2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester

Base Information

• Chemical Name: 2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester
• CAS No.: 851962-04-4
• Molecular Formula: C₂₄H₂₄Cl₂N₂O₃S₂
• Molecular Weight: 523.504
• Mol file: 851962-04-4.mol

Synonyms:2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester

Chemical Property of 2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester

There total 7 articles about 2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl 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: 91.0%

tert-butyl 2-(4-hydroxy-3,5-dichlorophenylamino)benzoate (851962-03-3) + 2-(2-(Pyridin-2-yl)disulfanyl)ethanol (111625-28-6) → 2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester (851962-04-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 1h;

DOI:10.1021/ja042929f

Reference yield:

tert-butyl 2-(4-benzyloxy-3,5-dichlorophenylamino)benzoate (851962-02-2) → 2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester (851962-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / H₂ / Pd/C / methanol; ethyl acetate / 16 h

2: 91 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h

With di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; 2: Mitsunobu reaction;

DOI:10.1021/ja042929f

Reference yield:

tert-butyl 2-bromobenzoate (55666-42-7) → 2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid tert-butyl ester (851962-04-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / tris(dibenzylidenoacetone)dipalladium⁽⁰⁾; (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; cesium carbonate / toluene / 24 h / Heating

2: 89 percent / H₂ / Pd/C / methanol; ethyl acetate / 16 h

3: 91 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; di-isopropyl azodicarboxylate; hydrogen; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; 3: Mitsunobu reaction;

DOI:10.1021/ja042929f

upstream raw materials:

tert-butyl 2-(4-hydroxy-3,5-dichlorophenylamino)benzoate

2-(2-(Pyridin-2-yl)disulfanyl)ethanol

tert-butyl 2-(4-benzyloxy-3,5-dichlorophenylamino)benzoate

2,2'-dipyridyldisulphide

Downstream raw materials:

2-{3,5-dichloro-4-[2-(pyridin-2-yldisulfanyl)-ethoxy]-phenylamino}-benzoic acid