2-Amino-6-fluoro pyridine-5-boronic acid pinacol ester

Base Information

• Chemical Name: 2-Amino-6-fluoro pyridine-5-boronic acid pinacol ester
• CAS No.: 944401-67-6
• Molecular Formula: C11H16BFN2O2
• Molecular Weight: 238.068
• Hs Code.: 2934999090
• Mol file: 944401-67-6.mol

Synonyms:2-Amino-6-fluoro pyridine-5-boronic acid pinacol ester

Chemical Property of 2-Amino-6-fluoro pyridine-5-boronic acid pinacol ester

Chemical Property:

• PSA: 57.37000
• Density: 1.15
• LogP: 1.68330
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

98%Min ^*data from raw suppliers

6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Amino-6-fluoro pyridine-5-boronic acid pinacol ester

There total 2 articles about 2-Amino-6-fluoro pyridine-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: 35.0%

5-bromo-6-fluoropyridin-2-ylamine (944401-65-4) + bis(pinacol)diborane (73183-34-3) → 6-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-67-6)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 115 ℃; for 4.25h; Heating / reflux;

Reference yield:

6-fluoro-pyridin-2-ylamine (1597-32-6) → 6-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / acetic acid / 15 h / Darkness

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 4 h / 115 °C / Inert atmosphere

With N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; acetic acid;

Reference yield:

6-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-67-6) → C28H31FN6O3

Guidance literature:

Multi-step reaction with 3 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 90 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane; dichloromethane / 100 °C

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,2-dimethoxyethane / 0.33 h / 120 °C / Microwave irradiation

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 1: Suzuki coupling / 3: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.08.105

upstream raw materials:

5-bromo-6-fluoropyridin-2-ylamine

bis(pinacol)diborane

6-fluoro-pyridin-2-ylamine

Refernces

• 1、 -. "PYRIMIDINE DERIVATIVES USED AS PI-3 KINASE INHIBITORS". Page/Page column 101-102. . Retrieved 2010/11/28.