Tag: 100-200

On June 15, 2016, Wang, Guangyong; Li, Chaoping; Zhou, Zhiguo; Gao, Qiang; Zheng, Baofu published a patent.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the patent was Synthetic method of histone methylation enzyme EZH2 inhibitor intermediate. And the patent contained the following:

The invention relates to the synthetic method of histone methylation enzyme EZH2 inhibitor intermediate. The title synthetic method includes (1) mixing compound 1 (Z is NH, NBoc, O, etc.) with reducing agent ((R)-MeCBS-borane dimethylsulfide, sodium borohydride, etc.) in solvent (methanol, ethanol, etc.) at (-10)-0°C, stirring at 0-5°C for 10 min, quenching with hydrochloric acid at (-5)-0°C, adding Me tert-Bu ether, stirring, filtering, layering, extracting water phase with Me tert-Bu ether, collecting organic phase, washing with saturated brine, drying, filtering, and concentrating to obtain compound 2; (2) reacting with methanesulfonyl chloride in presence of base (triethylamine, N,N-diisopropylethylamine, etc.) to obtain compound 3; (3) performing nucleophilic substitution reaction with compound 4 in organic solvent (N,N-dimethylformamide, N,N-dimethylaniline, etc.) in presence of base (sodium hydrogen, sodium carbonate, etc.) at 80-130°C to obtain compound 5; and (4) performing hydrolysis. The preparation method has high product yield, simple process, convenient post treatment, readily available raw materials and environment friendliness. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Name: Methyl 2-methyl-1H-indole-3-carboxylate

The Article related to acetyl heterocycloalkane asym reduction, hydroxy ethyl heterocycloalkane stereoselective preparation methanesulfonylation, mesylate preparation indolecarboxylate nucleophilic substitution hydrolysis, histone methylation enzyme ezh2 inhibitor intermediate preparation green chem and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On May 15, 2020, Balayeva, Narmina O.; Mamiyev, Zamin; Dillert, Ralf; Zheng, Nan; Bahnemann, Detlef W. published an article.Application of 79815-20-6 The title of the article was Rh/TiO2-Photocatalyzed Acceptorless Dehydrogenation of N-Heterocycles upon Visible-Light Illumination. And the article contained the following:

Rh-photodeposited TiO2 nanoparticles selectively dehydrogenate N-heterocyclic amines I (R1 = H, 6-Me, 7-OH, etc.; R2 = H, 2-Me, 2-Ph-4-MeS), II (R3 = H, 6,7-dimethoxy; R4 = H, Ph, Me) and III (R5 = H, trifluoromethyl; R6 = H, Me, COOH, COOMe, etc.) with the concomitant generation of mol. hydrogen gas in an inert atm. under visible light (λmax = 453 nm) illumination at room temperature Initially, a visible-light-sensitive surface complex is formed between the N-heterocycle and TiO2. The acceptorless dehydrogenation of N-heterocycles is initiated by direct electron transfer from the HOMO energy level of the amine via the conduction band of TiO2 to the Rh nanoparticle. The reaction condition was optimized by examining different photodeposited noble metals on the surface of TiO2 and solvents and finding that Rh0 is the most efficient cocatalyst, and 2-propanol is the optimal solvent. Structurally diverse N-heterocycles such as tetrahydroquinolines I, tetrahydroisoquinolines II, indolines III, and others bearing electron-deficient as well as electron-rich substituents underwent the dehydrogenation in good to excellent yields. The amount of released hydrogen gas evinces that only the N-heterocyclic amines are oxidized rather than the dispersant. This developed method demonstrates how UV-active TiO2 can be employed in visible-light-induced synthetic dehydrogenation of amines and simultaneous hydrogen storage applications. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application of 79815-20-6

The Article related to quinoline preparation, tetrahydroquinoline photochem dehydrogenation rhodium titanium dioxide catalyst, tetrahydroisoquinoline photochem dehydrogenation rhodium titanium dioxide catalyst, indole preparation, indoline photochem dehydrogenation rhodium titanium dioxide catalyst and other aspects.Application of 79815-20-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On October 31, 2002, Nowak, Ireneusz; George, Clifford published an article.Quality Control of H-Idc-OH The title of the article was Stereoselective dimerization of benzylic amines derived from indoline. And the article contained the following:

Treatment of benzylic amines derived from 2-(acyloxymethyl)-5-nitroindolines with sodium hexamethyldisilazide leads to dimeric products resulting from deprotonation in the benzylic position, oxidation of the resulting carbanion to radical by the nitroarene moiety of another mol., and stereoselective radical recombination. Only those two of six possible diastereoisomers are formed in which the recombination takes place from the less hindered face in the more stable conformation of the presumably near-planar radical. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Quality Control of H-Idc-OH

The Article related to stereoselective dimerization benzylic amine indoline derivative, crystal structure bishalophenylethanediylbisindolemethanol preparation, mol structure bishalophenylethanediylbisindolemethanol preparation, radical dimerization stereochem benzylindollemethanol ester preparation and other aspects.Quality Control of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On September 21, 2016, Ji, Pengfei; Manna, Kuntal; Lin, Zekai; Urban, Ania; Greene, Francis X.; Lan, Guangxu; Lin, Wenbin published an article.Application In Synthesis of 6-Chloro-2,3-dihydro-1H-indole The title of the article was Single-Site Cobalt Catalysts at New Zr8(μ2-O)8(μ2-OH)4 Metal-Organic Framework Nodes for Highly Active Hydrogenation of Alkenes, Imines, Carbonyls, and Heterocycles. And the article contained the following:

Zirconium and hafnium metal-organic frameworks (MOF) were prepared from a tetrakis(carboxybiphenyl)methane and ZrCl4 or HfCl4; the framework contains two types of secondary building units (SBUs): cubic M8(μ2-O)8(μ2-OH)4 and octahedral M6(μ3-O)4(μ3-OH)4. While the M6-SBU is isostructural with the 12-connected octahedral SBUs of UiO-type MOFs, the M8-SBU is composed of eight MIV ions in a cubic fashion linked by eight μ2-oxo and four μ2-OH groups. Metalation of the Zr-MTBC MOF with CoCl2 followed by treatment with NaBEt3H yielded a highly active and reusable solid Zr-MOF-cobalt hydride catalyst for the hydrogenation of alkenes, imines, carbonyls, and heterocycles. The Zr-MOF-cobalt hydride catalyst tolerated a range of functional groups and was a highly active catalyst for the hydrogenation of alkenes, including tri- and tetra-substituted alkenes, with TON > 8000 for the hydrogenation of 2,3-dimethyl-2-butene. Structural and spectroscopic studies indicate that the site isolation of and open environments around the cobalt-hydride catalytic species at the cubic zirconium SBU sites of the MOF are responsible for the high catalytic activity in the hydrogenation of a wide range of challenging substrates. The structures of the zirconium and hafnium MOF and of the cobalt chloride complex of the zirconium MOF were determined by X-ray crystallog. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Application In Synthesis of 6-Chloro-2,3-dihydro-1H-indole

The Article related to zirconium hafnium tetrakiscarboxybiphenylmethane metal organic framework preparation hydrogenation catalyst, structure secondary building unit zirconium hafnium tetrakiscarboxybiphenylmethane mof, cobalt zirconium mof complex preparation chemoselective hydrogenation catalyst and other aspects.Application In Synthesis of 6-Chloro-2,3-dihydro-1H-indole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Galvan, Alicia; Calleja, Jonas; Gonzalez-Perez, Adan B.; Alvarez, Rosana; de Lera, Angel R.; Fananas, Francisco J.; Rodriguez, Felix published an article in 2015, the title of the article was Stereoselective [3+2] Carbocyclization of Indole-Derived Imines and Electron-Rich Alkenes: A Divergent Synthesis of Cyclopenta[b]indole or Tetrahydroquinoline Derivatives.Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

An unprecedented stereoselective [3+2] carbocyclization reaction of indole-2-carboxaldehydes, anilines, and electron-rich alkenes to obtain cyclopenta[b]indoles is disclosed. This pathway is different from the well-established Povarov reaction: the formal [4+2] cycloaddition involving the same components, which affords tetrahydroquinolines. Moreover, by simply changing the Bronsted acid catalyst, this multicomponent coupling process could be divergently directed towards the conventional Povarov pathway to produce tetrahydroquinolines or to the new pathway (anti-Povarov) to generate cyclopenta[b]indoles. Supported by computational studies, a stepwise Mannich/Friedel-Crafts cascade is proposed for the new anti-Povarov reaction, whereas a concerted [4+2] cycloaddition mechanism is proposed for the Povarov reaction. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to cyclopentaindole derivative stereoselective preparation, tetrahydroquinoline derivative stereoselective preparation, indolecarboxaldehyde arylamine dihydrofuran stereoselective carbocyclization, acid catalysis, divergent synthesis, heterocycles, indoles, synthetic methods and other aspects.Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei published an article in 2016, the title of the article was Ruthenium(II)-Catalyzed C-H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate-Controlled Synthesis of Indoles and 3H-Indoles.Electric Literature of 65417-22-3 And the article contains the following content:

Indoles are an important structural motif that is commonly found in biol. active mols. In this work, conditions for divergent couplings between imidamides and acceptor-acceptor diazo compounds were developed that afforded NH indoles I (R = Et, Me, tbu, Bn, Ac; R1 = H, 5-Me, 5-Br, 4-F, 6-Cl, etc) and 3H-indoles II (R = Et, Me, tBu, Bn, ipr, allyl; R1 = H, 5-Cl, 5-tbu, 5-CN, 5,6-diCl, etc) under ruthenium catalysis. The coupling of α-diazoketoesters afforded NH indoles by cleavage of the C(N2)-C(acyl) bond whereas α-diazomalonates gave 3H-indoles by C-N bond cleavage. This reaction constitutes the first intermol. coupling of diazo substrates with arenes by ruthenium-catalyzed C-H activation. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Electric Literature of 65417-22-3

The Article related to diazoketoester imidamide ruthenium activation annulation catalyst, nh indole preparation, diazomalonate imidamide ruthenium activation annulation catalyst, indole 3h preparation, c−h activation, diazo compounds, indoles, ruthenium, transition-metal catalysis and other aspects.Electric Literature of 65417-22-3

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On July 1, 2010, Suga, Hiroyuki; Arikawa, Tadashi; Itoh, Kennosuke; Okumura, Yukihisa; Kakehi, Akikazu; Shiro, Motoo published an article.Category: indole-building-block The title of the article was Asymmetric 1,3-dipolar cycloaddition reactions of azomethine imines with acrolein catalyzed by L-proline and its derivatives. And the article contained the following:

1,3-Dipolar cycloadditions between acrolein and various N,N’-cyclic azomethine imines in the presence of L-proline and its derivatives as organocatalysts were investigated. Reactions that were catalyzed by (S)-indoline-2-carboxylate (30 mol%) in CHCl3/MeOH 97:3 (volume/volume) showed high exo-selectivities (exo/endo 91:9∼99:1) and enantioselectivities (75∼98% ee). In contrast, reactions catalyzed by L-proline (30 mol%) under similar conditions favored the endo-cycloadduct (83:27∼99:1) with modest to good enantioselectivities (31∼83% ee). The diastereoselective mechanism of the L-proline-catalyzed reaction was found to involve the isomerization of the exo- to the endo-cycloadduct in the presence of L-proline. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Category: indole-building-block

The Article related to azomethine imine acrolein asym dipolar cycloaddition proline catalyst, indolinecarboxylate catalyst asym dipolar cycloaddition azomethine imine acrolein, hydropyrazolopyrazole asym synthesis isomerization, pyrazolopyrazole hydro asym synthesis isomerization and other aspects.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Hayashi, Shigeo; Ohashi, Katsuyo; Nakata, Eriko; Emoto, Chie published an article in 2012, the title of the article was Discovery of 1-(β-amino substituted-β-alanyl)-N,N-dimethylindoline-2-carboxamides as novel nonpeptide antagonists of nociceptin/orphanin FQ receptor: Efficient design, synthesis, and structure-activity relationship studies.SDS of cas: 79815-20-6 And the article contains the following content:

Since the discovery of endogenous nociceptin/orphanin FQ (N/OFQ) peptide and N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], the structures, distribution, and pharmacol. have been reported in detail. N/OFQ and NOP receptor are located in the corticolimbic regions that are involved in the integration of the emotional activity, and located in the spinal cord, the peripheral nervous systems or other peripheral tissues that are related to pain as well as urinary signal transmissions, with a pattern distinct from that of classical opioid peptides and their receptors in rodents or primates. Furthermore, N/OFQ-NOP receptor system plays an important role in the regulation of various human physiologies such as depression effect, hyperphasia effect, and blood pressure effect. In this study, the structure-activity relationship of novel NOP receptor antagonist for various 1-(β-amino substituted-β-alanyl)-N,N-dimethylindoline-2-carboxamides was investigated in vitro to elucidate structural requisites to identify and develop potent and selective NOP receptor antagonists, which resulted in the discovery of 1-{3-[4-(substituted phenyl)piperidin-1-yl]propanoyl}-N,N-dimethylindoline-2-carboxamide analogs that display potent and selective human NOP (hNOP) receptor binding affinity and potent hNOP receptor antagonist activity. The efficient design, synthesis, and structure-activity relationship studies for potent and selective novel NOP receptor antagonists and significant findings in vitro, that include insights for binding and functional mechanisms via receptor-ligand interactions, are reported herein. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).SDS of cas: 79815-20-6

The Article related to peptidomimetic synthesis nofq nop receptor antagonist structure activity pharmacokinetics, amino alanyl dimethylindoline carboxamide parallel synthesis metabolic stability lipophilicity, indoline carboxylic acid amidation amine michael addition drug design and other aspects.SDS of cas: 79815-20-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On November 30, 2022, Riegel, George F.; Payne, Curtis; Kass, Steven R. published an article.Safety of H-Idc-OH The title of the article was Effects of Broensted acid cocatalysts on the activities and selectivities of charge-enhanced thiourea organocatalysts in Friedel-Crafts and oxa-Pictet-Spengler reactions. And the article contained the following:

Charge-enhanced chiral thioureas were used in the organocatalysis of the Friedel-Crafts alkylation of indole with trans-β-nitrostyrene and the oxa-Pictet-Spengler reaction of tryptophol and benzaldehyde. The effects of substoichiometric Broensted acidic additives on the reaction conversions and enantiomeric ratios of these transformations were examined and the role of these species in the mechanism of the latter reaction was explored using variable time normalization kinetics to elucidate the reaction order of the catalyst, cocatalyst and reagents. A proposed pathway for the oxa-Pictet-Spengler cyclization that involves matched and mismatched catalyst and cocatalyst pairs and an off-cycle racemization of the latter species was provided. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Safety of H-Idc-OH

The Article related to nitrostyrene indole thiourea organocatalyst enantioselective friedel crafts alkylation, nitro phenyl ethyl indole preparation, benzaldehyde tryptophol thiourea organocatalyst enantioselective oxa pictet spengler reaction, phenyl pyranoindole preparation and other aspects.Safety of H-Idc-OH

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On April 20, 2017, Lin, Wenbin; Manna, Kuntal; Ji, Pengfei published a patent.Category: indole-building-block The title of the patent was Stabilization of active metal catalysts at metal-organic framework nodes for highly efficient organic transformations. And the patent contained the following:

Metal-organic framework (MOFs) compositions based on post not synthetic metalation of secondary building unit (SBU) terminal or bridging OH or OH2 groups with metal precursors or other post-synthetic manipulations are described. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asym. organic transformations, including the regioselective borylation and silylation of benzyiic C-H bonds, the hydrogenation of aikenes, imines, carbonyls, nitroarenes, and heterocycles, hydroboration, hydrophosphination, and cyclization reactions. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Category: indole-building-block

The Article related to zirconium cobalt benzenebisphenylcarboxylato terphenyldicarboxylato methanetetrakisbiphenylcarboxylato trimesato biphenyldicarboxyiato complex preparation, catalyst zirconium cobalt benzenebisphenylcarboxylato trimesato biphenyldicarboxyiato complex and other aspects.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles