tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate
• CAS No.: 1400287-04-8
• Molecular Formula: C₂₄H₂₇N₅O₄
• Molecular Weight: 449.509
• Mol file: 1400287-04-8.mol

Synonyms:

Chemical Property of tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

There total 5 articles about tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate 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:

N-(2-bromo-5-iodopyridin-4-yl)methanesulfonamide (1400286-60-3) → tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (1400287-04-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 1.17 h / 60 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; methanol / 3 h / 40 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

3.2: 0.5 h

4.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 19 h / 80 °C / Microwave irradiation

With sodium hydride; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; mineral oil;

Reference yield:

tert-butyl 4-(6-bromo-1-(methylsulfonyl)-1H-pyrrolo-[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (1400286-61-4) → tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (1400287-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tert-butyl alcohol; tetrahydrofuran / 1 h / 40 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2.2: 0.5 h

3.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 19 h / 80 °C / Microwave irradiation

With sodium hydride; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;

Reference yield:

4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester (121669-70-3) → tert-butyl 4-(6-(3,4-dimethoxyphenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (1400287-04-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisopropylamine / triphenylphosphine; palladium diacetate; copper(l) iodide / N,N-dimethyl-formamide / 1.25 h / 60 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 - 5 °C

3.1: triethylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 1.17 h / 60 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tert-butyl alcohol; tetrahydrofuran / 1 h / 40 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

5.2: 0.5 h

6.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 19 h / 80 °C / Microwave irradiation

With tetrabutyl ammonium fluoride; sodium hydride; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; palladium diacetate; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;

upstream raw materials:

4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester

N-(2-bromo-5-iodopyridin-4-yl)methanesulfonamide

tert-butyl 4-(6-bromo-1-(methylsulfonyl)-1H-pyrrolo-[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

tert-butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate