6-(4-MorpholinylMethyl)pyridine-3-boronic acid pinacol ester

Base Information

• Chemical Name: 6-(4-MorpholinylMethyl)pyridine-3-boronic acid pinacol ester
• CAS No.: 1160790-92-0
• Molecular Formula: C16H27BN2O4
• Molecular Weight: 304.197
• Hs Code.: 2934999090
• Mol file: 1160790-92-0.mol

Synonyms:6-(4-MorpholinylMethyl)pyridine-3-boronic acid pinacol ester;4-((5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)Methyl)Morpholine;6-(MorpholinoMethyl)pyridine-3-boronic Acid Pinacol Ester;4-[[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]methyl]-Morpholine

Chemical Property of 6-(4-MorpholinylMethyl)pyridine-3-boronic acid pinacol ester

Chemical Property:

• Boiling Point: 407.0±45.0 °C(Predicted)
• PKA: 5.54±0.10(Predicted)
• PSA: 43.82000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 1.15090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-((5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)methyl)morpholine is used as a reactant in the synthesis of antibacterial benzimidazole ureas.

Technology Process of 6-(4-MorpholinylMethyl)pyridine-3-boronic acid pinacol ester

There total 3 articles about 6-(4-MorpholinylMethyl)pyridine-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: 80.0%

4-[(5-bromo-2-pyridinyl)-methyl]morpholine (294851-95-9) + bis(pinacol)diborane (73183-34-3) → 4-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2-yl)methyl)morpholine (1160790-92-0)

Guidance literature:

With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 130 ℃; for 18h;

DOI:10.1021/jm500563g

Reference yield:

5-bromo-pyridine-2-carbaldehyde (31181-90-5) → 4-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2-yl)methyl)morpholine (1160790-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C

2: potassium acetate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride / 1,4-dioxane / 18 h / 130 °C

With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; potassium acetate; sodium tris(acetoxy)borohydride; In 1,4-dioxane; 1,2-dichloro-ethane;

DOI:10.1021/jm500563g

Reference yield:

→ 4-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2-yl)methyl)morpholine (1160790-92-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

upstream raw materials:

4-[(5-bromo-2-pyridinyl)-methyl]morpholine

bis(pinacol)diborane

5-bromo-pyridine-2-carbaldehyde

Refernces

• 1、 Grillot, Anne-Laure,Tiran, Arnaud Le,Shannon, Dean,Krueger, Elaine,Liao, Yusheng,Odowd, Hardwin,Tang, Qing,Ronkin, Steve,Wang, Tiansheng,Waal, Nathan,Li, Pan,Lauffer, David,Sizensky, Emmanuelle,Tanoury, Jerry,Perola, Emanuele,Grossman, Trudy H.,Doyle, Tim,Hanzelka, Brian,Jones, Steven,Dixit, Vaishali,Ewing, Nigel,Liao, Shengkai,Boucher, Brian,Jacobs, Marc,Bennani, Youssef,Charifson, Paul S.. "Second-generation antibacterial benzimidazole ureas: Discovery of a preclinical candidate with reduced metabolic liability". . p. 8792 - 8816. Retrieved 2015/03/14.