Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

Base Information

• Chemical Name: Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate
• CAS No.: 1083168-93-7
• Molecular Formula: C14H20BNO5
• Molecular Weight: 293.127
• Hs Code.: 2934999090
• Mol file: 1083168-93-7.mol

Synonyms:2-Methoxy-3-(carbomethoxy)pyridine-5-boronic acid, pinacol ester;2-Methoxy-3-(carbomethoxy)pyridine-5-boronic acid,pinacol ester;

Chemical Property of Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

Chemical Property:

• PSA: 66.88000
• LogP: 1.17600
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

2-Methoxy-3-(carbomethoxy)pyridine-5-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

There total 3 articles about Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate 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: 70.9%

methyl 5-bromo-2-methoxy-3-pyridinecarboxylate (122433-41-4) + bis(pinacol)diborane (73183-34-3) → methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate (1083168-93-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 65 ℃;

Reference yield:

2-methoxynicotinic acid methyl ester (67367-26-4) + bis(pinacol)diborane (73183-34-3) → methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate (1083168-93-7)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; at 120 ℃; for 1h;

DOI:10.1016/j.tet.2019.130836

Reference yield:

2-methoxynicotinic acid methyl ester (67367-26-4) + bis(pinacol)diborane (73183-34-3) → methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate (1083168-93-7) + methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1246765-27-4)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; at 20 ℃; for 24h; regioselective reaction; Glovebox; Sealed tube;

DOI:10.1039/c4ob01565g

upstream raw materials:

methyl 5-bromo-2-methoxy-3-pyridinecarboxylate

bis(pinacol)diborane

2-methoxynicotinic acid methyl ester

Refernces

• 1、 -. "AMINOIMIDAZOPYRIDINES AS KINASE INHIBITORS". Page/Page column 56. . Retrieved 2019/05/22.
• 2、 -. "MODULATORS OF CFTR". Page/Page column 104. . Retrieved 2009/01/20.