Methyl indolyl-3-glyoxylate

Base Information

• Chemical Name: Methyl indolyl-3-glyoxylate
• CAS No.: 18372-22-0
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• Mol file: 18372-22-0.mol

Synonyms:Indole-3-glyoxylicacid, methyl ester (6CI,7CI,8CI);(1H-Indol-3-yl)(oxo)acetic acid methyl ester;2-(1H-Indol-3-yl)-2-oxoacetic acid methyl ester;Methyl2-(1H-indol-3-yl)-2-oxoacetate;Methyl 2-(3-indolyl)glyoxylate;Methyl2-(indol-3-yl)-2-oxoacetate;Methyl 3-indoleglyoxylate;

Chemical Property of Methyl indolyl-3-glyoxylate

Chemical Property:

• Appearance/Colour: Pale yellow fine powder
• Vapor Pressure: 4.46E-06mmHg at 25°C
• Melting Point: 227-230 °C(lit.)
• Refractive Index: 1.635
• Boiling Point: 383.2 °C at 760 mmHg
• PKA: 14.54±0.30(Predicted)
• Flash Point: 185.6 °C
• PSA: 59.16000
• Density: 1.324 g/cm³
• LogP: 1.52360
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetone, Methanol

Purity/Quality:

98%,99%, ^*data from raw suppliers

MethylIndolyl-3-glyoxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant for preparation of sotrastaurin analogs as protein kinase inhibitors 1 Reactant for synthesis of GSK-3 inhibitors 2 Reactant for Diels-Alder cycloaddition 3 Reactant for preparation of a Janus kinase 3 inhibitor 4 Reactant for synthesis of cephalandole alkaloids 5 Reactant for stereoselective preparation of COX-2 inhibitor as anticancer agent 6 Reactant for synthesis of cycloalkene indole carbazole alkaloids via ring-closing metathesis. Methyl Indolyl-3-glyoxylate (cas# 18372-22-0) is a compound useful in organic synthesis.

Technology Process of Methyl indolyl-3-glyoxylate

There total 18 articles about Methyl indolyl-3-glyoxylate 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-indolylglyoxylic acid (1477-49-2) + diazomethyl-trimethyl-silane (18107-18-1) → 2-(3-indolyl)oxoacetic acid methyl ester (18372-22-0)

Guidance literature:

In methanol; hexane; benzene; at 20 ℃; for 4h;

DOI:10.1021/jo9914723

Reference yield: 99.0%

methyl 3-(2-methoxy-2-oxoacetyl)-1H-indole-1-carboxylate → 2-(3-indolyl)oxoacetic acid methyl ester (18372-22-0)

Guidance literature:

With tert-butylamine; In methanol; for 4h; Heating;

DOI:10.1016/j.tetlet.2006.11.024

Reference yield: 90.0%

indole (120-72-9) + oxalyl dichloride (79-37-8) + sodium methylate (124-41-4) → 2-(3-indolyl)oxoacetic acid methyl ester (18372-22-0)

Guidance literature:

indole; oxalyl dichloride; In diethyl ether; at 0 ℃; for 1h; Inert atmosphere;

sodium methylate; With methanol; In diethyl ether; at -70 - 0 ℃;

DOI:10.1016/j.cclet.2017.08.019

upstream raw materials:

methanol

indolyl-3-glyoxylyl chloride

monomethyl oxalyl chloride

indole

Downstream raw materials:

methyl 2-(1-methyl-1H-indol-3-yl)-2-oxoacetate

indole-3-glyoxylamide

3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione

bisindolylmaleimide I

Refernces

• 1、 Reeve et al.. "-". . p. 1243,1247. Retrieved 1963.
• 2、 Menozzi, Candice,Dalko, Peter I.,Cossy, Janine. "Concise synthesis of the (±)-Nb-desmethyl-meso- chimonanthine". . p. 4638 - 4640. Retrieved 2006.
• 3、 Hu, Yuanyuan,Gao, Anhui,Liao, Honghui,Zhang, Mengmeng,Xu, Gaoya,Gao, Lixin,Xu, Lei,Zhou, Yubo,Gao, Jianrong,Ye, Qing,Li, Jia. "3-(7-Azaindolyl)-4-indolylmaleimides as a novel class of mutant isocitrate dehydrogenase-1 inhibitors: Design, synthesis, and biological evaluation". . . Retrieved 2018/09/06.