6-fluoro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-aMine

Base Information

• Chemical Name: 6-fluoro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-aMine
• CAS No.: 944401-71-2
• Molecular Formula: C₁₁H₁₆BFN₂O₂
• Molecular Weight: 238.07
• Mol file: 944401-71-2.mol

Synonyms:2-AMINO-4-FLUORO PYRIDINE-5-BORONIC ACID PINACOL ESTER

Chemical Property of 6-fluoro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-aMine

Chemical Property:

• PSA: 57.37000
• LogP: 1.68330

Purity/Quality:

98% ^*data from raw suppliers

4-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine ＞95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-fluoro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-aMine

There total 3 articles about 6-fluoro-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-aMine 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: 100.0%

5-bromo-4-fluoro-pyridin-2-ylamine (944401-69-8) + bis(pinacol)diborane (73183-34-3) → 4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-71-2)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 110 ℃; for 2h; Sealed vessel;

Reference yield:

4-fluoropyridin-2-amine (944401-77-8) → 4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / acetonitrile / 5 h / 10 - 20 °C

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 110 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; potassium acetate; In 1,4-dioxane; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00167

Reference yield:

4-fluoropyridin-2-amine trifluoroacetate → 4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / acetonitrile / 2 h / 20 °C / Darkness

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere; Sealed tube

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

upstream raw materials:

5-bromo-4-fluoro-pyridin-2-ylamine

bis(pinacol)diborane

4-fluoropyridin-2-amine

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