1146955-34-1

Basic information

• Product Name: 4-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole
• CAS NO: 1146955-34-1
• Molecular Weight: 236.701
• Mol File: 1146955-34-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole(1146955-34-1)
• EPA Substance Registry System: 4-chloro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole(1146955-34-1)

Safety Data

• Hazardous Substances Data: 1146955-34-1(Hazardous Substances Data)

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 13096-96-3 4-chloro-1H-indazole 

Downstream Products

• 956388-05-9 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 
• 1146955-35-2 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole 

Relevant articles and documents

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.