1-Isopropyl-6-oxo-1,6-dihydropyridine-3-boronic Acid Pinacol Ester

Base Information

• Chemical Name: 1-Isopropyl-6-oxo-1,6-dihydropyridine-3-boronic Acid Pinacol Ester
• CAS No.: 1349151-98-9
• Molecular Formula: C14H24BNO4
• Molecular Weight: 263.145
• Mol file: 1349151-98-9.mol

Synonyms:1-Isopropyl-6-oxo-1,6-dihydropyridine-3-boronic Acid Pinacol Ester;1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

Chemical Property of 1-Isopropyl-6-oxo-1,6-dihydropyridine-3-boronic Acid Pinacol Ester

Chemical Property:

• PSA: 40.46000
• LogP: 1.72840
• Storage Temp.: 2-8°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Isopropyl-6-oxo-1,6-dihydropyridine-3-boronic Acid Pinacol Ester

There total 3 articles about 1-Isopropyl-6-oxo-1,6-dihydropyridine-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: 85.0%

5-bromo-1-isopropylpyridine-2(1H)-one (851087-08-6) + bis(pinacol)diborane (73183-34-3) → 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2(1H)-one (1349151-98-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 2h; Reagent/catalyst;

Reference yield:

5-bromopyridin-2(1H)-one (13466-38-1,49843-23-4) → 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2(1H)-one (1349151-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.5 h / 20 °C

1.2: 64 h / Reflux

2.1: potassium acetate / Pd(dppf)Cl₂*CH₃CN / 1,4-dioxane / 16.25 h / 100 °C / Inert atmosphere

With potassium tert-butylate; potassium acetate; Pd(dppf)Cl₂*CH₃CN; In 1,4-dioxane; 1,2-dimethoxyethane;

Reference yield:

5-bromopyridin-2-ol (13466-38-1) → 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2(1H)-one (1349151-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.5 h

1.2: 65 h / Reflux

2.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere

With potassium tert-butylate; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; 1,2-dimethoxyethane;

upstream raw materials:

5-bromo-1-isopropylpyridine-2(1H)-one

bis(pinacol)diborane

5-bromopyridin-2-ol

5-bromopyridin-2(1H)-one

Downstream raw materials:

5-[5-amino-6-[5-[2-methyl-4-[[[(3S)-tetrahydrofuran-3-yl]amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-1-isopropylpyridin-2-one

5-[5-amino-6-[5-[3-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-1-isopropylpyridin-2-one

5-[5-amino-6-[5-[3-(bromomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-1-isopropylpyridin-2-one

tert-butyl N-[3-[5-[4-(bromomethyl)-2-methylphenyl]-1,3,4-oxadiazol-2-yl]-5-(1-isopropyl-6-oxo-3-pyridyl)pyrazin-2-yl]-N-tert-butoxycarbonylcarbamate

Refernces

• 1、 -. "PYRIDINONE DERIVATIVES AND THEIR USE AS SELECTIVE ALK-2 INHIBITORS". Page/Page column 48-49. . Retrieved 2019/06/11.
• 2、 -. "Substituted thiazole derivative and application thereof". Paragraph 0150-0152; 0159-0160. . Retrieved 2019/02/13.