1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

Base Information

• Chemical Name: 1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate
• CAS No.: 1266727-99-4
• Molecular Formula: C₂₆H₃₉F₂NO₅Si
• Molecular Weight: 511.682
• Mol file: 1266727-99-4.mol

Synonyms:1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

Chemical Property of 1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

There total 2 articles about 1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate 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: 70.0%

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1194488-90-8) + [(2-bromo-4,5-difluorobenzyl)oxy](tert-butyl)dimethylsilane (1266727-98-3) → 1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate (1266727-99-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In ethanol; water; toluene; at 80 ℃; for 14h;

DOI:10.1016/j.bmcl.2011.10.013

Reference yield:

2-bromo-4,5-difluorobenzoic acid (64695-84-7) → 1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate (1266727-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethylsulfide borane complex / tetrahydrofuran / 2.5 h / Reflux

2: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

3: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; ethanol; water / 14 h / 80 °C / Inert atmosphere

With 1H-imidazole; dimethylsulfide borane complex; sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;

Reference yield:

1-tert-butyl 3-ethyl 4-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-difluorophenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate (1266727-99-4) → tert-butyl (cis-1,3')-3'-{[benzyl(cyclopropyl)amino]carbonyl}-5,6-difluoro-1'H,3Hspiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2.1: isopropylmagnesium chloride / tetrahydrofuran / 0.33 h / 0 °C

2.2: 14 h / 0 - 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 60 °C

With tetrabutyl ammonium fluoride; isopropylmagnesium chloride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

2-bromo-4,5-difluorobenzoic acid

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

[(2-bromo-4,5-difluorobenzyl)oxy](tert-butyl)dimethylsilane