Category: 65417-22-3

Whalley, W. B. published an article in 1951, the title of the article was Organic fluoro compounds. V. ω-Trihaloacetophenones.HPLC of Formula: 65417-22-3 And the article contains the following content:

cf. C.A. 45, 9001b. 6,2,4-MeO(HO)2C6H2CO2Me (I) (2.2 g.), 0.7 g. Ac2O, and 15 mL. AcOH, saturated with BF3 and the precipitate crystallized from MeOH, give 2.2 g. Me 3-acetyl-2,4-dihydroxy-6-methoxybenzoate (II), m. 170°; II results also from 1.7 g. I, 10 mL. MeCN, 4 g. ZnCl2, and 2 g. AlCl3 in 100 mL. ether saturated with HCl at 5° and the ketimine salt hydrolyzed after 24 h. with H2O. Hydrolysis of II with KOH gives 4,2,6-MeO(HO)2C6H2Ac (III), m. 137°. 4,2,6-MeO(HO)2C6H2COCCl3 (2 g.), 0.7 g. Ac2O, and 5 mL. AcOH, saturated with BF3, give 2.2 g. 2,6-dihydroxy-4-methoxy-3-trichloroacetylacetophenone (IV), fawn, m. 115°; hydrolysis with aqueous KOH gives III; 0.5 g. IV in 7 mL. MeOH containing 1 drop 60% KOH, refluxed 5 min., gives a quant. yield of II; warmed with 2 N NaHCO3, IV gives 3-acetyl-2,4-dihydroxy-6-methoxybenzoic acid, m. 182° (decomposition). Reduction of IV with Zn in AcOH gives a quant. yield of 3,4,2,6-Ac(MeO)(HO)2C6HAc, m. 105°. I (2.2 g.), 1.5 g. Zn(CN)2, and 10 mL. HCN in 120 mL. ether, saturated with HCl, give 2 g. of the 3-formyl derivative (V); 2 g. V in 40 mL. MeOH, added (5 min.) to 20 mL. concentrated HCl and 10 mL. H2O containing 15 g. amalgamated Zn and heated 5 min., give 1.6 g. Me 2,4-dihydroxy-6-methoxy-3-methylbenzoate (VI), m. 202°, gives a violet FeCl3 reaction; hydrolysis of VI with aqueous KOH gives 2,5,1,3-Me(MeO)C6H2(OH)2, m. 124°. VI (0.75 g.) with HCN and Zn(CN)2 give 0.6 g. of the 5-formyl derivative, m. 122°, gives a brown-violet FeCl3 reaction; 2,4-dinitrophenylhydrazone, orange, m. 262-3° (decomposition). 3,5-(MeO)2C6H3OH (5 g.), 5 g. ZnCl2, 10 g. Cl3CCN, and 100 mL. ether, saturated at 5° with HCl and the products hydrolyzed after 24 h., give 3.7 g. α,α,α-trichloro-4-hydroxy-2,6-di-methoxyacetophenone (VII), pale yellow, m. 117°; with warm 2 N NaOH, VII gives a quant. yield of 4,2,6-HO(MeO)2C6H2CO2H, m. 201°; reduction of VII with Zn and HCl in MeOH gives a quant. yield of 2-ethylphloroglucinol 1,3-di-Me ether (VIII), m. 153°; 0.6 g. VII, 2 g. Zn, and 5 mL. AcOH, refluxed 30 min., give VIII; addition of 2 g. Zn (3 min.) to 0.6 g. VII in 5 mL. AcOH and heating 2 min. on the steam bath give a quant. yield of 4,2,6-HO(MeO)2C6H2Ac. 3,5-(MeO)2C6H2OH (2.5 g.) and 2 g. ZnCl2 in 50 mL. ether, saturated at room temperature with HCl, treated with 6 g. F3CCN, the product (after 4 h.) hydrolyzed (15 min.) with H2O, and the solid (1.5 g.) distilled with steam, give 0.2 g. α,α,α-trifluoro-2-hydroxy-4,6-dimethoxyacetophenone, bright yellow, m. 87° (red-brown FeCl3 reaction), and 1 g. α,α,α-trifluoro-4-hydroxy-2,6-dimethoxyacetophenone, m. 155°. 2,1,3,5-Me(MeO)C6H2(OH)2 (1.4 g.) gives 0.5 g. α,α,α-trifluoro-2,6-dihydroxy-4-methoxy-3-methylacetophenone, bright yellow, m. 145°, gives an intense violet-brown FeCl3 reaction. 2,3,1,5-Me(HO)C6H2(OMe)2 (1.1 g.) gives 0.75 g. α,α,α-trifluoro-2-hydroxy-4,6-dimethoxy-3-methylacetophenone, bright yellow, m. 100°, gives an intense green-brown FeCl3 reaction. 2-Methyl-3-trichloroacetylindole (0.5 g.) in 17 mL. MeOH containing 1 drop 60% KOH, refluxed 5 min., gives a quant. yield of Me 2-methyl-3-indolecarboxylate, m. 165°. 2,6-(HO)2C6H3Ac (2.5 g.) and 2 g. BrCH2CO2Et in 100 mL. Me2CO containing 20 g. K2CO3, refluxed 3 h., give 2.9 g. Et (2-acetyl-3-hydroxyphenoxy)acetate (IX), m. 74-5°, gives a deep crimson FeCl3 reaction; 1 g. ester, hydrolyzed (30 min.) on the steam bath with 10 mL. 2 N NaOH, the acid refluxed 80 min. with 2.5 g. AcONa and 8 g. Ac2O, and the ester hydrolyzed (1 h. on the steam bath) with 2 N NaOH, gives 0.4 g. 4-hydroxy-3-methylbenzofuran (X), m. 111°. X (2.1 g.), 4 g. ZnCl2, and 4 g. Cl3CCN in ether, saturated at 5° with HCl and the ketimine hydrolyzed with H2O, give 1.7 g. of the 2-trichloroacetyl derivative (XI), bright green, m. 159°; with EtOH containing a little 60% KOH XI yields 2-carbethoxy-4-hydroxy-3-methylbenzofuran (XII), m. 155°; 2 g. IX in 15 mL. EtOH containing EtONa (0.2 g. Na), refluxed 1 h., gives 0.2 g. XII. 2,4-(MeO)2C6H3COCF3 yields a 2,4-dinitrophenylhydrazone, orange, m. 195°; the dinitrophenylhydrazone of 6-methoxy-2-(trifluoroacetyl)benzofuran, blood-red, m. 190-1° (decomposition). The theor. implications of the bright color and the reactions of the α,α,α-trichloro-and α,α,α-trifluoropolyhydroxyacetophenones and their derivatives are discussed. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).HPLC of Formula: 65417-22-3

Methyl 2-methyl-1H-indole-3-carboxylate(cas:65417-22-3) belongs to indole. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. HPLC of Formula: 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 September 1, 2015, Gehling, Victor S.; Vaswani, Rishi G.; Nasveschuk, Christopher G.; Duplessis, Martin; Iyer, Priyadarshini; Balasubramanian, Srividya; Zhao, Feng; Good, Andrew C.; Campbell, Robert; Lee, Christina; Dakin, Les A.; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Audia, James E.; Cummings, Richard T.; Normant, Emmanuel; Trojer, Patrick; Albrecht, Brian K. published an article.Quality Control of Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Discovery, design, and synthesis of indole-based EZH2 inhibitors. And the article contained the following:

The discovery and optimization of a series of small mol. EZH2 inhibitors is described. Starting from dimethylpyridone HTS hit, a series of indole-based EZH2 inhibitors were identified. Biochem. potency and microsomal stability were optimized during these studies and afforded compound (I). Compound I demonstrates nanomolar levels of biochem. potency (IC50 = 0.002 μM), cellular potency (EC50 = 0.080 μM), and afforded tumor regression when dosed (200 mpk SC BID) in an EZH2 dependent tumor xenograft model. 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

The Article related to indole derivative preparation sar ezh2 inhibitor anticancer mao cell, ezh2, epigenetics, histone methyltransferase, prc2, pyridone, Pharmacology: Structure-Activity and other aspects.Quality Control 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

Huang, Xu-Lun; Cheng, Yuan-Zheng; You, Shu-Li published an article in , the title of the article was Visible-light enabled synthesis of cyclopropane-fused indolines via dearomatization of indoles.HPLC of Formula: 65417-22-3 And the article contains the following content:

An efficient synthesis of methylene-unsubstituted cyclopropane-fused indolines I (R1 = H, 2-Br, 3-Me, etc.; X = N, CH; R2 = H, CO2Me, Ac, 2-hydroxyethyl; R3 = H, Me; R4 = Boc, Ts, Ac, 4-acetyl-10,10-dimethyl-3-thia-4-azatricyclodecane-3,3-dione) and (R)-1a-((1R,5S)-10,10-dimethyl-3,3-dioxo-3lambda*6*-thia-4-aza-tricyclo[5.2.1.0*1,5*]decane-4-carbonyl)-1a,6a-dihydro-1H-6-aza-cyclopropa[a]indene-6-carboxylic acid tert-Bu ester via photoredox catalyzed dearomative cyclopropanation of indole derivatives II was developed. A broad range of indoles bearing a variety of functional groups was compatible with these mild conditions, affording the products in moderate to excellent yields. Asym. cyclopropanation was also realized with the assistance of a chiral auxiliary in good yield with excellent diastereoselectivity, followed by the removal of the auxiliary to give enantioenriched alc. I. The 5 mmol scale reaction and derivatizations of the products I were successfully carried out to demonstrate the synthetic value of this reaction. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).HPLC of Formula: 65417-22-3

The Article related to cyclopropane indoline preparation diastereoselective, indole preparation iodomethylsilicate dearomative cyclopropanation photoredox catalyst, Placeholder for records without volume info and other aspects.HPLC of Formula: 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 April 5, 2019, Shi, Yao; Wong, Jonathan; Ke, Zhihai; Yeung, Ying-Yeung published an article.SDS of cas: 65417-22-3 The title of the article was Lipophilic Indole-Catalyzed Intermolecular Bromoesterification of Olefins in Nonpolar Media. And the article contained the following:

An environmentally benign and highly versatile catalytic protocol has been successfully applied in the intermol. bromoesterification between various olefins and carboxylic acids. The use of a highly lipophilic indole catalyst and 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as the bromine source allows the reaction to proceed in heptane via a solid-liquid phase transfer mechanism, affording the corresponding bromoester products in good-to-excellent yields. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).SDS of cas: 65417-22-3

The Article related to lipophilic indole catalyst intermol bromoesterification olefin nonpolar media, bromoester preparation, General Organic Chemistry: Synthetic Methods and other aspects.SDS of cas: 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 August 7, 2015, Chen, Tao; Foo, Thomas Jian Yao; Yeung, Ying-Yeung published an article.Reference of Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Indole-Catalyzed Bromolactonization in Lipophilic Solvent: A Solid-Liquid Phase Transfer Approach. And the article contained the following:

We have developed a novel indole-catalyzed bromolactonization of olefinic acids. The reaction could be conducted in lipophilic solvent through a solid-liquid phase transfer mechanism. This catalytic protocol has been applied to the synthesis of base-sensitive bromolactones. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Reference of Methyl 2-methyl-1H-indole-3-carboxylate

The Article related to olefinic acid indole bromolactonization catalyst solid liquid phase transfer, bromolactone preparation, General Organic Chemistry: Synthetic Methods and other aspects.Reference 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 August 15, 2013, Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Dakin, Les A.; Duplessis, Martin; Gehling, Victor S.; Harmange, Jean-Christophe; Naveschuk, Christopher G.; Vaswani, Rishi G. published a patent.Synthetic Route of 65417-22-3 The title of the patent was Preparation of heteroaryl amides as modulators of methyl modifying enzymes. And the patent contained the following:

The title compounds I [Z = CR2 or N; X1, X2 = N, CR3; X3 = N, CR6; no more than one of X1-X3 = N; R1, R2 = H, halo, OH, CN, etc.; or R1 and R2 are taken together with atoms to which they are bound to form (hetero)aryl, heterocyclyl, cycloalkyl; R3, R6 = H, halo, CN, etc.; or two R3 are taken together with atoms to which they are bound to form (hetero)aryl, heterocyclyl, cycloalkyl; R = (hetero)aryl, heterocyclyl, cycloalkyl, etc.], useful as agents for modulating Me modifying enzymes, were prepared Thus, reacting 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one with 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid afforded 26% II. Exemplified compounds I were tested against EZH2 and Y641N EZH2 mutant enzymes (data given for representative compounds I). Pharmaceutical composition comprising I is disclosed. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Synthetic Route of 65417-22-3

The Article related to heteroaryl amide preparation methyl modifying enzyme modulator antitumor, mutant ezh2 protein cancer treatment heteroaryl amide preparation, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Synthetic Route 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 August 18, 2016, Albrecht, Brian K.; Gehling, Victor C.; Harmange, Jean-Christophe; Vaswani, Rishi G. published a patent.Category: indole-building-block The title of the patent was Preparation of substituted indolecarboxamides as modulators of methyl modifying enzymes. And the patent contained the following:

The title compounds I [R1 = alkyl, alkoxy, or OCHF2; R2 = H, Me, Et, thiazolyl, etc.; R3, R31, R4, R41 = H, CF3, Me, Et, etc. (provided that at least one of R3, R31, R4 and R41 is not H); or R3 and R4 or R31 and R41 are taken together form a Ph or cyclohexyl ring], useful for treating a variety of diseases, disorders or conditions associated with Me modifying enzymes, notably EZH1 and EZH2, were prepared E.g., a multi-step synthesis of II, starting from Me 2-methyl-1-[1-(1-methyl-2-oxopiperidin-4- yl)ethyl]-1H-indole-3-carboxylate, was described. Exemplified compounds I were tested for their EZH2 activity (data given). Also provided are pharmaceutical compositions comprising compounds I, pharmaceutically acceptable salts thereof, and methods for their use in treating one or more diseases, disorders or conditions, associated with Me modifying enzymes, such as cancer. 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 indolecarboxamide pyridinylmethyl preparation modulator methyl modifying enzyme ezh1 ezh2, antitumor indolecarboxamide pyridinylmethyl preparation ezh1 ezh2 modulator, Heterocyclic Compounds (One Hetero Atom): Pyridines 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 August 15, 2013, Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Dakin, Les A.; Duplessis, Martin; Gehling, Victor S.; Harmange, Jean-Christophe; Naveschuk, Christopher G.; Vaswani, Rishi G. published a patent.Synthetic Route of 65417-22-3 The title of the patent was Preparation of heteroaryl amides as modulators of methyl modifying enzymes. And the patent contained the following:

The title compounds I [Z = CR2 or N; X1, X2 = N, CR3; X3 = N, CR6; no more than one of X1-X3 = N; R1, R2 = H, halo, OH, CN, etc.; or R1 and R2 are taken together with atoms to which they are bound to form (hetero)aryl, heterocyclyl, cycloalkyl; R3, R6 = H, halo, CN, etc.; or two R3 are taken together with atoms to which they are bound to form (hetero)aryl, heterocyclyl, cycloalkyl; R = (hetero)aryl, heterocyclyl, cycloalkyl, etc.], useful as agents for modulating Me modifying enzymes, were prepared Thus, reacting 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one with 5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid afforded 26% II. Exemplified compounds I were tested against EZH2 and Y641N EZH2 mutant enzymes (data given for representative compounds I). Pharmaceutical composition comprising I is disclosed. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Synthetic Route of 65417-22-3

The Article related to heteroaryl amide preparation methyl modifying enzyme modulator antitumor, mutant ezh2 protein cancer treatment heteroaryl amide preparation, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Synthetic Route 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 August 18, 2016, Albrecht, Brian K.; Gehling, Victor C.; Harmange, Jean-Christophe; Vaswani, Rishi G. published a patent.Category: indole-building-block The title of the patent was Preparation of substituted indolecarboxamides as modulators of methyl modifying enzymes. And the patent contained the following:

The title compounds I [R1 = alkyl, alkoxy, or OCHF2; R2 = H, Me, Et, thiazolyl, etc.; R3, R31, R4, R41 = H, CF3, Me, Et, etc. (provided that at least one of R3, R31, R4 and R41 is not H); or R3 and R4 or R31 and R41 are taken together form a Ph or cyclohexyl ring], useful for treating a variety of diseases, disorders or conditions associated with Me modifying enzymes, notably EZH1 and EZH2, were prepared E.g., a multi-step synthesis of II, starting from Me 2-methyl-1-[1-(1-methyl-2-oxopiperidin-4- yl)ethyl]-1H-indole-3-carboxylate, was described. Exemplified compounds I were tested for their EZH2 activity (data given). Also provided are pharmaceutical compositions comprising compounds I, pharmaceutically acceptable salts thereof, and methods for their use in treating one or more diseases, disorders or conditions, associated with Me modifying enzymes, such as cancer. 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 indolecarboxamide pyridinylmethyl preparation modulator methyl modifying enzyme ezh1 ezh2, antitumor indolecarboxamide pyridinylmethyl preparation ezh1 ezh2 modulator, Heterocyclic Compounds (One Hetero Atom): Pyridines 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 August 31, 1979, Kaneko, Chikara; Naito, Toshihiko; Hashiba, Marimi; Fujii, Harue; Somei, Masanori published an article.HPLC of Formula: 65417-22-3 The title of the article was Studies on the N-oxides of π-deficient N-heteroaromatics. Part XXXIII. A novel synthesis of revenine and related alkaloids by means of a photo-rearrangement reaction of 4-alkoxy-2-methylquinoline 1-oxides. And the article contained the following:

Photochem. rearrangement of methylquinoline oxides I (R = Me, allyl, Me2C:CHCH2, HCCCH2) in MeOH gave quinolinones II (R1 = H, R2 = Me; R1 = Me, R2 = H) and methoxyquinolinones III. II (R = Me2C:CHCH2, R1 = Me) is the alkaloid revenine from Rutaccous plants. Chlorination of 2-methyl-4-nitroquinoline oxide by concentrated HCl gave ∼80% 4-chloro-2-methylquinoline oxide, which was treated with ROH containing KOH to give ∼80% I. Photolysis of 4-(methoxycarbonyl)-2-methylquinoline oxide in MeOH gave 25.2% Me indole-3-carboxylate, 15.7% 4-(methoxycarbonyl)-3-methylcarbostyril, 12.3% Me 1-(1,1-dimethoxyethyl)indole-3-carboxylate, 11.5% Me 2-methylindole-3-carboxylate, and 4.3% 4-(methoxycarbonyl)-1-methylcarbostyril. The mechanism of the photorearrangement was discussed. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).HPLC of Formula: 65417-22-3

The Article related to revenine, alkenyloxyquinolone, rearrangement photochem alkoxyquinoline oxide, Alkaloids: Alkaloids Containing One Nitrogen Atom In A Ring and other aspects.HPLC of Formula: 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