(Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine

Base Information

• Chemical Name: (Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine
• CAS No.: 1413417-29-4
• Molecular Formula: C₂₂H₂₆INO₄Si
• Molecular Weight: 523.443
• Mol file: 1413417-29-4.mol

Synonyms:(Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine

Chemical Property of (Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine

There total 3 articles about (Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine 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: 80.0%

N-(4-methoxybenzyl)-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide (848061-26-7) → (Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine (1413417-29-4)

Guidance literature:

With iodine; sodium hydrogencarbonate; In acetonitrile; at 20 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/jo301958q

Reference yield:

2-iodo-4,5-dimethoxybenzoic acid (61203-48-3) → (Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine (1413417-29-4)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl dichloride / 0.5 h / 80 °C / Reflux

2: pyridine / tetrahydrofuran / 0 °C

3: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 55 °C / Inert atmosphere

4: iodine; sodium hydrogencarbonate / acetonitrile / 1 h / 20 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; iodine; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; acetonitrile; 3: |Sonogashira Cross-Coupling;

DOI:10.1021/jo301958q

Reference yield:

4,5-dimethoxy-2-iodobenzoyl chloride (113258-92-7) → (Z)-N-((3E)-3-(iodo(trimethylsilyl)methylene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine (1413417-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / tetrahydrofuran / 0 °C

2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 55 °C / Inert atmosphere

3: iodine; sodium hydrogencarbonate / acetonitrile / 1 h / 20 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; iodine; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; acetonitrile; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/jo301958q

upstream raw materials:

N-(4-methoxybenzyl)-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide

2-iodo-4,5-dimethoxybenzoic acid

4,5-dimethoxy-2-iodobenzoyl chloride

Downstream raw materials:

(Z)-N-((3E)-3-(2-bromobenzylidene)-5,6-dimethoxyisobenzofuran-1(3H)-ylidene)-1-(4-methoxyphenyl)methanamine

C₁₉H₁₈INO₄