125872-95-9

Usage

Uses

Used in Scientific Research:
6-Bromo-1-methyl-1H-indole 97 is used as a precursor or intermediate in the synthesis of various complex organic compounds, contributing to the advancement of chemical research and development.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Bromo-1-methyl-1H-indole 97 is used as a building block for the production of pharmaceuticals, playing a crucial role in the development of new drugs and therapeutic agents.
Used in Polymers and Plastics Industry:
6-Bromo-1-methyl-1H-indole 97 is employed in the synthesis of certain polymers and plastics, where it may contribute to the modification of material properties, such as stability, reactivity, or other characteristics.
Safety Precautions:
As with most chemicals, it is essential to follow safety protocols when handling 6-Bromo-1-methyl-1H-indole 97 to minimize health risks associated with improper exposure.

InChI:InChI=1/C9H8BrN/c1-11-5-4-7-2-3-8(10)6-9(7)11/h2-6H,1H3

Upstream product

• 52415-29-9 6-bromo-1H-indole 
• 74-88-4 methyl iodide 
• 10075-50-0 5-bromo-1H-indole 
• 74-83-9 methyl bromide 
• 50-00-0 formaldehyd 

Downstream Products

• 20996-87-6 1-methyl-1H-indole-6-carbonitrile 
• 1204-32-6 methyl 1-methylindole-6-carboxylate 
• 884507-19-1 1‐methyl‐6‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐1H‐indole 
• 481630-24-4 6-(4-trifluoromethylphenyl)-1-methyl-1H-indole 
• 346585-03-3 (1-methyl-1H-indol-6-yl)boronic acid 
• 199590-61-9 N₆-Methoxy-N₆,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)-sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamide 
• 199590-00-6 6-(hydroxymethyl)-N-methylindole 
• 1092661-44-3 C₁₈H₁₆BrNO₃ 
• 1356053-21-8 C₂₄H₁₉BrN₂O 
• 1392408-58-0 4-(tert-butyl)phenyl 6-bromo-1-methylindole-3-carboxylate 
• 25055-65-6 6-bromo-1-methyl-1H-indole-3-carbaldehyde 

Relevant academic research and scientific papers

Electronic Nature of Ketone Directing Group as a Key to Control C-2 vs C-4 Alkenylation of Indoles

A novel mode of achieving site selectivity between C-2 and C-4 positions in the indole framework by altering the property of the ketone directing group is disclosed. Methyl ketone, as directing group, furnishes exclusively C-2 alkenylated product, whereas trifluoromethyl ketone changes the selectivity to C-4, indicating that the electronic nature of the directing group controls the unusual choice between a 5-membered and a 6-membered metallacycle. The screening of other carbonyl-derived directing groups reveals that strong and weak directing groups exhibit opposite selectivity. Experimental controls and deuteration experiments lend support to the proposed mechanism.

Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones

An isothiourea-catalyzed enantioselective annulation protocol using indolin-2-imines with a series of α,β-unsaturated p-nitrophenyl esters for the synthesis of tetrahydro-α-carbolinones was developed. Using 5 mol % of the isothiourea HyperBTM as the Lewis base catalyst, this process allows the enantioselective preparation of a range of C(4)-substituted tetrahydro-α-carbolinones in good to excellent yield and with high enantioselectivity (20 examples, 32-99% yield and up to 99:1 er).

Catalytic generation of borenium ions by cooperative B-H bond activation: The elusive direct electrophilic borylation of nitrogen heterocycles with pinacolborane

The B-H bond of typical boranes is heterolytically split by the polar Ru-S bond of a tethered ruthenium(II) thiolate complex, affording a ruthenium(II) hydride and borenium ions with a dative interaction with the sulfur atom. These stable adducts were spectroscopically characterized, and in one case, the B-H bond activation step was crystallographically verified, a snapshot of the σ-bond metathesis. The borenium ions derived from 9-borabicyclo[3.3.1] nonane dimer [(9-BBN)2], pinacolborane (pinBH), and catecholborane (catBH) allowed for electrophilic aromatic substitution of indoles. The unprecedented electrophilic borylation with the pinB cation was further elaborated for various nitrogen heterocycles.

Design, synthesis and biological evaluation of novel 2-sulfonylindoles as potential anti-inflammatory therapeutic agents for treatment of acute lung injury

Acute lung injury (ALI) is primarily driven by inflammation that severely impacts lung function. Novel 2-sulfonylindoles were recently shown to exhibit anti-inflammatory activity through the inhibition of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) production. Here, we synthesized 31 compounds which contained 2-sulfonylindole structure. The compounds 8a, 9g, 9h and 9k exhibited dose-dependent anti-inflammatory activity in vitro. Structural-activity relationship analysis revealed that the introduction of sulfonyl group in indole nucleus may be successful to obtain new anti-inflammatory structures and leads. The compounds 9h and 9k also decreased liposaccharide (LPS)-induced IL-6, IL-1β and vascular cell adhesion molecule-1 (VCAM-1) mRNA expression, both in vitro and in an in vivo model of ALI. Furthermore, the compounds 9h and 9k at a high dose (20 mg/kg) significantly protected against LPS-induced ALI in mice. These results show that compounds 9h and 9k could be a promising lead structure for the treatment of ALI.

Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position

Herein, Rh(III)-catalyzed C4-selective C?H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished. (Figure presented.).

Benzoheterocycle substituted phenanthridine quaternary ammonium salt derivative as well as preparation method and application thereof

The invention discloses a benzoheterocycle substituted phenanthridine quaternary ammonium salt derivative and a preparation method and application thereof, the benzoheterocycle substituted phenanthridine quaternary ammonium salt derivative has a structure

Silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof

The invention discloses a silicon-based rhodamine fluorescent staining reagent as well as a preparation method and application thereof, and belongs to the field of organic chemistry and biochemistry.According to the silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof of the invention, a silicon atom substituted rhodamine derivative is used asa basic frame, and is modified with aromatic amines in different forms, so that the silicon-based rhodamine fluorescent staining reagent which has large Stokes shift and high fluorescence intensity and can mark immunoglobulin IgG can be synthesized, so that the silicon-based rhodamine fluorescent staining reagent can be used for in-vitro SARS-CoV2-virus specific antibody fluorescence ELISA detection. The silicon-based rhodamine fluorescence staining reagent has large Stokes shift (greater than 140 nm), can effectively avoid mutual interference of excitation light and emitted light, and is high in detection sensitivity; a fluorescence ELISA detection method established based on the fluorescence antibody can be suitable for microplate readers with different bandwidths, and is wide in application range.

Lysosome targeted staining reagent based on carbon atom rhodamine derivative skeleton as well as preparation method and application of lysosome targeted staining reagent

The invention discloses a lysosome targeted staining reagent based on a carbon atom rhodamine derivative skeleton and a preparation method and application of the lysosome targeted staining reagent. According to the lysosome targeted staining reagent, the carbon atom substituted amino rhodamine derivative skeleton is used as the basis of lysosome dye, and through reasonable regulation and control and design of different forms of aromatic amines, the lysosome targeted staining reagent with different emission wavelengths based on the carbon atom rhodamine derivative skeleton is obtained by usingthe carbon atom rhodamine derivative skeleton as a raw material, can realize ultralow-concentration targeted imaging while realizing rapid targeted staining, has high biocompatibility, and does not interfere with the physiological activity of living cells. Besides, the staining reagent has the characteristic of ultra-large Stokes shift, so that imaging interference caused by scattered light of exciting light is basically avoided during biological imaging, and the dye also has specific performance of high signal-to-noise ratio imaging. The preparation method disclosed by the invention is high in yield and mild in reaction condition, and the prepared staining reagent is large in Stokes shift and high in targeting property.

Tandem iridium-catalyzed decarbonylative c-h activation of indole: Sacrificial electron-rich ketone-assisted bis-arylsulfenylation

Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp?IrCl2]2) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) through the formation of six- and five-membered iridacycles at the C2 and C4 positions, respectively. Mechanistic studies show that a C-H activation-induced C-C activation is involved in the catalytic cycle.

Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue

A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.