Methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

Base Information

• Chemical Name: Methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate
• CAS No.: 1246765-27-4
• Molecular Formula: C14H20BNO5
• Molecular Weight: 293.127
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50704849
• Nikkaji Number: J3.025.867C
• Wikidata: Q82637429
• Mol file: 1246765-27-4.mol

Synonyms:1246765-27-4;Methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate;methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate;2-Methoxy-3-(methoxycarbonyl)pyridine-6-boronic acid pinacol ester;SCHEMBL423702;DTXSID50704849;WZB76527;AKOS015999830;Methyl2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate;AT14585;BP-11647;BS-19636;CS-0175732;FT-0757882;methyl 2-methoxy-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinate;Methyl 2-methoxy-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)nicotinate;2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-3-pyridinecarboxylic acid methyl ester

Chemical Property of Methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

Chemical Property:

• PSA: 66.88000
• LogP: 1.17600
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 293.1434529
• Heavy Atom Count: 21
• Complexity: 385

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=NC(=C(C=C2)C(=O)OC)OC

Technology Process of Methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

There total 4 articles about Methyl 2-methoxy-6-(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: 73.6%

methyl 6-chloro-2-methoxypyridine-3-carboxylate (65515-32-4) + bis(pinacol)diborane (73183-34-3) → methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1246765-27-4)

Guidance literature:

methyl 6-chloro-2-methoxypyridine-3-carboxylate; bis(pinacol)diborane; With potassium acetate; In 1,2-dimethoxyethane; for 0.5h; Inert atmosphere;

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2011.10.052

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

Reference yield:

2,6-dichloropyridine-3-carboxylic acid (38496-18-3) → methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1246765-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfuric acid / 20 h / Reflux

2.1: dichloromethane / 16 h / -5 - 20 °C

3.1: potassium acetate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere

3.2: 12 h / Inert atmosphere; Reflux

With sulfuric acid; potassium acetate; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1016/j.tetlet.2011.10.052

upstream raw materials:

methyl 6-chloro-2-methoxypyridine-3-carboxylate

bis(pinacol)diborane

2,6-dichloropyridine-3-carboxylic acid

methyl 2,6-dichloronicotinate

Downstream raw materials:

methyl 6-(1-(4-cyano-3-methylphenyl)-5-cyclopentyl-4,5-dihydro-1H-pyrazol-3-yl)-2-methoxynicotinate

(R)-methyl 6-(1-(4-cyano-3-methylphenyl)-5-cyclopentyl-4,5-dihydro-1H-pyrazol-3-yl)-2-methoxynicotinate

(R)-6-(1-(4-cyano-3-methylphenyl)-5-cyclopentyl-4,5-dihydro-1H-pyrazol-3-yl)-2-methoxynicotinic acid

C₁₆H₁₆N₂O₆

Refernces

• 1、 Boos, Charles,Bowles, Daniel M.,Cai, Cuiman,Casimiro-Garcia, Agustin,Chen, Xiangyang,Hulford, Catherine A.,Jennings, Sandra M.,Jason Kiser,Piotrowski, David W.,Sammons, Matthew,Wade, Robert A.. "Synthesis and cross coupling of a highly substituted 2-pyridylboronate: Application to the large scale synthesis of a mineralocorticoid antagonist". experimental part. p. 7025 - 7029. Retrieved 2012/01/05.