1201189-40-3

Upstream product

• 111454-57-0 3-bromo-5-methoxy-1-methyl-1H-indole 
• 73183-34-3 bis(pinacol)diborane 
• 1006-94-6 5-methoxylindole 
• 2521-13-3 5-methoxy-N-methylindole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 1350378-35-6 1-(5-(5-fluoro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol 

Relevant academic research and scientific papers

Organophosphorus-catalyzed relay oxidation of H-Bpin: electrophilic C-H borylation of heteroarenes

A nontrigonal phosphorus triamide (1, P{N[o-NMe-C6H4]2}) is shown to catalyze C-H borylation of electron-rich heteroarenes with pinacolborane (HBpin) in the presence of a mild chloroalkane reagent. C-H borylation proceeds for a range of electron-rich heterocycles including pyrroles, indoles, and thiophenes of varied substitution. Mechanistic studies implicate an initial P-N cooperative activation of HBpin by1to giveP-hydrido diazaphospholene2, which is diverted by Atherton-Todd oxidation with chloroalkane to generateP-chloro diazaphospholene3. DFT calculations suggest subsequent oxidation of pinacolborane by3generates chloropinacolborane (ClBpin) as a transient electrophilic borylating species, consistent with observed substituent effects and regiochemical outcomes. These results illustrate the targeted diversion of established reaction pathways in organophosphorus catalysis to enable a new mode of main group-catalyzed C-H borylation.

Zinc catalysed C3-H borylation of indoles and 1,1-diboration of terminal alkynes

A low catalyst loading Zn(OTf)2-catalysed C3-H borylation of indoles with pinacolborane was developed. This transformation represents the use of an abundant, cheap and environmentally benign zinc catalyst in catalytic direct aromatic C-H borylation and offers a simple and prompt route towards the synthesis of C3-borylated indoles. The 1,1-diboration of terminal alkynes was also achieved using the same catalytic system to produce 1,1-diborylated alkenes.

Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis

The potential advantages of using arylboronic esters as boron sources in C-H borylation are discussed. The concept is showcased using commercially available 2-mercaptopyridine as a metal-free catalyst for the transfer borylation of heteroarenes using arylboronates as borylation agents. The catalysis shows a unique functional group tolerance among C-H borylation reactions, tolerating notably terminal alkene and alkyne functional groups. The mechanistic investigation is also described.

Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts

A practical and scalable metal-free catalytic method for the borylation and borylative dearomatization of heteroarenes has been developed. This synthetic method uses inexpensive and conveniently synthesizable bench-stable precatalysts of the form 1-NHR2-2-BF3-C6H4, commercially and synthetically accessible heteroarenes as substrates, and pinacolborane as the borylation reagent. The preparation of several borylated heterocycles on 2 and 50 g scales was achieved under solvent-free conditions without the use of Schlenk techniques or a glovebox. A kilogram-scale borylation of one of the heteroarene substrates was also achieved using this cost-effective green methodology to exemplify the fact that our methodology can be conveniently implemented in fine chemical industries.

PYRROLOPYRIDINE AND PYRROLOPYRIMIDINE INHIBITORS OF KINASES

The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein A, B, R1, R2, R3, R4a, R5, and Z are defined in the description. The present invention relates also to methods of making said compounds, and compositions containing said compounds which are useful for inhibiting kinases such as aurora.