1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline

Base Information

• Chemical Name: 1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline
• CAS No.: 1398566-83-0
• Molecular Formula: C₂₆H₁₉NO₂S
• Molecular Weight: 409.508
• Mol file: 1398566-83-0.mol

Synonyms:1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline

Chemical Property of 1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline

There total 2 articles about 1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline 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: 73.0%

3-ethynylthiophene (67237-53-0) + 4-iodo-1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline (1256286-01-7) → 1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline (1398566-83-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; diisopropylamine; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

DOI:10.1021/jo3015374

Reference yield:

2-(2-(p-tolyl)ethynyl)quinoline-3-carbaldehyde (1159765-59-9) → 1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline (1398566-83-0)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine; potassium carbonate / dichloromethane / 25 °C

2: bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; iodine; potassium carbonate; diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/jo3015374

Reference yield: 86.0%

1-methoxy-4-(thiophen-3-ylethynyl)-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline (1398566-83-0) → 3-(4-methylbenzoyl)-1-(thiophen-3-yl)pyrrolo[1,2-a]quinoline-4-carbaldehyde (1398567-00-4)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 25 ℃;

DOI:10.1021/jo3015374

upstream raw materials:

3-ethynylthiophene

4-iodo-1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline

2-(2-(p-tolyl)ethynyl)quinoline-3-carbaldehyde

Downstream raw materials:

3-(4-methylbenzoyl)-1-(thiophen-3-yl)pyrrolo[1,2-a]quinoline-4-carbaldehyde