Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Base Information

• Chemical Name: Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate
• CAS No.: 494799-19-8
• Molecular Formula: C16H18 Br N O2
• Molecular Weight: 336.228
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90457766
• Wikidata: Q82280750
• Mol file: 494799-19-8.mol

Synonyms:494799-19-8;Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate;METHYL 2-BROMO-3-CYCLOHEXYL-6-INDOLECARBOXYLATE;Methyl 2-bromo-3-cyclohexyl1H-indole-6-carboxylate;2-Bromo-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester;SCHEMBL50237;2-Bromo-3-cyclohexylindole-6-carboxylic acid methyl ester;DTXSID90457766;TQP0845;QOQJFUQDXVNLMK-UHFFFAOYSA-N;AKOS022178218;SB15023;CS-0092014;FT-0671569;A855081;methyl 2-bromo-3-cyclohexyl-6-indole carboxylate;methyl-2-bromo-3-cyclohexyl-6-indole carboxylate;methyl 2-bromo-3-cyclohexyl-1H-indole-6carboxylate;Methyl2-bromo-3-cyclohexyl-1H-indole-6-carboxylate;Methyl-2-bromo-3-cyclohexyl-1H-indole-6-carboxylate;2-bromo-3-cyclohexyl indole-6-carboxylic acid methyl ester

Chemical Property of Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

Chemical Property:

• Vapor Pressure: 1.42E-08mmHg at 25°C
• Boiling Point: 458oC at 760 mmHg
• Flash Point: 230.8oC
• PSA: 42.09000
• Density: 1.417g/cm3
• LogP: 4.76470
• Storage Temp.: 2-8°C
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 335.05209
• Heavy Atom Count: 20
• Complexity: 356

Purity/Quality:

99.0% ^*data from raw suppliers

Methyl2-Bromo-3-cyclohexyl-6-indolecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)C(=C(N2)Br)C3CCCCC3
• Uses: Methyl 2-Bromo-3-cyclohexyl-6-indolecarboxylate is an indole derivatives as antiviral agents and their use in the treatment of hepatitis C virus infection.

Technology Process of Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

There total 10 articles about Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate 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: 86.0%

methyl 3-cyclohexyl-1H-indole-6-carboxylate (494799-18-7) → methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8)

Guidance literature:

With pyridinium hydrobromide perbromide; In tetrahydrofuran; chloroform; at 0 - 20 ℃; for 2h;

Reference yield: 85.0%

methyl 3-cyclohexyl-1H-indole-6-carboxylate (494799-18-7) + pyridinium perbromide hydrobromide (859064-49-6) → methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8)

Guidance literature:

In tetrahydrofuran; chloroform; at 0 ℃; for 1.5h;

Reference yield:

3-(cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid (494799-16-5) → methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8)

Guidance literature:

Multi-step reaction with 3 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

With pyridine tribromide; hydrogen; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.07.074

upstream raw materials:

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

Indole-6-carboxylic acid

Downstream raw materials:

methyl 3-cyclohexyl-2-vinyl-1H-indole-6-carboxylate

methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate

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

3-cyclohexyl-2-(3-furyl)indole-6-carboxylic acid methyl ester