N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

Base Information

• Chemical Name: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide
• CAS No.: 1083326-28-6
• Molecular Formula: C17H21BN2O4S
• Molecular Weight: 360.242
• Mol file: 1083326-28-6.mol

Synonyms:N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide;3-PhenylsulfonaMidopyridine-5-boronic acid pinacol ester, 96%

Chemical Property of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

Chemical Property:

• Boiling Point: 517.6±60.0 °C(Predicted)
• PKA: 7.63±0.40(Predicted)
• PSA: 85.90000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 3.33540
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

There total 5 articles about N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide 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: 87.0%

N-(5-bromopyridin-3-yl)benzenesulfonamide (1084-12-4) + bis(pinacol)diborane (73183-34-3) → N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-benzenesulfonamide (1083326-28-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.7b00222

Reference yield: 60.0%

potassium acetate (127-08-2) + N-(5-bromopyridin-3-yl)benzenesulfonamide (1084-12-4) + bis(pinacol)diborane (73183-34-3) → N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-benzenesulfonamide (1083326-28-6) + N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl)benzenesulfonamide, acetate salt

Guidance literature:

dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 100 ℃; for 3h; Sealed pressure tube;

Reference yield:

3-amino-5-bromopyridine (13535-01-8) → N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-benzenesulfonamide (1083326-28-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 20 °C / Inert atmosphere

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

With pyridine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dichloromethane;

DOI:10.1021/jm101582z

upstream raw materials:

N-(5-bromopyridin-3-yl)benzenesulfonamide

bis(pinacol)diborane

potassium acetate

3-amino-5-bromopyridine

Downstream raw materials:

N-{5-[3-(2-furanyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide

N-{5-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide

2-phenyl-N-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)acetamide

N-[5-(3-{4-[2-(methyloxy)phenyl]-1-piperazinyl}-6-quinoxalinyl)-3-pyridinyl]benzenesulfonamide

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