3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin

Base Information

• Chemical Name: 3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin
• CAS No.: 1202395-56-9
• Molecular Formula: C₂₅H₂₀N₂O₃
• Molecular Weight: 396.445
• Mol file: 1202395-56-9.mol

Synonyms:3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin

Chemical Property of 3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin

There total 6 articles about 3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin 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: 75.0%

N-(4'-methoxybenzyl)-4-iodoaniline (1039968-13-2) + 3-amino-4-ethynyl-2H-chromen-2-one (1202395-48-9) → 3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin (1202395-56-9)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1002/adsc.200900287

Reference yield:

4-hydroxy-3-nitrocoumarin (20261-31-8) → 3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin (1202395-56-9)

Guidance literature:

Multi-step reaction with 5 steps

1: trichlorophosphate / N,N-dimethyl-formamide / 20 °C

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

3: iron; acetic acid / dichloromethane; water / 0.5 h / 20 °C

4: potassium fluoride monohydrate / methanol / 0.5 h

5: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium fluoride monohydrate; iron; potassium carbonate; acetic acid; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 2: Sonogashira coupling / 5: Sonogashira coupling;

DOI:10.1002/adsc.200900287

Reference yield:

4-((trimethylsilyl)ethynyl)-3-nitrocoumarin (1202395-43-4) → 3-amino-4-((4-(4-methoxybenzylamino)phenyl)ethynyl)coumarin (1202395-56-9)

Guidance literature:

Multi-step reaction with 3 steps

1: iron; acetic acid / dichloromethane; water / 0.5 h / 20 °C

2: potassium fluoride monohydrate / methanol / 0.5 h

3: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium fluoride monohydrate; iron; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 3: Sonogashira coupling;

DOI:10.1002/adsc.200900287

upstream raw materials:

4-hydroxy-3-nitrocoumarin

N-(4'-methoxybenzyl)-4-iodoaniline

3-amino-4-ethynyl-2H-chromen-2-one

4-((trimethylsilyl)ethynyl)-3-nitrocoumarin

Downstream raw materials:

2-[4-(4-methoxybenzylamino)phenyl]chromeno[3,4-b]pyrrol-4(3H)-one