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

General 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 chemical compound with a complex structure. It is a methyl ester derivative of a carboxylic acid containing a fluoro-substituted indole ring. The compound also contains a dihydro-1,3-dioxo-2H-isoindol-2-yl group connected to an ethyl chain. The presence of these functional groups gives the compound potential for biological activity, particularly in pharmaceutical applications. Additionally, the fluoro substitution can have implications for the compound's physicochemical properties and potential interactions in biological systems.

Upstream product

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

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 

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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.