5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one

Base Information

Chemical Name:5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one
CAS No.:860032-33-3
Molecular Formula:C₄₂H₅₄N₄O₄Si
Molecular Weight:707.001
Hs Code.:

Synonyms:5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one

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Chemical Property of 5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one

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Technology Process of 5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one

There total 7 articles about 5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one 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: 65.0%

: 530084-80-1
8-benzyloxy-5-[(R)-2-[2-(4-bromo-phenyl)-ethylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-quinolin-2-one hydrochloride

: {4-[(2-amino-2-methylpropyl)oxy]phenyl}amine dihydrochloride

: 860032-33-3
5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one

Guidance literature:: 8-benzyloxy-5-[(R)-2-[2-(4-bromo-phenyl)-ethylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-quinolin-2-one hydrochloride; {4-[(2-amino-2-methylpropyl)oxy]phenyl}amine dihydrochloride; With sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 84 - 90 ℃; for 4h;

With hydrogenchloride; In 1,4-dioxane; methanol; acetic acid methyl ester; water; at 47 - 53 ℃; for 17h;

With sodium hydroxide; In 1,4-dioxane; methanol; acetic acid methyl ester; water; at 17 - 23 ℃; Product distribution / selectivity;

Reference yield:

: 530084-80-1
8-benzyloxy-5-[(R)-2-[2-(4-bromo-phenyl)-ethylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-quinolin-2-one hydrochloride

: 900523-76-4
4-(2-amino-2-methyl-propoxy)-phenylamine hydrochloride

: 860032-33-3
5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one

Guidance literature:: 8-benzyloxy-5-[(R)-2-[2-(4-bromo-phenyl)-ethylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-quinolin-2-one hydrochloride; 4-(2-amino-2-methyl-propoxy)-phenylamine hydrochloride; With sodium t-butanolate; In toluene; at 90 ℃;

tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 90 ℃; for 3h;

Reference yield:

: 530084-74-3
(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one

: 860032-33-3
5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-benzyloxy-1H-quinolin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: dimethyl sulfoxide

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In dimethyl sulfoxide; toluene; 2: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmcl.2014.04.095