METHYL 3-CYCLOHEXYL-2-(2-HYDROXYPHENYL)-1H-INDOLE-6-CARBOXYLATE

Base Information

• Chemical Name: METHYL 3-CYCLOHEXYL-2-(2-HYDROXYPHENYL)-1H-INDOLE-6-CARBOXYLATE
• CAS No.: 863578-50-1
• Molecular Formula: C22H23NO3
• Molecular Weight: 349.43
• Hs Code.: 2933990090
• Mol file: 863578-50-1.mol

Synonyms:METHYL 3-CYCLOHEXYL-2-(2-HYDROXYPHENYL)-1H-INDOLE-6-CARBOXYLATE

Chemical Property of METHYL 3-CYCLOHEXYL-2-(2-HYDROXYPHENYL)-1H-INDOLE-6-CARBOXYLATE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 547.668°C at 760 mmHg
• Flash Point: 285.019°C
• PSA: 62.32000
• Density: 1.227g/cm³
• LogP: 5.37480
• Storage Temp.: 2-8°C

Purity/Quality:

99.0% ^*data from raw suppliers

Methyl3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL 3-CYCLOHEXYL-2-(2-HYDROXYPHENYL)-1H-INDOLE-6-CARBOXYLATE

There total 12 articles about METHYL 3-CYCLOHEXYL-2-(2-HYDROXYPHENYL)-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: 92.0%

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4) → 3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester (863578-50-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride; In ethanol; toluene;

DOI:10.1016/j.bmcl.2011.03.067

Reference yield: 88.0%

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8) + 2-hydroxyphenyl boronic acid (89466-08-0) → 3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester (863578-50-1)

Guidance literature:

With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; for 7h; Heating;

DOI:10.1021/jm0610245

Reference yield: 74.0%

4-[1-cyclohexyl-2-(2-hydroxy-phenyl)-2-oxo-ethyl]-3-nitrobenzoic acid methyl ester (1414926-67-2) → 3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester (863578-50-1)

Guidance literature:

With palladium on carbon; acetic acid; In tetrahydrofuran; at 60 ℃; under 1725.17 Torr; Large scale;

DOI:10.1021/op300303p

upstream raw materials:

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

2-hydroxyphenyl boronic acid

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

2-cyclohexyl-1-(2-hydroxyphenyl)ethan-1-one

Downstream raw materials:

3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester

C₇H₈O₃S*C₂₉H₃₇N₃O₃

methyl (7R)-14-cyclohexyl-7-{[2-(1,3-dioxo-1,3dihydro-2H-isoindol-2-yl)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

methyl (7R)-7-amino-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate hydrochloride

Refernces

• 1、 Narjes, Frank,Crescenzi, Benedetta,Ferrara, Marco,Habermann, J?rg,Colarusso, Stefania,Del Rosario Rico Ferreira, Maria,Stansfield, Ian,MacKay, Angela Claire,Conte, Immacolata,Ercolani, Caterina,Zaramella, Simone,Palumbi, Maria-Cecilia,Meuleman, Philip,Leroux-Roels, Geert,Giuliano, Claudio,Fiore, Fabrizio,Di Marco, Stefania,Baiocco, Paola,Koch, Uwe,Migliaccio, Giovanni,Altamura, Sergio,Laufer, Ralph,De Francesco, Raffaele,Rowley, Michael. "Discovery of (7 R)-14-Cyclohexyl-7-{[2-(dimethylamino)ethyl](methyl) amino}-7,8-dihydro-6 H -indolo[1,2- e ][1,5]benzoxazocine-11-carboxylic Acid (MK-3281), a potent and orally bioavailable finger-loop inhibitor of the hepatitis C virus NS5B polymerase". supporting information; experimental part. p. 289 - 301. Retrieved 2011/03/22.
• 2、 -. "PENTACYCLIC INDOLE DERIVATIVES AS ANTIVIRAL AGENTS". Page/Page column 27. . Retrieved 2008/06/13.