Benzyl 1H-indole-4-carboxylate

Base Information

• Chemical Name: Benzyl 1H-indole-4-carboxylate
• CAS No.: 84401-11-6
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.285
• DSSTox Substance ID: DTXSID10510842
• Wikidata: Q82369368
• Mol file: 84401-11-6.mol

Synonyms:Benzyl 1H-indole-4-carboxylate;84401-11-6;benzyl indole-4-carboxylate;SCHEMBL7425563;DTXSID10510842;UPIHDKSHKSBWEM-UHFFFAOYSA-N

Chemical Property of Benzyl 1H-indole-4-carboxylate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 251.094628657
• Heavy Atom Count: 19
• Complexity: 312

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C2=C3C=CNC3=CC=C2

Technology Process of Benzyl 1H-indole-4-carboxylate

There total 2 articles about Benzyl 1H-indole-4-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: 89.0%

1H-indole-4-carboxylic acid (2124-55-2) + O-benzyl-N,N'-dicyclohexylisourea (6738-17-6) → benzyl indole-4-carboxylate (84401-11-6)

Guidance literature:

In N,N-dimethyl-formamide; at 65 - 70 ℃; for 3h;

Reference yield: 83.4%

1H-indole-4-carboxylic acid (2124-55-2) + benzyl bromide (100-39-0) → benzyl indole-4-carboxylate (84401-11-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Time;

Reference yield: 97.0%

benzyl indole-4-carboxylate (84401-11-6) + benzoyl chloride (98-88-4) → benzyl 1-benzoylindole-4-carboxylate (84401-12-7)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; at 15 ℃; for 0.5h;

upstream raw materials:

1H-indole-4-carboxylic acid

O-benzyl-N,N'-dicyclohexylisourea

benzyl bromide

Downstream raw materials:

benzyl 1-benzoylindole-4-carboxylate

3-(4-Chloromethyl-benzoyl)-1-dimethylcarbamoyl-1H-indole-4-carboxylic acid benzyl ester

1-N,N-dimethylcarbamoyl-4-benzyloxycarbonyl-3-{4-[(1H-2-methylimidazo[4.5-c]pyrid-1-yl)methyl]benzoyl}indole

2-(1H-indol-4-yl)acetic acid

Refernces

• 1、 Curtin, Michael L.,Davidsen, Steven K.,Heyman, H. Robin,Garland, Robert B.,Sheppard, George S.,Florjancic, Alan S.,Xu, Lianhong,Carrera Jr., George M.,Steinman, Douglas H.,Trautmann, Jeff A.,Albert, Daniel H.,Magoc, Terrance J.,Tapang, Paul,Rhein, David A.,Conway, Richard G.,Luo, Gongjin,Denissen, Jon F.,Marsh, Kennan C.,Morgan, Douglas W.,Summers, James B.. "Discovery and evaluation of a series of 3-acylindole imidazopyridine platelet-activating factor antagonists". . p. 74 - 95. Retrieved 2007/10/03.