2-(dimethoxymethyl)pyridine-5-boronic acid pinacol ester

Base Information

• Chemical Name: 2-(dimethoxymethyl)pyridine-5-boronic acid pinacol ester
• CAS No.: 1150632-93-1
• Molecular Formula: C14H22BNO4
• Molecular Weight: 279.16
• Hs Code.: 2933399990
• Mol file: 1150632-93-1.mol

Synonyms:6-(Dimethoxymethyl)pyridine-3-boronic acid pinacol ester;2-(dimethoxymethyl)pyridine-5-boronic acid pinacol ester;Pyridine, 2-(dimethoxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property of 2-(dimethoxymethyl)pyridine-5-boronic acid pinacol ester

Chemical Property:

• Boiling Point: 343.2±42.0 °C(Predicted)
• PKA: 4?+-.0.31(Predicted)
• PSA: 49.81000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 1.67220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

2-(Dimethoxymethyl)pyridine-5-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(dimethoxymethyl)pyridine-5-boronic acid pinacol ester

There total 3 articles about 2-(dimethoxymethyl)pyridine-5-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: 83.12%

5-bromo-2-(dimethoxymethyl)pyridine (1150632-94-2) + bis(pinacol)diborane (73183-34-3) → 2-(dimethoxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1150632-93-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; Inert atmosphere;

Reference yield:

5-bromo-pyridine-2-carbaldehyde (31181-90-5) → 2-(dimethoxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1150632-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / methanol / Reflux

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 50 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.201507045

Reference yield:

2-iodo-5-bromopyridine (223463-13-6) → 2-(dimethoxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1150632-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere

1.2: 0 - 20 °C

2.1: toluene-4-sulfonic acid / methanol / 16 h / Inert atmosphere

3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; isopropylmagnesium chloride; potassium acetate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; methanol;

upstream raw materials:

5-bromo-2-(dimethoxymethyl)pyridine

bis(pinacol)diborane

5-bromo-pyridine-2-carbaldehyde

2-iodo-5-bromopyridine

Downstream raw materials:

4,4-difluoro-8-{3,5-bis[2-(2-(2-hydroxyethoxy)ethoxy)ethoxy]phenyl}-2,6-bis[(2-dimethoxymethyl)pyridyl-5-yl]-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene

Refernces

• 1、 Neelakandan, Prakash P.,Jiménez, Azucena,Thoburn, John D.,Nitschke, Jonathan R.. "An Autocatalytic System of Photooxidation-Driven Substitution Reactions on a FeII4L6 Cage Framework". . p. 14378 - 14382. Retrieved 2015.
• 2、 -. "VINYL COMPOUNDS AS FGFR AND VEGFR INHIBITORS". Paragraph 0202; 0203. . Retrieved 2018/06/23.