338760-45-5

Basic information

• Product Name: 1H-INDOLE-3-CARBOXALDEHYDE, 4-BROMO-1-METHYL-
• Synonyms: 1H-INDOLE-3-CARBOXALDEHYDE, 4-BROMO-1-METHYL-;4-BroMo-1-Methyl-1H-indole-3-carbaldehyde
• CAS NO: 338760-45-5
• Molecular Formula: C₁₀H₈BrNO
• Molecular Weight: 238.08062
• Mol File: 338760-45-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-INDOLE-3-CARBOXALDEHYDE, 4-BROMO-1-METHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE-3-CARBOXALDEHYDE, 4-BROMO-1-METHYL-(338760-45-5)
• EPA Substance Registry System: 1H-INDOLE-3-CARBOXALDEHYDE, 4-BROMO-1-METHYL-(338760-45-5)

Safety Data

• Hazardous Substances Data: 338760-45-5(Hazardous Substances Data)

Usage

Uses

4-Bromo-1-methyl-1H-indole-3-carbaldehyde is used in preparation of 3-substituted 1H-indoles and 1H-pyrrolopyridines as mTOR kinase and PI3 kinase inhibitors.

Upstream product

• 98600-34-1 4-bromo-1H-indole-3-carbaldehyde 
• 74-88-4 methyl iodide 
• 52488-36-5 4-bromo-1H-indole 
• 590417-55-3 4-bromo-1-methyl-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1200525-25-2 4-(4-isopropoxy-phenyl)-1-methyl-1H-indole-3-carboxylaldehyde 
• 1200527-55-4 4-(4-methoxyphenyl)-1-methyl-1H-indole-3-carbaldehyde 

Relevant articles and documents

Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.

1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors

KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase.