1408282-25-6

Basic information

• Product Name: 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester
• Synonyms: 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester;Rucaparib Impurity 4;methyl 3-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-6-fluoro-1H-indole-4-carboxylate
• CAS NO: 1408282-25-6
• Molecular Formula: C₂₀H₁₅FN₂O₄
• Molecular Weight: 366.3425032
• Mol File: 1408282-25-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 579.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.434±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 15.32±0.30(Predicted)
• CAS DataBase Reference: 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester(1408282-25-6)
• EPA Substance Registry System: 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester(1408282-25-6)

Safety Data

• Hazardous Substances Data: 1408282-25-6(Hazardous Substances Data)

Usage

Description

3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester is a complex organic chemical compound characterized by a methyl ester derivative of a carboxylic acid with a fluoro-substituted indole ring. The molecule features a dihydro-1,3-dioxo-2H-isoindol-2-yl group attached to an ethyl chain, which may confer unique biological activities and physicochemical properties, particularly relevant for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester is used as a pharmaceutical agent for its potential biological activity. The presence of the fluoro-substituted indole ring and the dihydro-1,3-dioxo-2H-isoindol-2-yl group may contribute to its interaction with biological targets, making it a candidate for the development of new drugs.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, this compound serves as a research tool for studying the effects of structural modifications on biological activity. The fluoro substitution and the specific arrangement of functional groups provide a basis for exploring structure-activity relationships and optimizing drug candidates for various therapeutic applications.
Used in Drug Design and Development:
3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-6-fluoro-1H-indole-4-carboxylic acid methyl ester is utilized in drug design and development processes to create novel therapeutic agents. Its unique structural features can be leveraged to improve pharmacokinetics, selectivity, and potency, leading to the discovery of new drugs with enhanced efficacy and safety profiles.

Upstream product

• 2913-97-5 N-phthalimidyl-2-aminoacetaldehyde 
• 1082040-43-4 6-fluoro-1H-indole-4-carboxylic acid methyl ester 
• 33184-16-6 5-fluoro-2-methylbenzoic acid 
• 697739-03-0 5-fluoro-2-methyl-3-nitrobenzoic acid methyl ester 

Downstream Products

• 283173-84-2 4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde 
• 773059-19-1 8-fluoro-2-((4-methylaminomethyl)phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one hydrochloride 
• 283173-50-2 Rucaparib 
• 1408282-26-7 6-fluoro-3,10-diazatricyclo[6.4.1.0^4,13]trideca-1,4⁽¹³⁾,5,7-tetraen-9-one 

Relevant articles and documents

ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS

The disclosure relates to anti-cancer compounds derived from nuclear steroid receptor binders, to products containing the same, as well as to methods of their use and preparation.

Multkilogram scale-up of a reductive alkylation route to a novel PARP inhibitor

Novel PARP inhibitor 1 is a promising new candidate for treatment of breast and ovarian cancer. A modified synthetic route to 1 has been developed and demonstrated on 7 kg scale. In order to scale up the synthesis to multikilogram scale, several synthetic challenges needed to be overcome. The key issues included significant thermal hazards present in a Leimgruber-Batcho indole synthesis, a low-yielding side-chain installation, a nonrobust Suzuki coupling and hydrogen cyanide generation during a reductive amination. In addition to these issues, changing from intravenous to oral delivery required a new salt form and therefore a new crystallization procedure. This contribution describes development work to solve these issues and scaling up of the new process in the pilot plant.