590417-55-3

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMO-1-METHYL-1H-INDOLE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications. Its unique structure allows for the creation of molecules with specific biological activities, making it valuable in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 4-BROMO-1-METHYL-1H-INDOLE is utilized as an intermediate in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can enhance their effectiveness in controlling pests and weeds, thereby contributing to increased crop yields and agricultural productivity.
Used in Dye Industry:
4-BROMO-1-METHYL-1H-INDOLE is employed as a precursor in the synthesis of dyes, particularly those used in various industrial applications. Its chemical properties enable the creation of dyes with specific color characteristics and stability, making it an essential component in the formulation of high-quality dyes for textiles, plastics, and other materials.

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

Upstream product

• 52488-36-5 4-bromo-1H-indole 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 348640-06-2 4-bromo-7-azaindole 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 865-33-8 potassium methanolate 
• 90481-72-4 4-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indole 
• 86626-40-6 4-bromo-1-methylindoline 

Downstream Products

• 866721-35-9 2-(1-methyl-1H-indol-4-yl)cyclohexan-1-one 
• 898289-06-0 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 
• 1335242-66-4 4-(2-aminophenyl)-1-methylindole 
• 1392127-50-2 (E)-methyl 4-[5-(benzoyloxy)-2-oxopent-3-en-1-yl]-5-[(tert-butyldimethylsilyl)oxy]-1,3,3-trimethyl-3,4-dihydro-1H-cyclohepta[cd]indole-6-carboxylate 
• 1228023-16-2 (Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate 
• 1228023-15-1 O-(tert-butyldiphenylsilyl)-2-methylene-4-(2,2-dimethyl-4H-1,3-dioxin-4-one-6-yl)-5-(4-bromo-1-methylindol-3-yl)-5-methyl-hexan-1-ol 
• 1228023-20-8 3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester 
• 120160-29-4 1-(1-methyl-1H-indol-4-yl)-ethanone 
• 884855-67-8 4-bromo-1-methylindoline-2,3-dione 

Relevant academic research and scientific papers

A Ten-Step Total Synthesis of Speradine C

The first total synthesis of speradine C has been achieved in only ten steps from a commercially available 4-bromoindole. Salient features of the work are the formation of four rings through three cyclizations, namely a bioinspired [3+2] annulation to form the C/D rings, an NCS-mediated oxidation to construct the E ring, and a Ru-catalyzed ketohydroxylation to assemble the F ring. This work highlights how strategic ring constructions can streamline the synthesis of polycyclic compounds.

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound

The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.

Rhodium(II)-Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)-Aurantioclavine

An efficient rhodium(II)-catalyzed [4+3] cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed. Azepino[5,4,3- cd]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good

Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile

An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).

Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles

Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide

Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).

Method for preparing indole compound through air oxidation catalyzed by N-hydroxyphthalimide

The invention discloses a method for preparing an indole compound through non-transition metal catalyzed air oxidation. According to the method, the low-cost N-hydroxyphthalimide is used as a catalystand air is used as an oxidizing agent, wherein indoline compounds are oxidized in an organic solvent, and synthesis of the indoline compounds is achieved. The method has the advantages of simple reaction operation, low reaction cost, high yield, mild conditions, no heavy metal pollution and the like.

Switchable regioselection of C-H thiolation of indoles using different TMS counterions

A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.

SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE

The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof, or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof, and methods and compositions for treating or ameliorating abnormal cell pr

Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides

An efficient strategy for N/O-(deutero)alkylation of indoles and phenols with alkoxides/alcohols as the alkylation reagents is described. The consecutive detosylation/alkylation transformations feature mild reaction conditions, high ipso-selectivity, and good functional group tolerance (>50 examples). A one-pot selective N-alkylation of unprotected indoles with alcohols and TsCl is also realized. The application of this method is demonstrated by the introduction of isotope-labeled (CD3 and 13CH3) groups using the readily accessible labeled alcohols and the synthesis of pharmaceuticals.