[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)- pyridin-3-yl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)- pyridin-3-yl]-carbamic acid tert-butyl ester
• CAS No.: 1171897-39-4
• Molecular Formula: C16H25BN2O4
• Molecular Weight: 320.196
• Mol file: 1171897-39-4.mol

Synonyms:[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)- pyridin-3-yl]-carbamic acid tert-butyl ester;tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate

Chemical Property of [5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)- pyridin-3-yl]-carbamic acid tert-butyl ester

Chemical Property:

• Boiling Point: 400.7±30.0 °C(Predicted)
• PKA: 13.04±0.70(Predicted)
• PSA: 69.68000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 2.80080
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

≥99% ^*data from raw suppliers

tert-Butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)- pyridin-3-yl]-carbamic acid tert-butyl ester

There total 4 articles about [5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)- pyridin-3-yl]-carbamic acid tert-butyl 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: 70.0%

bis(pinacol)diborane (73183-34-3) + (5-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester (361550-43-8) → tert-butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)carbamate (1171897-39-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 20h; Inert atmosphere; Sealed tube;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)carbamate (1171897-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 20 °C

1.2: 24 h / 20 °C

2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 0.75 h / 120 °C / Inert atmosphere; Microwave irradiation

With potassium acetate; sodium hexamethyldisilazane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane;

Reference yield:

3-amino-5-bromopyridine (13535-01-8) → tert-butyl (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)carbamate (1171897-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 20 °C

1.2: 24 h / 20 °C

2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 0.75 h / 120 °C / Inert atmosphere; Microwave irradiation

With potassium acetate; sodium hexamethyldisilazane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane;

upstream raw materials:

bis(pinacol)diborane

(5-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

3-amino-5-bromopyridine

Downstream raw materials:

tert-butyl 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-ylcarbamate

N-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)methanesulfonamide

1-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)urea

N-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)sulfamide

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