57330-37-7

Basic information

• Product Name: Methanone, (4-chlorophenyl)[2-methyl-6-(trifluoromethoxy)-1H-indol-3-yl]-
• CAS NO: 57330-37-7
• Molecular Formula: C17H11ClF3NO2
• Molecular Weight: 353.728
• Mol File: 57330-37-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Methanone, (4-chlorophenyl)[2-methyl-6-(trifluoromethoxy)-1H-indol-3-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (4-chlorophenyl)[2-methyl-6-(trifluoromethoxy)-1H-indol-3-yl]-(57330-37-7)
• EPA Substance Registry System: Methanone, (4-chlorophenyl)[2-methyl-6-(trifluoromethoxy)-1H-indol-3-yl]-(57330-37-7)

Safety Data

• Hazardous Substances Data: 57330-37-7(Hazardous Substances Data)

Upstream product

• 7446-70-0 aluminum (III) chloride 
• 57330-49-1 2-methyl-6-(trifluoromethoxy)-1H-indole 
• 12125-02-9 ammonium chloride 
• 122-01-0 4-chloro-benzoyl chloride 
• 637042-30-9 2-[[2-methyl-6-(trifluoromethoxy)-1H-indol-3-yl]thio]benzoic acid 

Downstream Products

• 1139688-48-4 methyl (2R)-2-(3-{[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl}phenoxy)butanoate 
• 668455-54-7 C₃₁H₂₉ClF₃NO₅ 
• 637042-53-6 C₂₈H₂₅ClF₃N₃O₃S 
• 57329-72-3 [3-(4-chloro-benzoyl)-2-methyl-6-trifluoromethoxy-indol-1-yl]-acetic acid 
• 1139688-44-0 3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]anisole 
• 1171817-40-5 ethyl 2-{3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenoxy}-2-methylbutanoate 
• 1171817-39-2 ethyl 2-{3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenoxy}-2-methylbutanoate 
• 668455-60-5 ethyl (2R)-2-{3-[[3-(4-chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenoxy}butyrate 
• 57330-25-3 [3-(4-chloro-benzoyl)-2-methyl-6-trifluoromethoxy-indol-1-yl]-acetic acid methyl ester 

Relevant articles and documents

Practical, highly convergent, asymmetric synthesis of a selective PPARγ modulator

A practical, highly convergent, asymmetric synthesis of a selective PPARγ modulator 1 is described. The inhibitor contains two key components, a 6-trifluoromethoxy-3-acylindole (6) and (R)-raryloxybutanoic acid derivative (10). Twomethods were developed to overcome the regioselectivity issues encountered in the preparation of the 6-substituted indole. The first involved an intramolecular Heck reaction of an iodoaryl enamine. The second involved application of a catalytic Meerwein arylation reaction between 2-nitro-4-trifluoromethoxyaniline and isopropenyl acetate and subsequent reductive cyclization. The α-aryloxybutanoic acid was prepared via an asymmetric hydrogenation of the corresponding α-aryloxy-α,β- unsaturated acid. Tetrabutylammonium iodidecatalyzed coupling of the two fragments and ester hydrolysis completed the convergent synthesis. The described convergent synthesis was used to prepare >3 kg of drug substance 1 in 50% overall yield and with >99.5% ee.

NOVEL CRYSTALLINE FORMS OF ANTIDIABETIC COMPOUNDS

Novel crystalline forms of two indole compounds connected to phenoxyalkylcarboxylic acid groups are selective PPAR gamma partial agonists that are useful in the treatment of type 2 diabetes, hyperglycemia, obesity, dyslipidemia, and the metabolic syndrome. The novel crystal forms include a crystalline free acid dihydrate and crystalline free acid anhydrate of one compound and several crystalline forms of the free acid and the sodium salt of the second compound. The invention also relates to pharmaceutical compositions comprising these novel crystal forms, processes to prepare the crystal forms and their pharmaceutical compositions, and uses of the crystal forms in the treatment of type 2 diabetes and other PPAR gamma modulated diseases.

INDOLES HAVING ANTI-DIABETIC ACTIVITY

Indoles having aryloxyalkanoic acid substituents or arylalkanoic acid substituents are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.