7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine

Base Information

• Chemical Name: 7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine
• CAS No.: 475171-53-0
• Molecular Formula: C₂₄H₂₈ClN₃O
• Molecular Weight: 409.959
• Mol file: 475171-53-0.mol

Synonyms:

Chemical Property of 7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine

There total 7 articles about 7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine 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:

[7-(2-chloro-4-methoxyphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine (475174-90-4) + 2-cyclopropylacetaldehyde (56105-19-2) → 7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine (475171-53-0)

Guidance literature:

With sodium tetrahydroborate; sulfuric acid; In tetrahydrofuran; water; at 0 ℃; for 0.333333h;

DOI:10.1021/jm300259r

Reference yield:

2-bromo-pyridine (109-04-6) → 7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine (475171-53-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / diethylamine / 10 h / 20 °C

2.1: dichloromethane / 1 h / 0 °C / Cooling with ice

3.1: sodium methylate / methanol / 0.5 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

4.2: 0.17 h / -78 °C / Inert atmosphere

5.1: nitronium tetrafluoborate / acetonitrile / 0.17 h / 0 °C / Cooling with ice

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; barium hydroxide octahydrate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere

7.1: acetic acid; zinc / ethanol; water / 0.5 h / 20 - 60 °C

8.1: sodium tetrahydroborate; sulfuric acid / tetrahydrofuran; water / 0.33 h / 0 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; nitronium tetrafluoborate; barium hydroxide octahydrate; sulfuric acid; sodium methylate; acetic acid; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; diethylamine; acetonitrile; 6.1: Suzuki coupling;

DOI:10.1021/jm300259r

Reference yield:

N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate (475174-67-5) → 7-(2-chloro-4-methoxyphenyl)-N,N-bis(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine (475171-53-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium methylate / methanol / 0.5 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

3.1: nitronium tetrafluoborate / acetonitrile / 0.17 h / 0 °C / Cooling with ice

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; barium hydroxide octahydrate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere

5.1: acetic acid; zinc / ethanol; water / 0.5 h / 20 - 60 °C

6.1: sodium tetrahydroborate; sulfuric acid / tetrahydrofuran; water / 0.33 h / 0 °C

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; nitronium tetrafluoborate; barium hydroxide octahydrate; sulfuric acid; sodium methylate; acetic acid; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; water; acetonitrile; 4.1: Suzuki coupling;

DOI:10.1021/jm300259r

upstream raw materials:

2-bromo-pyridine

2-ethylpyrazolo[1,5-a]pyridine

N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate

[7-(2-chloro-4-methoxyphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine