2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide

Base Information

• Chemical Name: 2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide
• CAS No.: 164084-29-1
• Molecular Formula: C20H22N2O2
• Molecular Weight: 322.407
• DSSTox Substance ID: DTXSID70442574
• Wikidata: Q82259921
• Pharos Ligand ID: TCK6ZDTP5RM1
• ChEMBL ID: CHEMBL358458
• Mol file: 164084-29-1.mol

Synonyms:CHEMBL358458;164084-29-1;2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide;SCHEMBL7952979;DTXSID70442574;AYTGRJDCUGRVSB-UHFFFAOYSA-N;2-(1-BENZYL-2-ETHYL-5-METHOXYINDOL-3-YL)ACETAMIDE;BDBM50055785;2-(1-benzyl-2-ethyl-5-methoxy-1h-indol-3-yl) acetamide;2-(1-Benzyl-2-ethyl-5-methoxy-1H-indol-3-yl)-acetamide

Chemical Property of 2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 322.168127949
• Heavy Atom Count: 24
• Complexity: 422

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide

There total 16 articles about 2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide 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: 85.0%

3-(cyanomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole (184705-14-4) → 3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole (164084-29-1)

Guidance literature:

With potassium hydroxide; In tert-butyl alcohol; for 1h; Heating;

DOI:10.1021/jo9614452

Reference yield: 21.0%

2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide (163734-44-9) → 3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole (164084-29-1)

Guidance literature:

With nickel; In ethanol; for 2h; Heating;

DOI:10.1021/jm960485v

Reference yield:

methyl propanoyl acetate (30414-53-0) → 3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole (164084-29-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 95.7 percent / p-toluenesulfonic acid monohydrate / toluene / 3 h / Heating

2: 1.68 g / nitromethane / 48 h / 20 °C

3: 60.6 percent / tetrabutylammonium bromide; aq. NaOH / 0.5 h / Heating

4: 66.4 percent / LiAlH₄ / tetrahydrofuran / 17 h / 20 °C

5: 71.3 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

6: 66.2 percent / KOH / 2-methyl-propan-2-ol / 1 h / Heating

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; tetrabutylammomium bromide; toluene-4-sulfonic acid; In tetrahydrofuran; nitromethane; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0968-0896(00)00292-3

upstream raw materials:

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

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

methyl propanoyl acetate

benzylamine

Downstream raw materials:

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

dimethyl [3-[[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-indol-5-yl]oxy]propyl]phosphonate

ethyl [4-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-indol-5-yl]oxy]butanoate

[3-[[4-allyl-3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester