[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Base Information

Chemical Name:[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester
CAS No.:405939-38-0
Molecular Formula:C₂₉H₃₉ClN₄O₄Si
Molecular Weight:571.192
Hs Code.:

[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid <i>tert</i>-butyl ester

Synonyms:[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester

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Chemical Property of [3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester

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Technology Process of [3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester

There total 6 articles about [3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic 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:

: 20986-40-7
ethyl 5-bromo-3-pyridinecarboxylate

: 405939-38-0
[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: bis(tributyltin); tri-o-tolylphosphine; triethylamine / palladium acetate / acetonitrile / 22 h / 95 - 100 °C

1.2: 3.56 g / dichloro-bis(triphenylphosphine)palladium; LiCl / toluene / 23 h / 100 °C

2.1: 27 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾*CHCl₃; 1,1'-bis(diphenylphosphino)ferrocene; Cs₂CO₃ / dioxane / 39 h / 110 °C

3.1: 85 percent / aq. NaOH / methanol / 18 h / 20 °C

4.1: 40 percent / diphenylphosphoryl azide; triethylamine / toluene / 19.5 h / 70 - 100 °C

5.1: Cs₂CO₃ / dimethylformamide / 72 h / 70 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; diphenylphosphoranyl azide; bis(tri-n-butyltin); caesium carbonate; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; acetonitrile; 1.2: Stille coupling / 4.1: Curtius rearrangement;
DOI:10.1021/jm058205b

Reference yield:

: 405939-37-9
{5-[6-(3-chlorophenoxy)pyrazin-2-yl]pyridin-3-yl}carbamic acid tert-butyl ester

: 89031-84-5
3-(tert-butyldimethylsilyloxy)propyl bromide

: 405939-38-0
[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 72h;
DOI:10.1021/jm058205b

Reference yield:

: 405938-99-0
5-(6-chloropyrazine-2-yl)nicotinic acid ethyl ester

: 405939-38-0
[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-{5-[6-(3-chloro-phenoxy)-pyrazin-2-yl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 27 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾*CHCl₃; 1,1'-bis(diphenylphosphino)ferrocene; Cs₂CO₃ / dioxane / 39 h / 110 °C

2: 85 percent / aq. NaOH / methanol / 18 h / 20 °C

3: 40 percent / diphenylphosphoryl azide; triethylamine / toluene / 19.5 h / 70 - 100 °C

4: Cs₂CO₃ / dimethylformamide / 72 h / 70 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; diphenylphosphoranyl azide; caesium carbonate; triethylamine; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; 3: Curtius rearrangement;
DOI:10.1021/jm058205b