Methyl 1-benzylindole-3-carboxylate

Base Information

• Chemical Name: Methyl 1-benzylindole-3-carboxylate
• CAS No.: 155134-26-2
• Molecular Formula: C17H15NO2
• Molecular Weight: 265.312
• DSSTox Substance ID: DTXSID20359209
• Nikkaji Number: J579.497H
• Wikidata: Q82140297
• ChEMBL ID: CHEMBL4638829
• Mol file: 155134-26-2.mol

Synonyms:Methyl 1-benzylindole-3-carboxylate;155134-26-2;Methyl 1-benzyl-1H-indole-3-carboxylate;1H-Indole-3-carboxylic acid, 1-(phenylmethyl)-, methyl ester;SCHEMBL2430574;CHEMBL4638829;DTXSID20359209;IDQMIKZRJYUQAP-UHFFFAOYSA-N

Chemical Property of Methyl 1-benzylindole-3-carboxylate

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 265.110278721
• Heavy Atom Count: 20
• Complexity: 338

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CN(C2=CC=CC=C21)CC3=CC=CC=C3

Technology Process of Methyl 1-benzylindole-3-carboxylate

There total 12 articles about Methyl 1-benzylindole-3-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: 96.0%

3-methoxycarbonylindole (942-24-5) + benzyl bromide (100-39-0) → 1-Benzyl-1H-indole-3-carboxylic acid methyl ester (155134-26-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

Reference yield: 92.0%

methyl α-formyl(o-bromophenyl)acetate (122394-37-0) + benzylamine (100-46-9) → 1-Benzyl-1H-indole-3-carboxylic acid methyl ester (155134-26-2)

Guidance literature:

methyl α-formyl(o-bromophenyl)acetate; benzylamine; In methanol; at 20 ℃; for 6h;

With potassium phosphate; copper(l) iodide; ethylene glycol; In N,N-dimethyl-formamide; at 75 ℃; for 4h; Further stages.;

DOI:10.1021/jo800630v

Reference yield: 84.0%

methyl 3-(benzylamino)-2-(2-bromophenyl)acrylate (1265902-10-0) → 1-Benzyl-1H-indole-3-carboxylic acid methyl ester (155134-26-2)

Guidance literature:

With methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II); sodium methylate; ruphos; In 1,4-dioxane; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol5018118

upstream raw materials:

iodoacetonitrile

(E)-3-Phenylamino-pent-2-enedioic acid dimethyl ester

N-benzyl-N-phenylhydroxylamine

propynoic acid methyl ester

Downstream raw materials:

methyl 1-benzyl-2-iodoindole-3(1H)-carboxylate

1-benzyl-2-iodoindole-3(1H)-carboxylic acid

5-benzyl-3-pentylindolo[3,2-c]pyrane-1(5H)-one

5-benzyl-3-(3-hydroxypropan-2-yl)pyrano[4,3-b]indol-1(5H)-one