1146955-35-2

Basic information

• Product Name: 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole
• Synonyms: 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole
• CAS NO: 1146955-35-2
• Molecular Formula: C₁₈H₂₅BN₂O₃
• Molecular Weight: 328.2137
• Mol File: 1146955-35-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 497.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 0.79±0.30(Predicted)
• CAS DataBase Reference: 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole(1146955-35-2)
• EPA Substance Registry System: 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole(1146955-35-2)

Safety Data

• Hazardous Substances Data: 1146955-35-2(Hazardous Substances Data)

Usage

General Description

2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole is a complex chemical compound with a molecular formula C20H23BN2O2. It is an indazole derivative that contains a tetrahydro-2H-pyran-2-yl group and a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group. 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole is commonly used in medicinal chemistry and pharmaceutical research as a building block for the synthesis of potential drug candidates. It has shown potential for pharmacological activities including anti-inflammatory, anti-cancer, and anti-microbial properties. Additionally, the boron-containing group in the molecule can be used for Suzuki-Miyaura coupling reactions, making this compound a valuable tool in organic synthesis. Due to its complex structure and potential biological activities, 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole is an important target for further research and development in the field of medicinal chemistry.

Upstream product

• 1266386-31-5 4-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole 
• 73183-34-3 bis(pinacol)diborane 
• 110-87-2 3,4-dihydro-2H-pyran 
• 186407-74-9 4-bromoindazole 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 41748-71-4 4-aminoindazole 
• 603-83-8 3-nitro-o-tolylamine 
• 2942-40-7 nitro-4 indazole 
• 885618-33-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 
• 1137278-45-5 4-chloro-1-(tetrahydro-2H-pyran-2-yl)-2H-indazole 
• 1146955-34-1 4-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole 
• 13096-96-3 4-chloro-1H-indazole 

Downstream Products

• 1391926-36-5 C₂₈H₃₁N₇O₄ 
• 1391926-60-5 C₃₁H₃₀N₆O₅S 
• 1391926-39-8 C₂₉H₃₃N₇O₄ 
• 1391926-34-3 4-(4-(benzylthio)-6-(2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl)-1,3,5-triazin-2-yl)morpholine 
• 1391926-38-7 C₃₁H₃₀N₆O₃S 
• 1391926-45-6 C₂₇H₃₀N₆O₃ 
• 1391925-55-5 3-((4-(1H-indazol-4-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)-N,N-dimethylbenzamide 
• 1542268-06-3 (1r,4r)-4-((4-(2H-indazol-4-yl)-6-morpholino-1,3,5-triazine-2-yl)oxy)-N,N-dimethycyclohexanecarboxamide hydrochloride 
• 1542268-07-4 C₂₈H₃₇N₇O₄ 

Relevant articles and documents

Discovery of Novel and Orally Bioavailable Inhibitors of PI3 Kinase Based on Indazole Substituted Morpholino-Triazines

A new class of potent PI3Kα inhibitors is identified based on aryl substituted morpholino-triazine scaffold. The identified compounds showed not only a high level of enzymatic and cellular potency in nanomolar range but also high oral bioavailability. The three lead molecules (based on their in vitro potency) when evaluated further for in vitro metabolic stability as well as pharmacokinetic profile led to the identification of 26, as a candidate for further development. The IC50 and EC50 value of 26 is 60 and 500 nM, respectively, for PI3Kα enzyme inhibitory activity and ovarian cancer (A2780) cell line. The identified lead also showed a high level of microsomal stability and minimal inhibition activity for CYP3A4, CYP2C19, and CYP2D6 at 10 μM concentrations. The lead compound 26, demonstrated excellent oral bioavailability with an AUC of 5.2 μM at a dose of 3 mpk in mice and found to be well tolerated in mice when dosed at 30 mpk BID for 5 days.

A practical synthesis of a PI3K inhibitor under noncryogenic conditions via functionalization of a lithium triarylmagnesiate intermediate

We report a practical synthesis of PI3K inhibitor GDC-0941. The synthesis was achieved using a convergent approach starting from a thienopyrimidine intermediate through a sequence of formylation and reductive amination followed by Suzuki-Miyaura cross-coupling. Metalation of the thienopyrimidine intermediate involving the intermediacy of triarylmagnesiates allowed formylation under noncryogenic conditions to produce the corresponding aldehyde. We also investigated aminoalkylation via a benzotriazolyl-piperazine substrate as an alternative to the reductive amination route. We evaluated both palladium and nickel catalyzed processes for the borylation and Suzuki-Miyaura cross-coupling. Final deprotection and salt formation afforded the API.

METHOD FOR MANUFACTURING A BORONIC ACID ESTER COMPOUND

The present invention relates to a method for manufacturing a boronic acid ester compound, characterized by reacting an aryl halide compound and a diboron ester compound in the presence of a nitrogen-containing organic base, a nickel catalyst, a phosphine compound and a solvent. According to the manufacturing method of the present invention, even if a nickel catalyst is used as the catalyst, a desired boronic acid ester compound can be obtained in a sufficiently high yield. Furthermore, even if aryl chloride or aryl bromide having relatively low price and low reactivity, was used as the aryl halide compound, a desired boronic acid ester compound can be obtained in a sufficiently high yield.