942919-26-8

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• Synonyms: 1H-Pyrrolo[2,3-B]pyridine-4-boronic acid pinacol ester;1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;7-Azaindole-4-boronic acid pinacol ester;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;7-Azaindole-4-boronic aci...;4-(4,4,5,5-TetraMethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-;4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;2-dioxaborolan-2-yl)-1H-pyrrolo[2
• CAS NO: 942919-26-8
• Molecular Formula: C₁₃H₁₇BN₂O₂
• Molecular Weight: 244.1
• Mol File: 942919-26-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 405.7 °C at 760 mmHg
• Flash Point: 199℃
• Appearance: /
• Density: 1.15
• Vapor Pressure: 2.01E-06mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 13.71±0.40(Predicted)
• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-(942919-26-8)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-(942919-26-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45-24/25
• RIDADR: UN2811
• Hazardous Substances Data: 942919-26-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

Uses

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine is used in organic synthesis, in particular, that of novel potent and selective Tetrahydropyrazolo[1,5-a]pyrazines as ATR inhibitors.

InChI:InChI=1/C13H17BN2O2/c1-12(2)13(3,4)18-14(17-12)10-6-8-16-11-9(10)5-7-15-11/h5-8H,1-4H3,(H,15,16)

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 348640-06-2 4-bromo-7-azaindole 
• 55052-28-3 4-chloro-7-azaindole 

Downstream Products

• 1082444-87-8 tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate 
• 1352226-88-0 4-[4-[1-[[S(R)]-S-methylsulfonimidoyl]cyclopropyl]-6-[(3R)-3-methyl-4-morpholinyl]-2-pyrimidinyl]-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

Development and Scale-Up of an Improved Manufacturing Route to the ATR Inhibitor Ceralasertib

Ceralasertib is currently being evaluated in multiple phase I/II clinical trials for the treatment of cancer. Its structure, comprising a pyrimidine core decorated with a chiral morpholine, a cyclopropyl sulfoximine and an azaindole, makes it a challenging molecule to synthesize on a large scale. Several features of the medicinal chemistry and early development route make it unsuitable for the long-term commercial manufacture of the active pharmaceutical ingredient. We describe the investigation and development of a new and improved route which introduces the cyclopropyl moiety in a novel process from methyl 2,4-dibromobutyrate. Following construction of the pyrimidine ring, large-scale chlorination with phosphoryl chloride was performed with a safe and robust work-up. An SNAr reaction required an innovative work-up to remove the unwanted regio-isomer, and then a Baeyer-Villiger monooxygenase enzyme was used to enable asymmetric sulfur oxidation to a sulfoxide. A safe and scalable metal-free sulfoximine formation was developed, and then optimization of a Suzuki reaction enabled the manufacture of high-quality ceralasertib with excellent control of impurities and an overall yield of 16%.

TRIAZINE COMPOUNDS AS KINASE INHIBITORS

The present invention relates to triazine compounds that are useful as kinase inhibitors. More particularly, the present invention relates to morpholino substituted triazines, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative disorders including tumours and cancers as well as other disorders or conditions related to or associated with mTOR kinases or PI3 kinases. The compounds are of the formula (I)