1-(4-Bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

Base Information

• Chemical Name: 1-(4-Bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole
• CAS No.: 115119-04-5
• Molecular Formula: C21H24BrNO2
• Molecular Weight: 402.331
• DSSTox Substance ID: DTXSID70579697
• Wikidata: Q82470306
• Mol file: 115119-04-5.mol

Synonyms:115119-04-5;SCHEMBL9360609;DTXSID70579697;1-(4-Bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

Chemical Property of 1-(4-Bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

Chemical Property:

• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 401.09904
• Heavy Atom Count: 25
• Complexity: 399

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N(C2=C1C=C(C=C2)OC)CCCCBr)C3=CC=C(C=C3)OC

Technology Process of 1-(4-Bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

There total 2 articles about 1-(4-Bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole 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: 47.0%

1,4-dibromo-butane (110-52-1) + 5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole (91444-18-7) → 1-(4-bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole (115119-04-5)

Guidance literature:

5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.25h;

1,4-dibromo-butane; In tetrahydrofuran; mineral oil; for 2h; Reflux;

DOI:10.1016/j.bmc.2016.06.050

Reference yield:

4-Methoxypropiophenone (121-97-1) → 1-(4-bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole (115119-04-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / ethanol / 6 h / 80 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

2.2: 2 h / Reflux

With hydrogenchloride; sodium hydride; In tetrahydrofuran; ethanol; mineral oil;

DOI:10.1016/j.bmc.2016.06.050

Reference yield: 84.0%

1-(4-bromobutyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole (115119-04-5) + potassium phtalimide (1074-82-4) → 2-{4-[5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-indol-1-yl]-butyl}-isoindole-1,3-dione (132751-72-5)

Guidance literature:

In N,N-dimethyl-formamide; for 2h; Heating;

DOI:10.1021/jm00111a033

upstream raw materials:

1,4-dibromo-butane

5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

4-Methoxypropiophenone

Downstream raw materials:

5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-1-(4-pyrrolidin-1-yl-butyl)-1H-indole

2-{4-[5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-indol-1-yl]-butyl}-isoindole-1,3-dione

1-[4-(2-Amino-ethylamino)-butyl]-2-(4-hydroxy-phenyl)-3-methyl-1H-indol-5-ol

{4-[5-Methoxy-2-(4-methoxy-phenyl)-3-methyl-indol-1-yl]-butyl}-[1-pyridin-2-yl-meth-(E)-ylidene]-amine