2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL) PYRIDINE-4-BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL) PYRIDINE-4-BORONIC ACID PINACOL ESTER
• CAS No.: 880495-84-1
• Molecular Formula: C₁₈H₃₂BNO₃Si
• Molecular Weight: 349.353
• Mol file: 880495-84-1.mol

Synonyms:

Chemical Property of 2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL) PYRIDINE-4-BORONIC ACID PINACOL ESTER

Chemical Property:

• PSA: 40.58000
• LogP: 3.90260

Purity/Quality:

HPLC>98% ^*data from raw suppliers

2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL)PYRIDINE-4-BORONIC ACID PINACOL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL) PYRIDINE-4-BORONIC ACID PINACOL ESTER

There total 8 articles about 2-((TERT-BUTYLDIMETHYLSILYLOXY)METHYL) PYRIDINE-4-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:

4-bromo-2-(((tert-butyldimethylsilyl)oxy)methyl)pyridine (1307231-10-2) + bis(pinacol)diborane (73183-34-3) → 2-(((tert-Butyldimethylsilyl)oxy)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (880495-84-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; at 100 ℃; for 16h; Inert atmosphere;

Reference yield:

2-(((tert-butyldimethylsilyl)oxy)methyl)pyridine + bis(pinacol)diborane (73183-34-3) → 2-(((tert-Butyldimethylsilyl)oxy)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (880495-84-1) + 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1351378-73-8)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3-(2-(2-(dicyclohexylboraneyl)ethyl)phenyl)-1,10-phenanthroline; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In 1,4-dioxane; at 25 ℃; for 0.166667h; Inert atmosphere; Glovebox;

2-(((tert-butyldimethylsilyl)oxy)methyl)pyridine; In hexane; at 25 ℃; for 18h; Overall yield = 62 %; Overall yield = 0.22 g; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/jacs.9b03138

Reference yield:

C9H8ClNO4 (880495-83-0) → 2-(((tert-Butyldimethylsilyl)oxy)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (880495-84-1)

Guidance literature:

Multi-step reaction with 3 steps

1: LAH / tetrahydrofuran / 0.5 h / -78 °C

2: 96 percent / imidazole / dimethylformamide / 15 h / 20 °C

3: 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium*Cl^(1-); Pd(OAc)2 / tetrahydrofuran / 15 h / Heating

With 1H-imidazole; palladium diacetate; lithium aluminium tetrahydride; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.11.064

upstream raw materials:

2-(((tert-butyldimethylsilyl)oxy)methyl)-4-chloropyridine

bis(pinacol)diborane

C₉H₈ClNO₄

4-chloropicolinic acid

Refernces

• 1、 Yang, Lichen,Uemura, Nao,Nakao, Yoshiaki. "Meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst". supporting information. p. 7972 - 7979. Retrieved 2019/05/22.