[3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine

Base Information

• Chemical Name: [3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine
• CAS No.: 915410-96-7
• Molecular Formula: C₂₄H₂₇BN₂O₃
• Molecular Weight: 402.301
• Mol file: 915410-96-7.mol

Synonyms:[3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine

Chemical Property of [3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine

There total 5 articles about [3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine 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: 73.0%

(3-benzyloxy-5-bromo-phenyl)-pyridin-3-yl-amine (915410-94-5) + bis(pinacol)diborane (73183-34-3) → [3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine (915410-96-7)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80 ℃; for 20h;

Reference yield:

3,5-dibromonitrobenzene (6311-60-0) → [3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine (915410-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutylammomium bromide; oxygen; potassium hydroxide / tetramethylurea / 0.12 h / 20 °C

2: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 90 °C / Inert atmosphere

3: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane; potassium acetate / dimethyl sulfoxide / 80 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane; tetrabutylammomium bromide; oxygen; potassium acetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; potassium hydroxide; sodium t-butanolate; In dimethyl sulfoxide; toluene; tetramethylurea; 2: Buchwald-Hartwig amination / 3: Suzuki-Miyura coupling;

DOI:10.1021/jm100659v

Reference yield:

1-(benzyloxy)-3,5-dibromobenzene (128924-01-6) → [3-benzyloxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine (915410-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 90 °C / Inert atmosphere

2: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane; potassium acetate / dimethyl sulfoxide / 80 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane; potassium acetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In dimethyl sulfoxide; toluene; 1: Buchwald-Hartwig amination / 2: Suzuki-Miyura coupling;

DOI:10.1021/jm100659v

upstream raw materials:

(3-benzyloxy-5-bromo-phenyl)-pyridin-3-yl-amine

bis(pinacol)diborane

3,5-dibromonitrobenzene

1-(benzyloxy)-3,5-dibromobenzene

Downstream raw materials:

3-(1H-Indol-4-yl)-5-(pyridin-3-ylamino)phenol