1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: 1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester
• CAS No.: 1427037-69-1
• Molecular Formula: C₂₂H₂₃NO₄
• Molecular Weight: 365.429
• Mol file: 1427037-69-1.mol

Synonyms:1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester

Chemical Property of 1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester

There total 7 articles about 1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester 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-hydroxy-5-methoxy-1-allyl-1H-indole-2-carboxylic acid ethyl ester (1315335-86-4) + benzyl bromide (100-39-0) → 1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester (1427037-69-1) + C22H25NO4

Guidance literature:

With potassium carbonate; In acetone; at 130 ℃; for 1.5h; Overall yield = 88 %; Overall yield = 58.4 mg; Microwave irradiation;

DOI:10.1016/j.tet.2013.01.090

Reference yield:

1-allyl-3,5-dimethoxy-1H-indole-2-carboxylic acid ethyl ester (1427037-67-9) → 1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester (1427037-69-1) + C22H25NO4

Guidance literature:

Multi-step reaction with 2 steps

1: boron tribromide / dichloromethane; hexane / 0.75 h / -30 °C

2: potassium carbonate / acetone / 1.5 h / 130 °C / Microwave irradiation

With boron tribromide; potassium carbonate; In hexane; dichloromethane; acetone;

DOI:10.1016/j.tet.2013.01.090

Reference yield:

5-methoxy-1H-indole-2-carboxylic acid (4382-54-1) → 1-allyl-2-benzyl-5-methoxy-3-oxo-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester (1427037-69-1) + C22H25NO4

Guidance literature:

Multi-step reaction with 7 steps

1: sulfuric acid / 10 h / Reflux

2: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 20 °C

3: toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 8 h / 20 °C

4: diazomethyl-trimethyl-silane / tetrahydrofuran; hexane / 24 h / 20 °C

5: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C

6: boron tribromide / dichloromethane; hexane / 0.75 h / -30 °C

7: potassium carbonate / acetone / 1.5 h / 130 °C / Microwave irradiation

With sulfuric acid; boron tribromide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; diazomethyl-trimethyl-silane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2013.01.090

upstream raw materials:

ethyl 5-methoxy-1H-indole-2-carboxylate

3-hydroxy-5-methoxyindole-2-carboxylic acid ethyl ester

3-formyl-5-methoxy-indole-2-carboxylic acid ethyl ester

3,5-dimethoxy-1H-indole-2-carboxylic acid ethyl ester