91844-20-1

Usage

Uses

Used in Chemical Synthesis:
5-bromo-1-methyl-1H-indole-2-carboxylic acid is used as a reactant in copper-catalyzed cross-coupling reactions of indoles with H-phosphinate. This application is significant for the synthesis of complex organic molecules, particularly those containing the indole moiety, which is a common structural element in many biologically active compounds.
Used in Pharmaceutical Development:
As a building block, 5-bromo-1-methyl-1H-indole-2-carboxylic acid is utilized in the development of new pharmaceuticals. The indole ring system is a key component in many drugs, and the presence of the bromine and methyl substituents on 5-bromo-1-methyl-1H-indole-2-carboxylic acid can influence the pharmacological properties of the resulting molecules, potentially leading to the discovery of new therapeutic agents.
Used in Agrochemical Research:
5-bromo-1-methyl-1H-indole-2-carboxylic acid may also be employed in the research and development of agrochemicals. The indole structure is found in various natural products with pesticidal properties, and the modification of this core structure through the introduction of bromine and methyl groups could lead to the creation of novel agrochemicals with improved efficacy and selectivity.

Upstream product

• 16732-70-0 ethyl 5-bromoindolecarboxylate 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 

Downstream Products

• 1399296-00-4 C₁₂H₁₁BrINO₂ 
• 90766-47-5 5-bromo-1-methyl-1H-indole-2-carboxylic acid 
• 1607826-66-3 ethyl 3-[benzyl(methyl)amino]-5-bromo-1-methyl-1H-indole-2-carboxylate 
• 1607826-75-4 ethyl 5-bromo-1-methyl-3-[2-(tritylsulfanyl)ethyl]amino-1H-indole-2-carboxylate 
• 1607826-79-8 ethyl 5-bromo-3-[2-(4-chlorophenyl)ethyl]amino-1-methyl-1H-indole-2-carboxylate 
• 1607826-80-1 ethyl 5-bromo-3-[(4-iodobenzyl)amino]-1-methyl-1H-indole-2-carboxylate 
• 1607826-82-3 ethyl 5-bromo-1-methyl-3-[(4-methylphenyl)amino]-1H-indole-2-carboxylate 
• 1607826-83-4 ethyl 5-bromo-3-[(4-bromophenyl)amino]-1-methyl-1H-indole-2-carboxylate 
• 1607826-84-5 ethyl 5-bromo-3-[(4-methoxyphenyl)amino]-1-methyl-1H-indole-2-carboxylate 
• 1607826-85-6 ethyl 5-bromo-3-[4-(methoxycarbonyl)phenyl]amino-1-methyl-1H-indole-2-carboxylate 
• 1607826-86-7 ethyl 5-bromo-1-methyl-3-[(4-nitrophenyl)amino]-1H-indole-2-carboxylate 
• 1607826-87-8 ethyl 5-bromo-1-methyl-3-[(4-sulfamoylphenyl)amino]-1H-indole-2-carboxylate 
• 1607826-88-9 ethyl 5-bromo-1-methyl-3-[2-(1-methylethyl)phenyl]amino-1H-indole-2-carboxylate 
• 1607826-89-0 ethyl 5-bromo-1-methyl-3-[(2,4,6-trimethylphenyl)amino]-1H-indole-2-carboxylate 

Relevant academic research and scientific papers

Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

Tandem Rh(II) and Chiral Squaramide Relay Catalysis: Enantioselective Synthesis of Dihydro-β-carbolines via Insertion to C-H Bond and Aza-Michael Reaction

An efficient tandem rhodium(II)/squaramide relay catalysis of readily accessible indole derivatives and N-sulfonyl-1,2,3-triazoles has been developed for the enantioselective synthesis of dihydro-β-carbolines in good yield and enantioselectivity. The developed reaction involves selective insertion of in situ generated azavinyl rhodium carbene onto the C3-H bond of indole derivatives and subsequent squaramide-catalyzed enantioselective intramolecular aza-Michael reaction. Furthermore, the potential of the strategy was demonstrated through the ready conversion to potent tetrahydro-β-carbolines and the tetracyclic alkaloid core structure.

INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE (LMPTP) AND USES THEREOF

Protein tyrosine phosphatases (PTPs) are key regulators of metabolism and insulin signaling. As a negative regulator of insulin signaling, the low molecular weight protein tyrosine phosphatase (LMPTP) is a target for insulin resistance and related conditions. Described herein are compounds capable of modulating the level of activity of low molecular weight protein tyrosine phosphatase (LMPTP) and compositions, and methods of using these compounds and compositions.

Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones

A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca

INDOLINE DERIVATIVE

PROBLEM TO BE SOLVED: To provide: a compound or a pharmacologically acceptable salt thereof which inhibits a retinoic acid receptor-related orphan receptor and, due to suppression of Th-17 cell differentiation and/or suppression of IL-17 production, is effective for treatment and/or prevention of psoriasis, multiple sclerosis, rheumatic arthritis, inflammatory bowel disease, Sjogren's syndrome, systemic lupus erythematosus, chronic obstructive pulmonary disease, asthma, or colon cancer; and a pharmaceutical composition containing the compound. SOLUTION: Provided are a compound represented by the following formula or a pharmacologically acceptable salt thereof, and a pharmaceutical composition containing the compound. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

HETEROCYCLIC COMPOUNDS AS CALCIUM SENSING RECEPTOR MODULATORS FOR THE TREATMENT OF HYPERPARATHYROIDISM, CHRONIC RENAL FAILURE AND CHRONIC KIDNEY DISEASE

The invention relates to heterocyclic compounds of Formula (I) and their pharmaceutically acceptable salts, wherein the substituents are as described herein, and their pharmaceutical compositions for use in medicine for the treatment of diseases or disorders associated with the modulation of calcium sensing receptor modulators (CaSR), like e.g. hyperparathyroidism, chronic renal failure and chronic kidney disease and their complications.

COMPOUNDS AND METHODS FOR MODULATING FXR

Compounds of formula (I): formula (I) wherein variables are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating dyslipidemia and diseases related to dyslipidemia.

2,6-SUBSTITUTED-4-MONOSUBSTITUTED AMINO-PYRIMIDINE AS PROSTAGLANDIN D2 RECEPTOR ANTAGONISTS

The present invention is directed to a compound of formula (I) wherein R1 and R2 are as defined herein, or a pharmaceutically acceptable salt, hydrate, or solvate thereof, a pharmaceutically acceptable prodrug thereof, or a pharmaceutically acceptable salt, hydrate or solvate of the prodrug, a pharmaceutical composition comprising a pharmaceutically effective amount of one or more compounds of the invention in admixture with a pharmaceutically acceptable carrier, a method of treating a patient suffering from a PGD2-mediated disorder including, but not limited to, allergic disease (such as allergic rhinitis, allergic conjunctivitis, atopic dermatitis, bronchial asthma and food allergy), systemic mastocytosis, disorders accompanied by systemic mast cell activation, anaphylaxis shock, bronchoconstriction, bronchitis, urticaria, eczema, diseases accompanied by itch (such as atopic dermatitis and urticaria), diseases (such as cataract, retinal detachment, inflammation, infection and sleeping disorders) which are generated secondarily as a result of behavior accompanied by itch (such as scratching and beating), inflammation, chronic obstructive pulmonary diseases, ischemic reperfusion injury, cerebrovascular accident, chronic rheumatoid arthritis, pleurisy, ulcerative colitis and the like by administering to said patient a pharmaceutically effective amount of a compound of the invention.

Aromatic amidine derivatives useful as selective thrombin inhibitors

The present invention relates to a novel thrombin inhibitor which is effective even when orally administered. More specifically, the present invention relates to an aromatic amidine derivative represented by formula (I) and the salts thereof, which show potent selective inhibitory activity for thrombin in which (a), R, R1, R2, R3, A, W, Y and n are defined as described in the specification.