3-(4-Fluorophenoxymethyl)-1,2-dimethyl-5-methoxy-1H-indole-4,7-dione

Base Information

• Chemical Name: 3-(4-Fluorophenoxymethyl)-1,2-dimethyl-5-methoxy-1H-indole-4,7-dione
• CAS No.: 192820-80-7
• Molecular Formula: C₁₈H₁₆FNO₄
• Molecular Weight: 329.328
• DSSTox Substance ID: DTXSID701154916
• Nikkaji Number: J1.013.439K
• ChEMBL ID: CHEMBL330583
• Mol file: 192820-80-7.mol

Synonyms:CHEMBL330583;DTXSID701154916;3-(4-Fluorophenoxymethyl)-1,2-dimethyl-5-methoxy-1H-indole-4,7-dione;3-[(4-Fluorophenoxy)methyl]-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione;192820-80-7

Chemical Property of 3-(4-Fluorophenoxymethyl)-1,2-dimethyl-5-methoxy-1H-indole-4,7-dione

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 329.10633615
• Heavy Atom Count: 24
• Complexity: 541

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(N1C)C(=O)C=C(C2=O)OC)COC3=CC=C(C=C3)F

Technology Process of 3-(4-Fluorophenoxymethyl)-1,2-dimethyl-5-methoxy-1H-indole-4,7-dione

There total 5 articles about 3-(4-Fluorophenoxymethyl)-1,2-dimethyl-5-methoxy-1H-indole-4,7-dione 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:

3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione (161518-24-7) → 3-(4-Fluoro-phenoxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione (192820-80-7)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 0.5 h / Ambient temperature

2: NaH / dimethylformamide / 3 h / Ambient temperature

With thionyl chloride; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jm970744w

Reference yield:

5-Methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester (205177-88-4) → 3-(4-Fluoro-phenoxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione (192820-80-7)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. sodium dithionite / CHCl₃; ethanol

2: DIBAL-H / CH₂Cl₂ / 2 h / -30 °C

3: SOCl₂ / 0.5 h / Ambient temperature

4: NaH / dimethylformamide / 3 h / Ambient temperature

With thionyl chloride; sodium dithionite; sodium hydride; diisobutylaluminium hydride; In ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm970744w

Reference yield:

ethyl 4,7-dihydroxy-5-methoxy-1,2-dimethylindole-3-carboxylate → 3-(4-Fluoro-phenoxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione (192820-80-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAL-H / CH₂Cl₂ / 2 h / -30 °C

2: SOCl₂ / 0.5 h / Ambient temperature

3: NaH / dimethylformamide / 3 h / Ambient temperature

With thionyl chloride; sodium hydride; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970744w

upstream raw materials:

3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione

5-Methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester

Downstream raw materials:

acetone

Refernces