6-(tert-Butyloxycarbonyl-methylamino)pyridine-3-boronic acid pinacol ester

Base Information

• Chemical Name: 6-(tert-Butyloxycarbonyl-methylamino)pyridine-3-boronic acid pinacol ester
• CAS No.: 1032758-87-4
• Molecular Formula: C₁₇H₂₇BN₂O₄
• Molecular Weight: 334.223
• Hs Code.: 2934999090
• Mol file: 1032758-87-4.mol

Synonyms:TERT-BUTYL N-METHYL-N-[5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDIN-2-YL]CARBAMATE;

Chemical Property of 6-(tert-Butyloxycarbonyl-methylamino)pyridine-3-boronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 8.58E-08mmHg at 25°C
• Boiling Point: 435.7ºC at 760 mmHg
• Flash Point: 217.3ºC
• PSA: 60.89000
• Density: 1.09g/cm3
• LogP: 2.75210

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-(tert-Butyloxycarbonyl-methylamino)pyridine-3-boronic acid pinacol ester

There total 3 articles about 6-(tert-Butyloxycarbonyl-methylamino)pyridine-3-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:

bis(pinacol)diborane (73183-34-3) + 5-bromo-2-(N-methyl-N-(t-butoxycarbonyl)amino)pyridine (227939-01-7) → methyl-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-carbamic acid tert-butyl ester (1032758-87-4)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dichloromethane; dimethyl sulfoxide; at 80 ℃;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-carbamic acid tert-butyl ester (1032758-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 14 h / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium hexamethyldisilazane; In tetrahydrofuran; dimethyl sulfoxide;

Reference yield:

5-bromo-N-methylpyridin-2-amine (84539-30-0) → methyl-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-carbamic acid tert-butyl ester (1032758-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / dimethyl sulfoxide / 14 h / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium hexamethyldisilazane; In tetrahydrofuran; dimethyl sulfoxide;

upstream raw materials:

bis(pinacol)diborane

5-bromo-2-(N-methyl-N-(t-butoxycarbonyl)amino)pyridine

di-tert-butyl dicarbonate

5-bromo-N-methylpyridin-2-amine

Refernces

• 1、 -. "THIAZOLOPYRIMIDINE PI3K INHIBITOR COMPOUNDS AND METHODS OF USE". Page/Page column 84. . Retrieved 2009/05/29.