N-(2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonaMide

Base Information

• Chemical Name: N-(2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonaMide
• CAS No.: 1083326-71-9
• Molecular Formula: C₁₅H₂₃BN₂O₅S
• Molecular Weight: 354.235
• Mol file: 1083326-71-9.mol

Synonyms:N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-3-yl)cyclopropanesulfonamide

Chemical Property of N-(2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonaMide

Chemical Property:

• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

N-(2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonaMide

There total 8 articles about N-(2-Methoxy-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonaMide 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: 97.0%

N-(5-bromo-2-methoxy-pyridine-3-yl)cyclopropyl-sulfonamide (1083326-05-9) + bis(pinacol)diborane (73183-34-3) → N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-3-yl)cyclopropanesulfonamide (1083326-71-9)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 80 ℃; for 2h;

Reference yield: 90.62%

→ N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-3-yl)cyclopropanesulfonamide (1083326-71-9)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 90 ℃; for 3h; Inert atmosphere;

Reference yield:

5-bromo-2-chloro-3-nitropyridine (67443-38-3) → N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-3-yl)cyclopropanesulfonamide (1083326-71-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium / 20 °C / Cooling

1.2: 17 h / 0 - 20 °C

2.1: iron; ammonium chloride / ethanol; water / 15 h / Reflux

3.1: pyridine / 23 h / 20 - 60 °C

4.1: potassium acetate / 1,4-dioxane / 2.5 h / 80 °C / Inert atmosphere

With pyridine; potassium acetate; sodium; iron; ammonium chloride; In 1,4-dioxane; ethanol; water;

upstream raw materials:

N-(5-bromo-2-methoxy-pyridine-3-yl)cyclopropyl-sulfonamide

bis(pinacol)diborane

5-bromo-2-(methyloxy)-3-pyridinamine

5-bromo-2-methoxy-3-nitropyridine

Downstream raw materials:

N-(5-(2-amino-1-(4-morpholinophenyl)-1H-benzo[d]imidazol-6-yl)-2-methoxypyridin-3-yl)cyclopropanesulfonamide

N-[5-{2-amino-3-[4-(ethylsulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]cyclopropanesulfonamide

Refernces

• 1、 Lin, Songwen,Wang, Chunyang,Ji, Ming,Wu, Deyu,Lv, Yuanhao,Sheng, Li,Han, Fangbin,Dong, Yi,Zhang, Kehui,Yang, Yakun,Li, Yan,Chen, Xiaoguang,Xu, Heng. "Discovery of new thienopyrimidine derivatives as potent and orally efficacious phosphoinositide 3-kinase inhibitors". supporting information. p. 637 - 646. Retrieved 2018/01/05.
• 2、 Yu, Tao,Li, Ning,Wu, Chengde,Guan, Amy,Li, Yi,Peng, Zhengang,He, Miao,Li, Jie,Gong, Zhen,Huang, Lei,Gao, Bo,Hao, Dongling,Sun, Jikui,Pan, Yan,Shen, Liang,Chan, Chichung,Lu, Xiulian,Yuan, Hongyu,Li, Yongguo,Li, Jian,Chen, Shuhui. "Discovery of Pyridopyrimidinones as Potent and Orally Active Dual Inhibitors of PI3K/mTOR". . p. 256 - 261. Retrieved 2018/03/21.