4-{ [tert-butyl(dimethyl)silyl]oxy}-N¹-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine

Base Information

• Chemical Name: 4-{ [tert-butyl(dimethyl)silyl]oxy}-N¹-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine
• CAS No.: 1345687-91-3
• Molecular Formula: C₂₅H₃₈N₂O₄Si
• Molecular Weight: 458.673

Synonyms:4-{ [tert-butyl(dimethyl)silyl]oxy}-N¹-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine

Chemical Property of 4-{ [tert-butyl(dimethyl)silyl]oxy}-N¹-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine

Chemical Property:

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Technology Process of 4-{ [tert-butyl(dimethyl)silyl]oxy}-N¹-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine

There total 4 articles about 4-{ [tert-butyl(dimethyl)silyl]oxy}-N¹-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine 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: 74.0%

4-{[tert-butyl(dimethyl)silyl]oxy}-2-nitro-N-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}aniline (1345687-89-9) → 4-{ [tert-butyl(dimethyl)silyl]oxy}-N1-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine (1345687-91-3)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In ethanol; at 20 ℃; for 2h;

Reference yield:

4-hydroxy-2-nitroaniline (610-81-1) → 4-{ [tert-butyl(dimethyl)silyl]oxy}-N1-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine (1345687-91-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / dichloromethane / 20 °C / Cooling with ice

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine / toluene / 0.17 h / 110 °C / Inert atmosphere

3: hydrogen; palladium(II) hydroxide / ethanol / 2 h / 20 °C

With 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; hydrogen; palladium(II) hydroxide; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; sodium t-butanolate; In ethanol; dichloromethane; toluene;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4-{ [tert-butyl(dimethyl)silyl]oxy}-N1-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}benzene-1,2-diamine (1345687-91-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / dichloromethane / 20 °C / Cooling with ice

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine / toluene / 0.17 h / 110 °C / Inert atmosphere

3: hydrogen; palladium(II) hydroxide / ethanol / 2 h / 20 °C

With 1H-imidazole; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; hydrogen; palladium(II) hydroxide; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; sodium t-butanolate; In ethanol; dichloromethane; toluene;

upstream raw materials:

4-hydroxy-2-nitroaniline

4-{[tert-butyl(dimethyl)silyl]oxy}-2-nitro-N-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}aniline

tert-butyldimethylsilyl chloride

4-{[tert-butyl(dimethyl)silyl]oxy}-2-nitroaniline

Downstream raw materials:

1-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}-1H-benzimidazol-5-ol

1-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}-1H-benzimidazol-5-yl trifluoromethanesulfonate

5-pyridin-4-yl-1-{4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]phenyl}-1H-benzimidazole

2-(4-{5-[6-(morpholin-4-ylcarbonyl)pyridin-3-yl]-1H-benzimidazol-1-yl}phenoxy)ethanol

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