2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Base Information

• Chemical Name: 2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 1083168-87-9
• Molecular Formula: C₁₃H₂₀BNO₃
• Molecular Weight: 249.118
• Hs Code.: 2933399990
• Mol file: 1083168-87-9.mol

Synonyms:2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;6-Methoxy-2-picoline-4-boronic acid, pinacol ester

Chemical Property of 2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property:

• Boiling Point: 346.2±42.0 °C(Predicted)
• PKA: 3.30±0.10(Predicted)
• PSA: 40.58000
• Density: 1.05±0.1 g/cm3(Predicted)
• LogP: 1.69780

Purity/Quality:

98%min ^*data from raw suppliers

2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine is an intermediate used to prepare pyridine compounds as modulators of cystic fibrosis transmembrane conductance regulator (CFTR) useful in treatment of CFTR-mediated diseases.

Technology Process of 2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

There total 2 articles about 2-Methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 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: 50.0%

2-methoxy-6-methyl-pyridine (63071-03-4) + bis(pinacol)diborane (73183-34-3) → 2-methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1083168-87-9)

Guidance literature:

With C₃₉H₅₉Br₂CoN₇Si₂; sodium triethylborohydride; cyclohexene; In tetrahydrofuran; at 100 ℃; for 24h; regioselective reaction; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1002/chem.201605937

Reference yield:

4-bromo-2-methoxy-6-methylpyridine (1083169-00-9) + bis(pinacol)diborane (73183-34-3) → 2-methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1083168-87-9)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80 ℃; for 18h;

Reference yield:

2-methoxy-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1083168-87-9) → (2-methoxy-6-methylpyridin-4-yl)boronic acid (1309443-98-8)

Guidance literature:

at 20 ℃;

upstream raw materials:

4-bromo-2-methoxy-6-methylpyridine

bis(pinacol)diborane

2-methoxy-6-methyl-pyridine

Downstream raw materials:

(2-methoxy-6-methylpyridin-4-yl)boronic acid

Refernces

• 1、 Ren, Hailong,Zhou, Yu-Peng,Bai, Yunping,Cui, Chunming,Driess, Matthias. "Cobalt-Catalyzed Regioselective Borylation of Arenes: N-Heterocyclic Silylene as an Electron Donor in the Metal-Mediated Activation of C?H Bonds". supporting information. p. 5663 - 5667. Retrieved 2017/04/28.
• 2、 -. "MODULATORS OF CFTR". Page/Page column 99. . Retrieved 2009/01/20.