2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester

Base Information

• Chemical Name: 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester
• CAS No.: 163688-11-7
• Molecular Formula: C21H23NO3
• Molecular Weight: 337.419
• DSSTox Substance ID: DTXSID201180348
• Mol file: 163688-11-7.mol

Synonyms:SCHEMBL7965041;YDMCETOGPMPTIT-UHFFFAOYSA-N;DTXSID201180348;Methyl 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetate;2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester;163688-11-7

Chemical Property of 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 337.16779360
• Heavy Atom Count: 25
• Complexity: 435

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1=C(C2=C(N1CC3=CC=CC=C3)C=CC(=C2)OC)CC(=O)OC

Technology Process of 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester

There total 5 articles about 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl 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: 44.0%

benzyl chloride (100-44-7) + 2-ethyl-5-methoxyindole-3-acetic acid methyl ester (41800-12-8) → 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester (163688-11-7)

Guidance literature:

In ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

N-(tert-butoxycarbonyl)-4-methoxy-2-methylaniline (129822-42-0) → 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester (163688-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) s-BuLi / 1.) cyclohexane, THF, -40 deg C, 0.25 h, 2.) cyclohexane, THF, from -40 deg C to RT, 2 h

2: 58 percent / CF₃COOH / CH₂Cl₂ / 72 h

3: 1.) n-BuLi, 2.) ZnCl₂

4: 1.) t-BuOK / 1.) DMF, 0.25 min, 2.) DMF, 72 h

With n-butyllithium; potassium tert-butylate; sec.-butyllithium; trifluoroacetic acid; zinc(II) chloride; In dichloromethane;

DOI:10.1021/jm960485v

Reference yield:

1-[2-(tert-butoxycarbonylamino)-5-methoxyphenyl]-2-butanone (163688-09-3) → 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester (163688-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / CF₃COOH / CH₂Cl₂ / 72 h

2: 1.) n-BuLi, 2.) ZnCl₂

3: 1.) t-BuOK / 1.) DMF, 0.25 min, 2.) DMF, 72 h

With n-butyllithium; potassium tert-butylate; trifluoroacetic acid; zinc(II) chloride; In dichloromethane;

DOI:10.1021/jm960485v

upstream raw materials:

benzyl chloride

2-ethyl-5-methoxyindole-3-acetic acid methyl ester

N-(tert-butoxycarbonyl)-4-methoxy-2-methylaniline

1-[2-(tert-butoxycarbonylamino)-5-methoxyphenyl]-2-butanone

Downstream raw materials:

3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole

2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide