Methyl 5-methoxy-1H-indole-3-carboxylate

Base Information

• Chemical Name: Methyl 5-methoxy-1H-indole-3-carboxylate
• CAS No.: 172595-68-5
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.21
• Hs Code.: 2933990090
• Mol file: 172595-68-5.mol

Synonyms:5-Methoxyindole-3-carboxylicacid methyl ester;

Chemical Property of Methyl 5-methoxy-1H-indole-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.613
• Boiling Point: 370.062 °C at 760 mmHg
• Flash Point: 177.608 °C
• PSA: 51.32000
• Density: 1.253 g/cm³
• LogP: 1.96310
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

Methyl5-Methoxy-1H-indole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 5-methoxy-1H-indole-3-carboxylate is a useful reactant for the synthesis of tetrahydropyridoindoles via ruthenium-catalyzed decarboxylative C-H alkenylation .

Technology Process of Methyl 5-methoxy-1H-indole-3-carboxylate

There total 8 articles about Methyl 5-methoxy-1H-indole-3-carboxylate 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: 97.0%

methyl 3,3-dimethoxypropionate (7424-91-1) + 4-methoxyphenylhydrazine hydrochloride (19501-58-7) → methyl 5-methoxy-1H-indole-3-carboxylate (172595-68-5)

Guidance literature:

With acetic acid; at 70 ℃; for 4.5h;

Reference yield: 90.0%

methanol (67-56-1) + 5-methoxylindole (1006-94-6) + trifluoroacetyl chloride (76-02-8) → methyl 5-methoxy-1H-indole-3-carboxylate (172595-68-5)

Guidance literature:

5-methoxylindole; trifluoroacetyl chloride; With pyridine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

methanol; With potassium hydroxide; water; Reflux; Inert atmosphere;

DOI:10.1021/ja807026z

Reference yield: 80.0%

C16H19NO4 → methyl 5-methoxy-1H-indole-3-carboxylate (172595-68-5)

Guidance literature:

With manganese(III) triacetate dihydrate; acetic acid; at 85 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2016.03.012

upstream raw materials:

methyl 3,3-dimethoxypropionate

4-methoxyphenylhydrazine hydrochloride

methanol

5-methoxylindole

Downstream raw materials:

5-Methoxyindole-3-carboxylic acid

2-(2-(3,5-bis-(trifluoromethyl)benzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetic acid

Refernces

• 1、 Zaienne, Daniel,Willems, Sabine,Schierle, Simone,Heering, Jan,Merk, Daniel. "Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1". . p. 15126 - 15140. Retrieved 2021/10/25.
• 2、 Abe, Takumi,Yamada, Koji. "Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E". supporting information. p. 6504 - 6507. Retrieved 2016/12/23.