Category: indole-building-block

Bakke, Jan published an article in 1974, the title of the article was New syntheses of substituted indoles.Application of 52537-00-5 And the article contains the following content:

The indoles I (R = H, 4-Cl, 6-Cl, 4-NH2) were prepd by cyclizing RC6H3(CH2CH2Cl)(NO2)-1,2 (R = H, 6-Cl, 4-Cl, 6-O2N) with Fe and dehydration of the resulting dehydroindole with Pd/C. o-O2NC6H4Me was condensed with PhCHO to give o-O2NC6H4CH2(O)HPh which was oxidized with concentrated HNO3 and the product cyclized by catalytic reduction to give 2-phenylindole. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Application of 52537-00-5

The Article related to indole chloro phenyl, phenethyl chloride nitro cyclization, cyclization nitrophenethyl chloride, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Application of 52537-00-5

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 January 19, 1995, Ham, Peter; Jones, Graham Elgin; Forbes, Ian Thomson published a patent.Recommanded Product: 6-Chloro-2,3-dihydro-1H-indole The title of the patent was Indoline derivatives as 5-HT2C antagonists. And the patent contained the following:

Title compounds I and salts thereof are claimed [wherein P = Ph, quinoline, isoquinoline, or 5- or 6-membered aromatic heterocycle containing 1-3 N, O, and/or S atoms; R1 = H, C1-6 alkyl, halo, CF3, NR7R8, OR9; R7, R8, R9 = independently H, C1-6 alkyl, aryl-C1-6-alkyl; R2 = H, C1-6 alkyl; R3 = C1-6 alkyl; n = 0-3; m = 0-4; and R4 groups = independently C1-6 alkyl or haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6-cycloalkyl-C1-6-alkyl, C1-6 alkylthio, C3-6 cycloalkylthio, C3-6-cycloalkyl-C1-6-alkylthio, halo, nitro, CF3, OCF3, SCF3, SO2CF3, SO2F, formyl, C2-6 alkanoyl, cyano, optionally substituted Ph or thienyl, NR7R8, CONR7R8, OR9, CO2R10; R10 = H, C1-6 alkyl]. I have 5-HT2C receptor antagonist activity, and some compounds also exhibit 5HT2B antagonist activity, making them potentially useful for treating a variety of central nervous and digestive system disorders. For example, reaction of 6-chloro-5-methylindoline [preparation given] with 3-pyridyl isocyanate [prepared from nicotinoyl azide in refluxing toluene] gave 62% title compound II. Testing of II in the Geller Seifter procedure [see WO 94/04533] showed a significant increase in punished responding at 0.5-10 mg/kg orally. Examples include 45 syntheses, 85 precursor preparations, and three formulations. I had pKi of 6.1-8.7 in an in vitro test for binding of [3H]-mesulergine to rat or human 5-HT2C clones, and selected I had ID50 of 0.6-15.9 mg/kg orally for reversal of MCPP-induced hypolocomotion in another bioassay. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Recommanded Product: 6-Chloro-2,3-dihydro-1H-indole

The Article related to indoline 5ht2c receptor antagonist preparation, serotoninergic receptor antagonist preparation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Recommanded Product: 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

On October 2, 2008, Boehm, Jeffrey Charles; Busch-Petersen, Jakob; Fu, Wei; Jin, Qi; Kerns, Jeffrey K.; Li, Huijie; Lin, Guoliang; Lin, Xichen; Neipp, Christopher E. published a patent.COA of Formula: C10H10BrNO2 The title of the patent was Preparation of indolecarboxamide derivatives for use as IKK2 inhibitors. And the patent contained the following:

Title compounds I [R1 = YZ; R2 = bicyclo group or (un)substituted heterocycloalkyl containing S, S(O), or SO2; R3 and R4 independently = H or F; Y = bond, alkylene, alkenylene, or alkynylene; Z = (un)substituted aryl or heteroaryl; m = 0 or 1; with provisions], and their pharmaceutically acceptable salts, are prepared and disclosed as IKK2 inhibitors. Thus, e.g., II was prepared by bromination of 1-(1,1-dimethylethyl) 7-Me 2,3-dihydro-1H-1,7-dicarboxylate (preparation given) followed by deprotection, oxidation, condensation with tetrahydro-4H-thiopyran-4-one, protection, oxidation, deprotection/hydrolysis, amidation with ammonia, and coupling with phenylboronic acid. Select I were evaluated in IKK2 assays and demonstrated a pIC50 of about 5.0 to about 8.5. I were disclosed as therapeutic agents for the inhibition of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, rhinitis, and chronic obstructive pulmonary disease. The experimental process involved the reaction of Methyl 5-bromoindoline-7-carboxylate(cas: 860624-88-0).COA of Formula: C10H10BrNO2

The Article related to indolecarboxamide derivative preparation ikk2 inhibitor rheumatoid arthritis asthma rhinitis, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.COA of Formula: C10H10BrNO2

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 1, 2020, Thombal, Raju S.; Lee, Yong Rok published an article.COA of Formula: C11H11NO2 The title of the article was Palladium-Catalyzed Direct Oxidative C-H Activation/Annulation for Regioselective Construction of N-Acylindoles. And the article contained the following:

A Pd(II)-catalyzed C(sp3)-H/C(sp2)-H coupling/annulation of anilides and α-dicarbonyl compounds for the synthesis of diverse N-acyl indoles was described. The reaction was achieved by cascade C-H activation, coupling, and intramol. cyclization. This protocol provided a variety of indoles with high functional group tolerance and excellent regioselectivity. The utility of this protocol was demonstrated by transforming the synthesized compound into diversely functionalized analogs. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).COA of Formula: C11H11NO2

The Article related to acylindole regioselective preparation, anilide dicarbonyl compound coupling intramol cyclizn, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.COA of Formula: C11H11NO2

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 March 31, 1990, Sakamoto, Takao; Nagano, Tatsuo; Kondo, Yoshinori; Yamanaka, Hiroshi published an article.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Condensed heteroaromatic ring systems. XVII. Palladium-catalyzed cyclization of β-(2-halophenyl)amino substituted α,β-unsaturated ketones and esters to 2,3-disubstituted indoles. And the article contained the following:

Palladium-catalyzed cyclization of β-(2-halophenyl)amino substituted α,β-unsaturated ketones and esters, prepared from 2-haloanilines by three different methods, gave 2,3-disubstituted indoles. Thus, conductivity of 2-IC6H4NH2 with AcCH2Ac in C6H6 containing catalyst 4-MeC6H4SO3H gave 72% 2-IC6H4NHCMe:CHCOMe which on cyclization with Pd(OAc)2 in Et3N-DMF in a sealed tube (120°, 6 h) gave 49% 3-acetyl-2-methylindole. 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 halophenylaminoalkenone preparation palladium catalyzed cyclization, acylindole, indole acyl, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles 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 July 12, 2022, Hou, Wei; Dong, Hewei published a patent.Category: indole-building-block The title of the patent was Green preparation method of off-DNA and on-DNA arylselenyl indole compounds and its applications. And the patent contained the following:

The present invention relates to the green preparation method of off-DNA and on-DNA arylselenyl indole compounds and its applications. In particular, preparation method comprises of indole compounds, benzisoselenazolone compounds and the Lewis acid are dissolved in a solvent, and the reaction is stirred for 1 to 12 h at -20 to 65°C, to obtain 3-arylselenoindole compounds I (wherein, R1 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, etc.; R2 is selected from hydrogen, C1-C4 alkyl, unsubstituted or halogenated, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4alkoxy, etc.; R3 is selected from the one in hydrogen, halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkyl, C1-C4 haloalkyl, nitro, carboxyl, C1-C4 alkoxycarbonyl; R4 is selected from hydrogen, C3-C8 cycloalkyl, unsubstituted or halogenated, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, etc.). Similarly, preparation method of on-DNA arylselenyl indole compounds comprises of on-DNA indole compounds, benzisoselenazolone compounds and the Lewis acid are dissolved in a solvent to construct a reaction system, react at 15-50°C for 0.5 to 24 h, the gained reaction solution is after post-processing, obtain compounds II (R5 consists of 0-10 atoms, when the skeleton of R5 consists of 0 atoms, the carbonyl group is directly connected to the indolyl group; when the skeleton of R5 consists of 1-10 atoms, the group is any one of the -CH2-, CF2-, -CH2-O-, etc.; R6 is selected from a kind of in hydrogen, halogen, C1-C6 alkyl,nitro, etc.; R7 is selected from hydrogen, one of C1-C6 alkyl, C1-C6 haloalkyl, Ph, etc.; R8 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, halogen, C1-C6 alkoxy group etc.; R9 is selected from hydrogen, C6-C10 aryl, C1-C6 alkyl, etc.). The inventive method has advantages of only needs to add catalytic amount of lewis acid catalyst, the catalyst is cheap and easy to get, simple reaction system, the reaction is to air and water tolerance, doesn’t need inert gas protection, the reaction solvent without removing water, easy to operate; reaction condition is gentle, reaction yield is high and has excellent functional group tolerance; this synthetic method is also applicable to synthesis of porous plate parallel; product is single, and the organic solvent/water mixed phase to carry out, the operation is simple, does not introduce metal reagent, environment friendly, it is applicable to use a perforated plate for the DNA encoding the synthesis of compound library. The experimental process involved the reaction of 6-Chloro-1H-indole-5-carboxylic acid(cas: 256935-86-1).Category: indole-building-block

The Article related to arylselenyl indole green preparation selenization antitumor agent, dna conjugated arylselenyl indole green preparation selenization, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles 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

On November 30, 1977, Bergman, Jan; Carlsson, Rene; Sjoberg, Birger published an article.Safety of Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was The reaction of indole and the indole Grignard reagent with phosgene. A facile synthesis of indole-3-carboxylic acid derivatives. And the article contained the following:

Indole-3-carboxylic and indole-3-glyoxylic acid derivatives were prepared from indoles or oxindoles and phosgene or oxalyl chloride. In this reaction, the indole Grignard reagent gave several products, including the cyclotetramers I (X = CO, COCO). Indolo-fused heterocycles were also prepared by this reaction. Thus, phosgene and 2-(2-hydroxyphenyl)-N-methylindole gave 5,6-dihydro-11-methyl-6-oxobenzo[a]pyrano[4,3-b]indole (II). The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Safety of Methyl 2-methyl-1H-indole-3-carboxylate

The Article related to indole reaction phosgene, oxindole reaction phosgene, oxalyl chloride reaction indole, grignard indole phosgene, benzopyranoindole, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Safety of 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 February 15, 2012, Lin, Ning; Luo, Ren-shi; Chen, Miao-miao; Lu, Gui published an article.COA of Formula: C9H9NO2 The title of the article was Synthesis and characterization of two chiral indoline derivatives. And the article contained the following:

Two indoline carboxylic acid derivatives (S)-(1-methylindolin-2-yl)diphenylmethanol and (S)-2-(1-methylindolin-2-yl)-1,3-diphenylpropan-2-ol were synthesized from (S)-indoline-2-carboxylic acid, through the N-methylation, esterification and Grignard addition The total yields of the two products were 86.5% and 89.7% resp. The structures of product were confirmed by 1HNMR, 13CNMR and HRMS. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).COA of Formula: C9H9NO2

The Article related to chiral indolinecarboxylic acid methylation esterification addition, methylindolinyl diphenylmethanol diphenylpropanol preparation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.COA of Formula: C9H9NO2

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 28, 2005, Baldwin, Ian Robert; Bamborough, Paul; Christopher, John Andrew; Kerns, Jeffrey K.; Longstaff, Timothy; Miller, David Drysdale published a patent.Name: Methyl 5-bromoindoline-7-carboxylate The title of the patent was Preparation of 7-indolecarboxamides as IKK2 kinase inhibitors for the treatment of such as inflammatory and tissue repair disorders. And the patent contained the following:

Title compounds I [wherein R1, R2 = H, halo, alkylene, alkenylene, (hetero)aryl, etc., and salts, solvates, or physiol. functional derivatives thereof] were prepared as IKK2 kinase inhibitors. For instance, Pd-catalyzed coupling of Boc-protected bromide II (preparation given) with phenylboronic acid followed by deprotection with HCl gave 7-indolecarboxamide III. Most invented compounds were found to have activity >4.8 in the IKK2 assay, in which the degree of phosphorylation of GST-IκBα was measured as a ratio of specific 665 nm energy transfer signal to reference europium 620 nm signal. Therefore, I and their pharmaceutical compositions are useful in the treatment and prevention of disease states mediated by IKK2 mechanisms, including inflammatory and tissue repair disorders. The experimental process involved the reaction of Methyl 5-bromoindoline-7-carboxylate(cas: 860624-88-0).Name: Methyl 5-bromoindoline-7-carboxylate

The Article related to indolecarboxamide preparation ikk2 kinase inhibitor, treatment inflammatory tissue repair disorder indolecarboxamide preparation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Name: Methyl 5-bromoindoline-7-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 October 14, 2004, Nobayashi, Eiji; Fujii, Katsuhiro published a patent.Category: indole-building-block The title of the patent was Preparation of high-purity indolecarboxylic acids from their esters. And the patent contained the following:

Title carboxylic acids are prepared by hydrolysis of their esters I [R1-R6 = H, halo, alkyl, acyl(oxy), alkoxy, aryl, NO2, cyano, etc.; ≥1 of R1-R6 = carboxylic acid ester residue; R7 = H, C1-4 alkyl] with alkali metal hydroxides in nonpolar solvents, H2O, and alcs. Thus, Et 1-methylindole-2-carboxylate was treated with 4.8% aqueous NaOH at 55-59° in MePh and MeOH for 3 h, the organic phase removed, and acidified to give 95% 1-methylindole-2-carboxylic acid with 99.0% purity. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Category: indole-building-block

The Article related to indolecarboxylic acid preparation solvent nonpolar alc water, toluene methanol water solvent hydrolysis indolecarboxylate ester, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles 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