade saturated monohydric alcohol in an organic phase of the material obtained in the second step, passing through a silica gel column, and drip washing the silica gel column with eluent composed of petroleum ether and ethyl acetate to obtain pure products, namely, the indole compounds.By means of the method, under the neutral conditions, bis(pinacolato)diboron low in price serves as the raw material, friendly low-grade saturated monohydric alcohol serves as the solvent, the indole compounds are obtained through simple operation, the raw materials are low in price and easy to obtain, efficiency and safety are high, and wide expandability and good industrial application prospects are achieved.

Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles

Bismuth(III) acetate is a safe, inexpensive, and selective facilitator of sequential protodeboronations, which when used in conjunction with Ir-catalyzed borylations allows access to a diversity of borylated indoles. The versatility of combining Ir-catalyzed borylations with Bi(III)-catalyzed protodeboronation is demonstrated by selectively converting 6-fluoroindole into products with Bpin groups at the 4-, 5-, 7-, 2,7-, 4,7-, 3,5-, and 2,4,7-positions and the late-stage functionalization of sumatriptan.

Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4- phenylpyridine derivatives in vitro

A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 × 103- and 2.0 × 103- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 μM), respectively.