Production Method 1

363591-06-4

942-24-5

Reaction Conditions

1.1 Reagents: tert-Butylamine Solvents: Methanol ;  0.5 h, reflux; reflux → rt

Reference

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

Suarez-Castillo, Oscar R.; Montiel-Ortega, Luis Alberto; Melendez-Rodriguez, Myriam; Sanchez-Zavala, Maricruz, Tetrahedron Letters, 2007, 48(1), 17-20

Production Method 2

771-50-6

942-24-5

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  2 - 3 h, 80 °C

Reference

Microwave-assisted synthesis of new hydrazone compounds with two indole rings with antibacterial activities

Ye, Ying; Suo, You-rui; Yang, Fang; Yang, Yong-jing; Han, Li-juan, Huaxue Shiji, 2015, 37(7), 585-589

Production Method 3

771-50-6

942-24-5

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  2 - 3 h, 80 °C; 80 °C → rt
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 7, cooled

Reference

Preparation of indole acylhydrazone compounds for detection of organic acid by UV spectrometry

, China, , ,

Production Method 4

771-50-6

942-24-5

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Water ;  2 - 3 h, 80 °C; 80 °C → rt
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 7

Reference

Bisindole acylhydrazone and its application in preparing antibacterial drug and daily chemical product

, China, , ,

Production Method 5

1301751-01-8

942-24-5

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Dichloromethane ,  Water ;  1 min

Reference

Synthesis of N-vinyl substituted indoles and their acid-catalyzed behavior

Li, Hao; Boonnak, Nawong; Padwa, Albert, Tetrahedron Letters, 2011, 52(17), 2062-2064

Production Method 6

2260845-18-7

942-24-5

Reaction Conditions

1.1 Catalysts: Copper oxide (Cu2O) Solvents: Quinoline ;  2 h, 120 °C

Reference

Preparation method of novel indole compound with antibacterial property

, China, , ,

Production Method 7

120-72-9

942-24-5

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  30 min, rt
1.2 Reagents: Triethylborane Solvents: Hexane ;  rt; 30 min, rt
1.3 24 h, -15 °C
1.4 Reagents: Ammonium chloride Solvents: Water

Reference

Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N-H) Indoles via Common N-Indolyl Triethylborate

Zhang, Zhi-Wei; Xue, Hong; Li, Hailing; Kang, Huaiping; Feng, Juan; et al, Organic Letters, 2016, 18(15), 3918-3921

Production Method 8

494836-60-1

942-24-5

Reaction Conditions

1.1 Reagents: Carbon monoxide Catalysts: Triphenylphosphine ,  Palladium diacetate Solvents: Dimethylformamide ;  rt; 6 atm, rt → 110 °C; 72 h, 6 atm, 110 °C

Reference

Palladium-catalyzed synthesis of 3-indolecarboxylic acid derivatives

Soderberg, Bjorn C. G.; Banini, Serge R.; Turner, Michael R.; Minter, Aaron R.; Arrington, Amanda K., Synthesis, 2008, (6), 903-912

Production Method 9

771-50-6

942-24-5

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol

Reference

Diversity-oriented synthesis and antifungal activities of novel pimprinine derivative bearing a 1,3,4-oxadiazole-5-thioether moiety

Song, Zi-Long; Zhu, Yun; Liu, Jing-Rui; Guo, Shu-Ke; Gu, Yu-Cheng; et al, Molecular Diversity, 2021, 25(1), 205-221

Production Method 10

120-72-9

942-24-5

Reaction Conditions

1.1 Catalysts: Sodium chloride (exchanged products with divinylbenzene-butanediyl--bis-1vinylimidazoliumdisalicylate copolymer) ,  1H-Imidazolium, 1,1′-(1,4-butanediyl)bis[3-ethenyl-, 2-hydroxybenzoate (1:2), po… Solvents: Water ;  12 h, rt
1.2 9 h, 110 °C

Reference

Anion exchange: a novel way of preparing hierarchical porous structure in poly(ionic liquid)s

Qin, Li; Wang, Binshen; Zhang, Yongya; Chen, Li; Gao, Guohua, Chemical Communications (Cambridge, 2017, 53(26), 3785-3788

Production Method 11

131424-24-3

942-24-5

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Preparation of 3-carbomethoxyindole derivatives

, Japan, , ,

Production Method 12

108438-44-4

942-24-5

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol

Reference

Methyl group at 1-position of stabilized indole as a protective group

Nakatsuka, Shinichi; Asano, Osamu; Goto, Toshio, Heterocycles, 1986, 24(10), 2791-2

Production Method 13

771-50-6

942-24-5

Reaction Conditions

1.1 Reagents: Thionyl chloride ;  0 °C; 3 h, reflux

Reference

Synthesis of novel pyridazino[1,6-a]indole-2,4(1H,3H)-dione and pyridazino[1,6-a]indol-2(1H)-one via intramolecular electrophilic aromatic substitution

Ozdarska, Katarzyna; Petremant, Maud; Wu, Kai-Chen; Bourguet, Erika, Results in Chemistry, 2022, 4,

Production Method 14

771-50-6

942-24-5

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol ;  rt; 2 - 3 h, 80 °C

Reference

Microwave-assisted synthesis and molecular recognition properties of novel indole acylhydrazone receptors

Ye, Ying; Suo, Yourui; Yang, Fang; Yang, Yongjing; Han, Lijuan, Journal of Chemical Research, 2015, 39(5), 296-299

Production Method 15

771-50-6

942-24-5

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ;  2 - 3 h, 80 °C; 80 °C → rt
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 7, cooled

Reference

Preparation of [1,3-phenylenebis(methylidene)]bis[1H-indolyl(alkyl)carbohydrazide] as antibacterial agents

, China, , ,

Production Method 16

494836-60-1

942-24-5

Reaction Conditions

1.1 Reagents: Carbon monoxide Catalysts: Rhodium(1+), dicarbonyl(N1,N1,N2,N2-tetramethyl-1,2-ethanediamine-κN1,κN2)-, (SP… Solvents: Tetrahydrofuran ;  20 h, 100 psi, 100 °C

Reference

Ionic Diamine Rhodium Complex Catalyzed Reductive N-Heterocyclization of 2-Nitrovinylarenes

Okuro, Kazumi; Gurnham, Joanna; Alper, Howard, Journal of Organic Chemistry, 2011, 76(11), 4715-4720

Production Method 17

771-50-6

942-24-5

Reaction Conditions

1.1 Catalysts: Sulfuric acid ;  16 h, reflux; cooled
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

Synthesis and biological evaluation of novel 4,5-bisindolyl-1,2,4-triazol-3-ones as glycogen synthase kinase-3β inhibitors and neuroprotective agents

Hu, Yuanyuan; Ruan, Wenchen; Gao, Anhui; Zhou, Yubo; Gao, Lixin; et al, Pharmazie, 2017, 72(12), 707-713

Production Method 18

39891-71-9

942-24-5

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Carbon Solvents: Water ;  12 h, 0.1 MPa, 120 °C

Reference

Catalytic oxidative dehydrogenation of N-heterocycles with nitrogen/phosphorus co-doped porous carbon materials

Sun, Kangkang; Shan, Hongbin; Ma, Rui; Wang, Peng; Neumann, Helfried; et al, Chemical Science, 2022, 13(23), 6865-6872

Production Method 19

120-72-9

76-02-8

942-24-5

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Tetrahydrofuran ;  0.5 h, 0 °C
1.2 Solvents: Tetrahydrofuran ;  0 °C; 16 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
1.4 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  rt → reflux; 5 h, reflux

Reference

Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E

Abe, Takumi ; Yamada, Koji, Organic Letters, 2016, 18(24), 6504-6507

Production Method 20

74862-25-2

942-24-5

Reaction Conditions

1.1 Reagents: Water Solvents: Water

Reference

Synthesis and properties of azoles and their derivatives. 32. Synthesis and some reactions of hydrochlorides of indolylcarboxylic acid iminoesters

Kelarev, V. I.; Shvekhgeimer, G. A., Khimiya Geterotsiklicheskikh Soedinenii, 1980, (5), 645-50

Methyl indole-3-carboxylate Raw materials

• Indole
• 1H-indole-3-carboxylic acid
• Methyl indoline-3-carboxylate
• 3,3-Dimethyl 1,2-dihydro-3H-indole-3,3-dicarboxylate
• 1H-Indole-1,3-dicarboxylic acid, 3-methyl 1-(phenylmethyl) ester
• Benzeneacetic acid, α-methylene-2-nitro-, methyl ester
• methyl 1H-indole-3-carboximidoate hydrochloride
• trichloroacetyl chloride
• 1H-Indole-3-carboxylic acid, 1-[(benzoyloxy)methyl]-, methyl ester
• dimethyl 1H-indole-1,3-dicarboxylate
• Methyl 1-(1-methylethenyl)-1H-indole-3-carboxylate

Methyl indole-3-carboxylate Preparation Products

• Methyl indole-3-carboxylate (942-24-5)

• 1. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 2. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 3. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 4. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 5. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids and derivatives

Methyl indole-3-carboxylate (CAS No. 942-24-5): A Comprehensive Overview

Methyl indole-3-carboxylate, chemically identified by the CAS number 942-24-5, is a significant compound in the field of organic chemistry and pharmaceutical research. This heterocyclic compound belongs to the indole family, which is renowned for its diverse biological activities and applications in medicinal chemistry. The structure of methyl indole-3-carboxylate consists of an indole ring substituted with a carboxylate group at the 3-position and a methyl ester at the 2-position, making it a versatile intermediate in synthetic chemistry.

The< strong>Methyl indole-3-carboxylate molecule has garnered considerable attention due to its potential role in drug development. Its indole core is a common motif in natural products and pharmaceuticals, exhibiting a wide range of biological functions. Recent studies have highlighted its significance in the synthesis of bioactive molecules, particularly those targeting neurological and inflammatory disorders. The carboxylate and ester functional groups provide multiple sites for chemical modification, enabling the design of novel derivatives with enhanced pharmacological properties.

In the realm of medicinal chemistry, methyl indole-3-carboxylate serves as a crucial building block for the preparation of more complex therapeutic agents. Researchers have leveraged its structural features to develop molecules with improved solubility, bioavailability, and target specificity. For instance, derivatives of this compound have been explored as potential treatments for neurodegenerative diseases such as Alzheimer's and Parkinson's. The< strong>indole moiety, in particular, has been implicated in the modulation of neurotransmitter systems, making it an attractive scaffold for developing neuromodulatory drugs.

Recent advancements in synthetic methodologies have further enhanced the accessibility and utility of methyl indole-3-carboxylate. Catalytic processes and green chemistry approaches have enabled more efficient and sustainable routes to its synthesis, reducing environmental impact while maintaining high yields. These innovations are particularly relevant in the context of large-scale drug production, where cost-effectiveness and ecological responsibility are paramount.

The pharmacological profile of methyl indole-3-carboxylate has been extensively studied in preclinical models. Initial research suggests that it may possess anti-inflammatory and analgesic properties, making it a candidate for treating chronic pain conditions. Additionally, its interaction with various biological targets has been investigated, revealing potential applications in cancer therapy and immunomodulation. The< strong>carboxylate group plays a pivotal role in these interactions by facilitating hydrogen bonding and ionic interactions with biological receptors.

In conclusion, methyl indole-3-carboxylate (CAS No. 942-24-5) is a multifaceted compound with significant implications in pharmaceutical research and drug development. Its unique structural features and biological activities make it a valuable asset in the quest for novel therapeutic agents. As synthetic methods continue to evolve and our understanding of its pharmacology deepens, this compound is poised to play an even greater role in addressing some of the most pressing challenges in medicine today.

• 771-50-6(1H-indole-3-carboxylic acid)
• 776-41-0(Ethyl indole-3-carboxylate)
• 39830-66-5(Methyl 1H-indole-4-carboxylate)
• 227960-12-5(5-Methylindole-3-carboxylic acid methyl ester)
• 312973-24-3(Methyl 3-formyl-1H-indole-7-carboxylate)
• 197506-83-5(Methyl 3-formyl-1H-indole-5-carboxylate)
• 205873-58-1(Ethyl 1H-indole-7-carboxylate)
• 133831-28-4(Methyl 3-formylindole-6-carboxylate)
• 93247-78-0(Methyl 1H-indole-7-carboxylate)
• 50820-65-0(Methyl 1H-indole-6-carboxylate)