N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide

Base Information

• Chemical Name: N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide
• CAS No.: 1610611-06-7
• Molecular Formula: C₂₅H₂₂N₆O₂
• Molecular Weight: 438.489
• Mol file: 1610611-06-7.mol

Synonyms:N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide

Chemical Property of N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide

There total 10 articles about N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide 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: 61.0%

[4-(methylcarbamoyl)phenyl]boronic acid + 3-bromo-N-(5-cyanopyridin-2-yl)-N-isopropylpyrazolo[1,5-a]pyridine-5-carboxamide (1610612-26-4) → N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide (1610611-06-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydrogencarbonate; XPhos; In water; acetonitrile; at 100 ℃; for 2.5h; Inert atmosphere;

Reference yield:

2-bromo-5-cyanopyridine (139585-70-9) → N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide (1610611-06-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 16 h / 80 °C / Sealed tube

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C

3: sodium hydrogencarbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; XPhos / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; XPhos; In dichloromethane; water; acetonitrile; 3: |Suzuki Coupling;

Reference yield:

3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid (876379-79-2) → N-(5-cyanopyridin-2-yl)-N-isopropyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide (1610611-06-7)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C

3: sodium hydrogencarbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; XPhos / acetonitrile; water / 2.5 h / 100 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; oxalyl dichloride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; XPhos; In dichloromethane; water; acetonitrile; 3: |Suzuki Coupling;

upstream raw materials:

3-bromo-N-(5-cyanopyridin-2-yl)-N-isopropylpyrazolo[1,5-a]pyridine-5-carboxamide

2-bromo-5-cyanopyridine

3-bromopyrazolo[1,5-a]pyridine-5-carboxylic acid

C₈H₄BrClN₂O