methyl 6-methyl-1H-indole-2-carboxylate

Base Information

• Chemical Name: methyl 6-methyl-1H-indole-2-carboxylate
• CAS No.: 18377-65-6
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.214
• Hs Code.: 2933990090
• European Community (EC) Number: 820-361-5
• DSSTox Substance ID: DTXSID40405833
• Nikkaji Number: J2.475.475H
• Wikidata: Q82210549
• Mol file: 18377-65-6.mol

Synonyms:methyl 6-methyl-1H-indole-2-carboxylate;18377-65-6;6-methyl-1H-indole-2-carboxylic acid methyl ester;6-Methyl indole-2-carboxylic acid Methylester;6-methylindole-2-carboxylic acid methyl ester;Methyl 6-methylindole-2-carboxylate;SCHEMBL3275257;DTXSID40405833;UYJKPZLQOCBHOS-UHFFFAOYSA-N;HMS1629F03;AMY40744;BBL022464;MFCD06653197;STK504646;AKOS000123961;AS-5789;SB15197;CS-0206012;FT-0732586;EN300-37192;E77281;Z307730432

Chemical Property of methyl 6-methyl-1H-indole-2-carboxylate

Chemical Property:

• Melting Point: 97-98 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Boiling Point: 337.7±22.0 °C(Predicted)
• PKA: 15.33±0.30(Predicted)
• PSA: 42.09000
• Density: 1.212±0.06 g/cm3(Predicted)
• LogP: 2.26290
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

98%min ^*data from raw suppliers

Methyl6-Methyl-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)C=C(N2)C(=O)OC
• Uses: Methyl 6-Methyl-1H-indole-2-carboxylate can be used as MTHFD2 inhibitors.

Technology Process of methyl 6-methyl-1H-indole-2-carboxylate

There total 16 articles about methyl 6-methyl-1H-indole-2-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%

C11H11NO4 → methyl 6-methyl-1H-indole-2-carboxylate (18377-65-6)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); 1,10-Phenanthroline; phenyl formate; triethylamine; In acetonitrile; at 140 ℃; for 3h; Inert atmosphere;

DOI:10.1002/cctc.201701214

Reference yield: 96.0%

methyl (E)-3-(4′-methyl-2′-nitrophenyl)acrylate (99843-45-5) → methyl 6-methyl-1H-indole-2-carboxylate (18377-65-6)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); 1,10-Phenanthroline; phenyl formate; triethylamine; In acetonitrile; at 140 ℃; for 3h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1002/ejoc.202100789

Reference yield: 95.0%

(Z)-methyl 2-azido-3-(p-tolyl)acrylate (102244-84-8) → methyl 6-methyl-1H-indole-2-carboxylate (18377-65-6)

Guidance literature:

In xylene; for 0.333333h; Heating;

DOI:10.1055/s-1985-31149

upstream raw materials:

(Z)-methyl 2-azido-3-(p-tolyl)acrylate

3-dimethylamino-2-m-tolylamino-acrylic acid methyl ester

4-methyl-benzaldehyde

methyl 2-(m-tolylamino)acetate

Refernces

• 1、 Formenti, Dario,Ferretti, Francesco,Ragaini, Fabio. "Synthesis of N-Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates". . p. 148 - 152. Retrieved 2017/12/04.
• 2、 Zhu, Zhiqiang,Yuan, Jiangjun,Zhou, Yirong,Qin, Yang,Xu, Jingshi,Peng, Yiyuan. "Ligand-free copper-catalyzed one-pot synthesis of indole-2-carboxylic esters". supporting information. p. 511 - 514. Retrieved 2014/02/14.