183208-34-6

Basic information

• Product Name: 5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE
• Synonyms: 5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE;5-Bromo-7-Aza-Indolin-2(3h)-One;2H-Pyrrolo[2,3-b]pyridin-2-one, 5-bromo-1,3-dihydro-;5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one;5-Bromo-1H-pyrrolo[2,3-b]...;5-Bromo-7-aza-2-oxindole;5-broMo-1H-pyrrolo[2;5-Bromo-2,3-dihydro-7-azaindole-2-one
• CAS NO: 183208-34-6
• Molecular Formula: C₇H₅BrN₂O
• Molecular Weight: 213.0314
• EINECS: 200-589-5
• Product Categories: CHIRAL CHEMICALS
• Mol File: 183208-34-6.mol

Chemical Properties

• Boiling Point: 387.799 °C at 760 mmHg
• Flash Point: 188.335 °C
• Appearance: /
• Density: 1.768 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 0.472mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 1.98±0.20(Predicted)
• CAS DataBase Reference: 5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE(183208-34-6)
• EPA Substance Registry System: 5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE(183208-34-6)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 183208-34-6(Hazardous Substances Data)

Usage

Chemical Properties

Pink powder

Upstream product

• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 206997-15-1 2-amino-5-bromo-3-pyridinecarbaldehyde 
• 13939-06-5 molybdenum hexacarbonyl 
• 92635-29-5 3,3,5-tribromo-2-oxindole 
• 271-63-6 7-Azaindole 
• 183208-32-4 3,3,5-Tribromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one 
• 113423-51-1 3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]-pyridin-2-one 

Downstream Products

• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 1111637-70-7 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-ylboronic acid 
• 1160112-78-6 5-iodo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one 
• 223646-08-0 5-phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one 
• 371758-71-3 5-(2-thienyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one 
• 223646-21-7 ethyl 2-oxo-2,3-dihydro-1H-pyrollo[2,3-b]pyridine-5-carboxylate 
• 189563-97-1 5-Vinyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one 

Relevant articles and documents

Substituted ring compound and its method and use thereof

The invention provides a substituted cyclic compound as well as a use method and application thereof. The compound is a compound as shown in a formula (I) or stereoisomers, stereomers, tautomers, nitric oxides, solvates, metabolites and pharmaceutically acceptable salts or prodrugs of the compound as shown in the formula (I). The invention further provides a medicament composition containing the compound. The compound and the medicament composition are capable of regulating the activity of protein kinase in a biological sample body and are used for protecting, treating or relieving proliferative diseases of patients. The formula (I) is as shown in the specification.

Design, synthesis and biological evaluation of 1H-pyrrolo[2,3-b]pyridine and 1H-pyrazolo[3,4-b]pyridine derivatives as c-Met inhibitors

Five novel 1H-pyrrolo[2,3-b]pyridine or 1H-pyrazolo[3,4-b]pyridine derivatives, with a methylene, sulfur, sulfoxide or cyclopropyl group as a linker, were designed, synthesized and biologically evaluated against c-Met and ALK. The development of these methods of compound synthesis may provide an important reference for the construction of novel 7-azaindole and 7-azaindazole derivatives with a single atom linker. The enzyme assay and cell assay in vitro showed that compound 9 displayed strong c-Met kinase inhibition with IC50 of 22.8 nM, moderate ALK kinase inhibition, and strong cell inhibition with MKN-45 IC50 of 329 nM and EBC-1 IC50 of 479 nM. In order to find the better candidate compounds, compounds 8, 9 and 10 have been selected as tool compounds for further optimization.

Application of 7-azaisatins in enantioselective Morita-Baylis-Hillman reaction

7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita-Baylis-Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized.

TRICYCLIC DLK INHIBITORS AND USES THEREOF

The invention relates to compounds of formula (I) and salts thereof, wherein ring A and R1-R2 have any of the values defined in the specification. The compounds and salts are useful for treating DLK mediated disorders. The invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable salt thereof, as well as methods of using said compounds, salts, or compositions as DLK inhibitors and for treating neurodegeneration diseases and disorders.

Synthesizing method of 5-bromine-1H-pyrrolo[2,3-b]pyridine

The invention particularly relates to a synthesizing method of 5-bromine-1H-pyrrolo[2,3-b]pyridine. The synthesizing method is characterized in that 1H-pyrrolo[2,3-b]pyridine is dissolved in a solvent to have bromination reaction with a brominating agent under 5-40 DEG C, and reductive dehalogenation is performed under 20-50 DEG C after the bromination reaction to obtain 5-bromine-1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-ketone; under the effect of a reducing agent, the 5-bromine-1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-ketone has reduction reaction in a certain solvent under 25-40 DEG C, and oxidative dehydrogenation is performed at 25-60 DEG C after the reduction reaction to obtain the 5-bromine-1H-pyrrolo[2,3-b]pyridine. The synthesizing method has the advantages that the method is simple in reaction step and mild in reaction condition, the four-step reaction is simplified into two one-pot two-step reactions, the treatment process is simplified, and the use amount of organic solvents is reduced.

Molybdenum hexacarbonyl mediated synthesis of indolin-2-one & azaindolin-2-one under catalyst free conditions

Syntheses of indolin-2-ones and azaindolin-2-ones have been realized. The strategy involves the formation of tosylhydrazone from tosylhydrazine and 2-amino aryl or pyridyl aldehydes/ketones which then undergo intramolecular aminocarbonylation to afford indolin-2-ones and azaindolin-2-ones. The generality of the method was demonstrated by synthesizing C3 substituted and unsubstituted indolin-2-one and azaindolin-2-one derivatives.

New bicyclic compounds as crac channel modulators

The present invention relates to novel compounds which are inhibitors of CRAC channel activity. This invention also relates to pharmaceutical compositions containing them, process for their preparation and their use in therapy.

3-SUBSTITUTED PYRAZOLES AND USE AS DLK INHIBITORS

The present invention provides for compounds of Formula (I) and various embodiments thereof, and compositions comprising compounds of Formula (I) and various embodiments thereof. (I) In compounds of Formula I, the groups R1, R2, R3, R4, R5, R6 and R7 have the meaning as described herein. The present invention also provides for methods of using compounds of Formula I and compositions comprising compounds of Formula (I) as DLK inhibitors and for treating neurodegeneration diseases and disorders.

SUBSTITUTED CYCLIC COMPOUNDS AND METHODS OF USE

The present invention provides novel substituted alkynyl compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

7-AZAINDOLE INHIBITORS OF CRAC

Disclosed are compounds of Formula (I), useful for treatment of autoimmune and inflammatory diseases associated with IL-2 inhibition via modulation of calcium release-activated calcium (CRAC) channels. Also disclosed are methods of making and using the compounds for treatment of diseases associated with CRAC channels.