tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate
• CAS No.: 1400285-21-3
• Molecular Formula: C₂₃H₂₅N₅O₃
• Molecular Weight: 419.483

Synonyms:tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Chemical Property of tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

There total 7 articles about tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-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:

1-methyl-4-((trimethylsilyl)ethynyl)-1H-pyrazole (1201657-09-1) → tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1400285-21-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / methanol / 2 h / 20 °C

2.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

2.2: 1.75 h / 20 °C

3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 3 h / 50 °C / Inert atmosphere

4.1: triethylamine; dmap / ethyl acetate / 0.42 h / 20 °C

5.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane; N,N-dimethyl acetamide / 2.5 h / 80 °C / Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; potassium tert-butylate; potassium carbonate; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; N,N-dimethyl acetamide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm401395s

Reference yield:

2-bromo-4-aminopyridine (7598-35-8) → tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1400285-21-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic acid; sodium acetate; Iodine monochloride / 3 h / 75 °C

2.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

2.2: 1.75 h / 20 °C

3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 3 h / 50 °C / Inert atmosphere

4.1: triethylamine; dmap / ethyl acetate / 0.42 h / 20 °C

5.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane; N,N-dimethyl acetamide / 2.5 h / 80 °C / Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; potassium tert-butylate; sodium acetate; Iodine monochloride; caesium carbonate; acetic acid; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; N,N-dimethyl acetamide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm401395s

Reference yield:

4-amino-2-bromo-5-iodopyridine (1300750-78-0) → tert-butyl 6-(2-methoxyphenylamino)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1400285-21-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

1.2: 1.75 h / 20 °C

2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 3 h / 50 °C / Inert atmosphere

3.1: triethylamine; dmap / ethyl acetate / 0.42 h / 20 °C

4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane; N,N-dimethyl acetamide / 2.5 h / 80 °C / Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; potassium tert-butylate; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; N,N-dimethyl acetamide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm401395s

upstream raw materials:

1-methyl-4-((trimethylsilyl)ethynyl)-1H-pyrazole

2-bromo-4-aminopyridine

4-amino-2-bromo-5-iodopyridine

4-ethynyl-1-methyl-1-H-pyrazole

Downstream raw materials:

N-(2-methoxyphenyl)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridin-6-amine

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