4-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Base Information

• Chemical Name: 4-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
• CAS No.: 1201844-73-6
• Molecular Formula: C₁₅H₁₇BClNO₂
• Molecular Weight: 289.569
• DSSTox Substance ID: DTXSID60693639
• Wikidata: Q82622651
• Mol file: 1201844-73-6.mol

Synonyms:1201844-73-6;4-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline;4-Chloroquinoline-6-boronic acid pinacol ester;SCHEMBL1544664;DTXSID60693639;ANPKKHFSNJKOAM-UHFFFAOYSA-N;BYB84473;MFCD16987803;CS-0231910;FT-0765572;EN300-12579386;Z2044796327;4-chloro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Chemical Property of 4-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 289.1040866
• Heavy Atom Count: 20
• Complexity: 361

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloroquinoline-6-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=CN=C3C=C2)Cl

Technology Process of 4-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

There total 1 articles about 4-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

6-bromo-4-chloroquinoline (65340-70-7) + bis(pinacol)diborane (73183-34-3) → 4-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1201844-73-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 120 ℃; Inert atmosphere;

DOI:10.1021/jm200386s

Reference yield: 69.0%

N-(5-bromo-2-chloro-pyridine-3-yl)-4-fluorobenzenesulfonamide (887309-87-7) + 4-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1201844-73-6) → N-(2-chloro-5-(4-chloroquinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (1201841-63-5)

Guidance literature:

DOI:10.1021/jm200386s

Reference yield: 44.4%

N-(5-bromo-2-methoxypyridine-3-yl)-2,4-difluorobenzene sulfonyl chloride (1086063-46-8) + 4-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1201844-73-6) → N-(5-(4-chloroquinolin-6-yl)-2-methoxypyridine-3-yl)-2,4-difluorobenzenesulfonamide

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; In 1,4-dioxane; at 110 ℃; Inert atmosphere;

upstream raw materials:

6-bromo-4-chloroquinoline

bis(pinacol)diborane

Downstream raw materials:

N-(2-chloro-5-(4-chloroquinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

N-(2-chloro-5-(4-(4-(pyridin-4-ylmethyl)piperazin-1-yl)quinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

N-(2-chloro-5-(4-(piperidin-1-yl)quinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

N-(2-chloro-5-(4-(4-hydroxypiperidin-1-yl)quinolin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

Refernces

• 1、 Han, Jinsong,Chen, Ying,Yang, Chao,Liu, Ting,Wang, Mingping,Xu, Haojie,Zhang, Ling,Zheng, Canhui,Song, Yunlong,Zhu, Ju. "Structure-based optimization leads to the discovery of NSC765844, a highly potent, less toxic and orally efficacious dual PI3K/mTOR inhibitor". . p. 684 - 701. Retrieved 2016/07/21.
• 2、 Nishimura, Nobuko,Siegmund, Aaron,Liu, Longbin,Yang, Kevin,Bryan, Marian C.,Andrews, Kristin L.,Bo, Yunxin,Booker, Shon K.,Caenepeel, Sean,Freeman, Daniel,Liao, Hongyu,McCarter, John,Mullady, Erin L.,San Miguel, Tisha,Subramanian, Raju,Tamayo, Nuria,Wang, Ling,Whittington, Douglas A.,Zalameda, Leeanne,Zhang, Nancy,Hughes, Paul E.,Norman, Mark H.. "Phospshoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors: Discovery and structure-activity relationships of a series of quinoline and quinoxaline derivatives". experimental part. p. 4735 - 4751. Retrieved 2011/09/20.