01/11/2022 - Page 2 of 3 - Indole Building Blocks

Sakamoto, Takao et al. published their research in Synthesis in 1990 |CAS: 65417-22-3

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

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

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

Thombal, Raju S. et al. published their research in Organic Letters in 2020 |CAS: 65417-22-3

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

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

Boehm, Jeffrey Charles et al. published their patent in 2008 |CAS: 860624-88-0

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

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

Ham, Peter et al. published their patent in 1995 |CAS: 52537-00-5

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

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

Bakke, Jan et al. published their research in Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry in 1974 |CAS: 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

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

Albaugh, Pamela Ann et al. published their patent in 2003 |CAS: 52537-00-5

The Article related to indolyl heteroaryl pyrroledione preparation gsk3beta inhibitor antidiabetic alzheimer’s disease, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.SDS of cas: 52537-00-5

On September 18, 2003, Albaugh, Pamela Ann; Ammenn, Jochen; Burkholder, Timothy Paul; Clayton, Joshua Ryan; Conner, Scott Eugene; Cunningham, Brian Eugene; Engler, Thomas Albert; Furness, Kelly Wayne; Henry, James Robert; Li, Yihong; Malhotra, Sushant; Tebbe, Mark Joseph; Zhu, Guoxin published a patent.SDS of cas: 52537-00-5 The title of the patent was Preparation of 3-(indol-3-yl) 4-heteroaryl substituted pyrrole-2,5-diones as GSK-3β inhibitors. And the patent contained the following:

The title compounds [I; Ar = (un)substituted benzofuryl, indolyl, quinolinyl, etc.; R1 = H, alkoxy, halo, etc.; R2 = H, alkyl, (un)substituted piperidin-4(or 3)-yl, etc.; R3 = H, halo, alkyl, cyclopropyl; or R2 and R3 taken together = CH2CH2CH(CH2OH)CH2; R4, R5 = H, halo], useful for treating GSK-3β mediated diseases such as diabetes and Alzheimer’s disease, were prepared Thus, reacting 2-[1-(3-hydroxypropyl)-1H-indol-3-yl]acetamide with Me (1-methyl-1H-indol-4-yl)oxoacetate in the presence of tert-BuOK in DMF afforded 54% I [Ar = 1-methyl-1H-indol-4-yl; R1, R3-R5 = H; R2 = 3-hydroxypropyl] which showed IC50 of 0.1757 μM against GSK-3β. Pharmaceutical composition comprising the compound I was claimed. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).SDS of cas: 52537-00-5

Vu, Cuong M. et al. published their research in Tetrahedron Letters in 2020 |CAS: 65417-22-3

The Article related to indole preparation, haloaniline diketone heterocyclization copper ferrite nanocatalyst recycling, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.COA of Formula: C11H11NO2

On December 10, 2020, Vu, Cuong M.; Le, Khoa B.; Vo, Uyen N.; Van, Vy D. T.; Nguyen, Anh T.; Phan, Nam T. S.; Le, Nhan T. H.; Nguyen, Tung T. published an article.COA of Formula: C11H11NO2 The title of the article was Recyclable CuFe2O4 for the synthesis of 2,3-disubstituted indoles. And the article contained the following:

A method for the CuFe2O4-catalyzed coupling of 2-iodo- or 2-bromoanilines 2-X-RC6H3NH2 (R = H, 4-trifluoromethoxy, 5-trifluoromethyl, etc.; X = I or Br) and acetylacetone or isosteric 1,3-diketones R1C(O)CH2C(O)R2 (R1 = Me, ethyl; R2 = ethoxy, methoxy) to afford 2,3-disubstituted indoles I (R3 = H, 5-bromo, 6-Me, etc.) has been developed. The superparamagnetic material showed superior activity in comparison to other ferrites or copper-based metal-organic frameworks. Functionalities including ester, cyano, and halogen groups were compatible with the reaction conditions. The CuFe2O4 catalyst was easily recoverable and reusable and offers a convenient pathway to afford synthetically useful heterocycles. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).COA of Formula: C11H11NO2

Dugar, Sundeep et al. published their patent in 2002 |CAS: 256935-86-1

The Article related to indolecarboxamide preparation p38alpha inhibitor, antiinflammatory indolecarboxamide preparation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Formula: C9H6ClNO2

On June 6, 2002, Dugar, Sundeep; Mavunkel, Babu J.; Luedtke, Gregory R.; Mcenroe, Glen published a patent.Formula: C9H6ClNO2 The title of the patent was Preparation of indolecarboxamides as p38-α inhibitors. And the patent contained the following:

Title compounds were prepared as p38-α inhibitors (no data). Thus, 6-chloro-1-methyl-1H-indole-5-carboxylic acid was amidated by (R)-3-aminomethyl-1-benzylpyrrolidine followed by acylation and amidation to give title compound I. The experimental process involved the reaction of 6-Chloro-1H-indole-5-carboxylic acid(cas: 256935-86-1).Formula: C9H6ClNO2

Wang, Zechao et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2018 |CAS: 65417-22-3

The Article related to indole hexaketocyclohexane alc copper catalyst alkoxycarbonylation, indolyl oxoacetate preparation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Quality Control of Methyl 2-methyl-1H-indole-3-carboxylate

Wang, Zechao; Yin, Zhiping; Wu, Xiao-Feng published an article in 2018, the title of the article was Copper-catalyzed carbonylative transformations of indoles with hexaketocyclohexane.Quality Control of Methyl 2-methyl-1H-indole-3-carboxylate And the article contains the following content:

With hexaketocyclohexane octahydrate as the carbon monoxide source, a novel procedure for copper-catalyzed direct double carbonylation of indoles was established. Using alcs. as reaction partners, moderate to good yields of the desired double carbonylation products were obtained. Wide functional group tolerance and substrate scope was observed The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Quality Control of Methyl 2-methyl-1H-indole-3-carboxylate

Tanimori, Shinji et al. published their patent in 2008 |CAS: 65417-22-3

The Article related to indole compound preparation, haloaniline cyclocondensation oxochlorobutanoate cuprous iodide catalyst, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate

On May 8, 2008, Tanimori, Shinji; Kirihata, Mitsunori published a patent.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the patent was Preparation of indole compounds by cyclocondensation of haloanilines. And the patent contained the following:

Title compounds I [R1 = (un)substituted alkyl, cycloalkyl, heterocyclyl, alkynyl, alkoxy, aryl ether group, cyano, carboxyl, carbamoyl, etc.; R2 electron-withdrawing group; R3 = H, any group given for R2; n = 0-4], useful as intermediates for drugs, agrochems., electronic materials, etc., are prepared by reacting haloanilines II (R3, n = same as above; Hr = halo) with R1COCH2R2 (R1, R2 = same as above) in the presence of catalysts. Thus, Me 3-oxo-4-chlorobutanoate was added dropwise to a mixture of NaH and DMSO and the reaction mixture was treated with 2-IC6H4NH2, CuI, and L-proline at room temperature for 5 h to give 23% Me 2-chloromethyl-1H-indole-3-carboxylate. 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