3-Amino-2-chloropyridine-5-boronic acid, pinacol ester

Base Information

• Chemical Name: 3-Amino-2-chloropyridine-5-boronic acid, pinacol ester
• CAS No.: 1073354-96-7
• Molecular Formula: C11H18BClN2O3
• Molecular Weight: 254.524
• Hs Code.: 2934999090
• Mol file: 1073354-96-7.mol

Synonyms:3-AMINO-2-CHLOROPYRIDINE-5-BORONIC ACID, PINACOL ESTER;3-AMino-2-chloropyridin-5-ylboronic acid pinacol ester

Chemical Property of 3-Amino-2-chloropyridine-5-boronic acid, pinacol ester

Chemical Property:

• Boiling Point: 398.1±42.0 °C(Predicted)
• PKA: 2.44±0.10(Predicted)
• PSA: 57.37000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 2.19760
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

98%min ^*data from raw suppliers

3-Amino-2-chloropyridine-5-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Amino-2-chloropyridine-5-boronic acid, pinacol ester

Technology Process of 3-Amino-2-chloropyridine-5-boronic acid, pinacol ester

There total 4 articles about 3-Amino-2-chloropyridine-5-boronic acid, pinacol ester 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: 80.0%

3-amino-5-bromo-2-chloropyridine (588729-99-1) + bis(pinacol)diborane (73183-34-3) → 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (1073354-96-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.6b00167

Reference yield:

5-bromo-2-chloro-3-nitropyridine (67443-38-3) → 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (1073354-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere

2: palladium on activated charcoal / methanol / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; potassium acetate; In 1,4-dioxane; methanol;

DOI:10.1021/acsmedchemlett.8b00002

Reference yield:

C11H14BClN2O4 → 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (1073354-96-7)

Guidance literature:

With palladium on activated charcoal; In methanol; at 20 ℃;

DOI:10.1021/acsmedchemlett.8b00002

upstream raw materials:

3-amino-5-bromo-2-chloropyridine

bis(pinacol)diborane

5-bromo-2-chloro-3-nitropyridine

Downstream raw materials:

N-(2-chloro-5-(4-((3-chloro-4-fluorophenyl)amino)quinazolin-6-yl)pyridin-3-yl)methanesulfonamide

2,6-dichloro-N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)benzenesulfonamide

N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)-2-fluorobenzenesulfonamide

N-{2-chloro-5-[5-methyl-3-(2-trimethylsilylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]pyridin-3-yl}benzenesulphonamide

Refernces

• 1、 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". supporting information. p. 256 - 261. Retrieved 2018/03/21.
• 2、 -. "PI3K/M TOR INHIBITORS". Page/Page column 143-144. . Retrieved 2010/04/03.