3-Cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid

Base Information

• Chemical Name: 3-Cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid
• CAS No.: 494799-15-4
• Molecular Formula: C21H21NO2
• Molecular Weight: 319.403
• ChEMBL ID: CHEMBL368884
• DSSTox Substance ID: DTXSID00414981
• Wikidata: Q82224091
• Mol file: 494799-15-4.mol

Synonyms:3-Cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid;494799-15-4;CHEMBL368884;1H-Indole-6-carboxylic acid, 3-cyclohexyl-2-phenyl-;SCHEMBL1173816;DTXSID00414981;XQDXAKPWDOATIZ-UHFFFAOYSA-N;BDBM50162094

Chemical Property of 3-Cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid

Chemical Property:

• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 319.157228913
• Heavy Atom Count: 24
• Complexity: 439

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C2=C(NC3=C2C=CC(=C3)C(=O)O)C4=CC=CC=C4

Technology Process of 3-Cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid

There total 9 articles about 3-Cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid 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: 100.0%

3-cyclohexyl-2-phenylindole-6-carboxylic acid methyl ester (494799-14-3) → 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid (494799-15-4)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃;

Reference yield:

3-(cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid (494799-16-5) → 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid (494799-15-4)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd(OH)2/C / methanol; tetrahydrofuran / 24 h / 20 °C / 2844.31 Torr

2: 21.90 g / K₂CO₃ / dimethylformamide / 20 °C

3: 71 percent / pyridine tribromide / tetrahydrofuran; CHCl₃ / 2.5 h / 0 - 20 °C

4: 88 percent / LiCl; Na₂CO₃; Pd(PPh₃)4 / toluene; ethanol; H₂O / 80 °C

5: NaOH

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyridine tribromide; hydrogen; sodium carbonate; potassium carbonate; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene; 4: Suzuki cross-coupling;

DOI:10.1016/j.bmcl.2006.07.074

Reference yield:

indole-6-carboxylic acid methyl ester (50820-65-0) → 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid (494799-15-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaOMe / methanol / 12 h / Heating

1.2: 99 percent / aq. NaOH / methanol / 4 h / Heating

2.1: H₂ / Pd(OH)2/C / tetrahydrofuran; methanol / 24 h

3.1: 57.6 g / K₂CO₃ / dimethylformamide / 4 h / 20 °C

4.1: 65 percent / NBS / CCl₄ / 12 h / 25 °C

5.1: 65 percent / aq. Na₂CO₃; Pd(PPh₃)4 / ethanol; 1,2-dimethoxy-ethane / 6 h / 80 °C

6.1: 58 percent / aq. LiOH / tetrahydrofuran / 8 h / 70 °C

With lithium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; sodium methylate; sodium carbonate; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm049122i

upstream raw materials:

3-cyclohexyl-2-phenylindole-6-carboxylic acid methyl ester

methyl 3-cyclohexyl-1H-indole-6-carboxylate

3-cyclohexyl-1-methyl-1H-indole-6-carboxylic acid

3-(cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid