Category: 642494-36-8

Qiu, Di published the artcileDirect synthesis of arylboronic pinacol esters from arylamines, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Organic Chemistry Frontiers (2014), 1(4), 422-425, database is CAplus.

A metal-free synthetic method based on Sandmeyer-type transformation for preparation of arylboronic pinacol esters from easily available aromatic amines as starting materials was described. This novel transformation affords borylation products in good yields under mild reaction conditions. This strategy can be easily carried out in gram-scale, demonstrating the practical usefulness of the method. Moreover, the Sandmeyer-type transformation can be followed by Suzuki-Miyaura cross-coupling reaction without purification of the arylboronate products.

Organic Chemistry Frontiers published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wu, Cheng-Jun published the artcileDesign, synthesis and biological evaluation of indole-based [1,2,4]triazolo[4,3-a] pyridine derivatives as novel microtubule polymerization inhibitors, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is European Journal of Medicinal Chemistry (2021), 113629, database is CAplus and MEDLINE.

A series of indole-based [1,2,4]triazolo [4,3-a]pyridine derivatives was designed and synthesized as novel microtubulin polymerization inhibitors by using a conformational restriction strategy. These compounds exhibited moderate to potent anti-proliferative activities against a panel of cancer cell lines (HeLa, A549, MCF-7 and HCT116). Among them, compound I featuring a N-methyl-5-indolyl substituent at the C-6 position of the [1,2,4]triazolo [4,3-a]pyridine core exhibited the highest antiproliferative activity with the IC₅₀ values ranging from 15 to 69 nM, and remarkable inhibitory effect on tubulin polymerization with an IC₅₀ value of 1.64μM. Mechanistic studies revealed that compound I induced cellular apoptosis and cell cycle arrest at the G₂/M phase in a dose-dependent fashion. Moreover, compound I significantly suppressed wound closure and disturbed microtubule networks.

European Journal of Medicinal Chemistry published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H10O4, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Prieto, Monica published the artcileArylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles. Partner role swapping and heterocycle protection, HPLC of Formula: 642494-36-8, the publication is Journal of Organic Chemistry (2004), 69(20), 6812-6820, database is CAplus and MEDLINE.

Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with Ph bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl, e.g., I. Furthermore, irresp. of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups were essential to ensuring optimum results in these Suzuki couplings.

Journal of Organic Chemistry published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, HPLC of Formula: 642494-36-8.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Appukkuttan, Prasad published the artcileMicrowave enhanced formation of electron rich arylboronates, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Synlett (2003), 1204-1206, database is CAplus.

Microwave assisted synthesis of electron rich aminoaryl- and indolylboronates via palladium-catalyzed boronation of the corresponding aryl bromides with bis(pinacolato)diboron are described. Reaction of bis(pinacolato)diboron with 1-bromo-2-R-4-R¹-benzene catalyzed by Pd(dppf)Cl₂ gave under microwave irradiation 2-(2-R-4-R¹-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes (2a–c, R, R¹: H, NMe₂;, H, NH₂;, NH₂, H). Similar reaction of bromo-1H-indoles XC₈H₆N (5a–d, X = 4-Br, 5-Br, 6-Br, 7-Br) gave the corresponding indolyldioxaborolanes (6a–d). Borylation of tris(4-bromophenyl)amine (3) gave tris[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (4). Compared to conventional heating conditions, dramatic rate enhancements were found for reactions carried out under microwave irradiation, reducing reaction times from hours or days to only minutes.

Synlett published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

de Lucas, Ana I. published the artcileScaffold Hopping to Imidazo[1,2-a]pyrazin-8-one Positive Allosteric Modulators of Metabotropic Glutamate 2 Receptor, HPLC of Formula: 642494-36-8, the publication is ACS Omega (2021), 6(35), 22997-23006, database is CAplus and MEDLINE.

Glutamate hyperfunction is implicated in multiple neurol. and psychiatric diseases. Activation of the mGlu2 receptor results in reduced glutamate release and decreased excitability representing a promising novel therapeutic agent for the treatment of disorders such as epilepsy, schizophrenia, mood, anxiety, and other neuropsychiatric disorders. We have previously reported substantial efforts leading to potent and selective mGlu2 PAMs from different chem. series. Herein, the discovery and optimization of a novel series of imidazopyrazinone mGlu2 PAMs are reported. This new scaffold originated from computational searching of fragment databases and comparison with our previously explored scaffolds. Optimization guided by our robust understanding of SAR from former series led to potent, selective, and brain-penetrant compounds

ACS Omega published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, HPLC of Formula: 642494-36-8.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lim, Soobin published the artcileCobalt-Catalyzed C-F Bond Borylation of Aryl Fluorides, Product Details of C14H18BNO2, the publication is Organic Letters (2018), 20(22), 7249-7252, database is CAplus and MEDLINE.

A mild and practical Co-catalyzed defluoroborylation of fluoroarenes is presented for the 1st time. The method permits straightforward functionalization of fluoroarenes, with high selectivity for borylation of C-F over C-H bonds, and a tolerance for aerobic conditions. Also, two-step ¹⁸F-fluorination was achieved for expanding the scope of ¹⁸F-positron emission tomog. probes.

Organic Letters published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Product Details of C14H18BNO2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Londregan, Allyn T. published the artcileSynthesis of Pyridazine-Based α-Helix Mimetics, Recommanded Product: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is ACS Combinatorial Science (2016), 18(10), 651-654, database is CAplus and MEDLINE.

A versatile synthesis of pyridazine-based small mol. α-helix mimetics is presented. Modular C-C, C-N, and C-O bond-forming reactions allow for the inclusion of a variety of aliphatic, basic, aromatic, and heteroaromatic side chain moieties. This robust synthesis is suitable for the preparation of small pyridazine-based libraries.

ACS Combinatorial Science published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Recommanded Product: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Londregan, Allyn T. published the artcileSynthesis of Pyridazine-Based α-Helix Mimetics, Recommanded Product: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is ACS Combinatorial Science (2016), 18(10), 651-654, database is CAplus and MEDLINE.

A versatile synthesis of pyridazine-based small mol. α-helix mimetics is presented. Modular C-C, C-N, and C-O bond-forming reactions allow for the inclusion of a variety of aliphatic, basic, aromatic, and heteroaromatic side chain moieties. This robust synthesis is suitable for the preparation of small pyridazine-based libraries.

ACS Combinatorial Science published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Recommanded Product: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Huang, Shenlin published the artcileSynthesis and biological study of 2-amino-4-aryl-5-chloropyrimidine analogues as inhibitors of VEGFR-2 and cyclin dependent kinase 1 (CDK1), Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(8), 2179-2183, database is CAplus and MEDLINE.

The series of 2-amino-4-aryl-5-chloropyrimidines, e.g., I, was discovered to be potent for both VEGFR-2 and CDK1. Described here are the chem. for analog synthesis, SAR study, and its kinase selectivity profiling. The full rat PK data and in vivo efficacy study are also included.

Bioorganic & Medicinal Chemistry Letters published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zischler, Johannes published the artcileAlcohol-Enhanced Cu-Mediated Radiofluorination, COA of Formula: C14H18BNO2, the publication is Chemistry – A European Journal (2017), 23(14), 3251-3256, database is CAplus and MEDLINE.

The potential of many ¹⁸F-labeled (hetero)aromatics for applications in positron emission tomog. remains underexplored because convenient procedures for their radiosynthesis are lacking. Consequently, simple methods to prepare radiofluorinated (hetero)arenes are highly sought after. Herein, we report the beneficial effect of primary and secondary alcs. on Cu-mediated ¹⁸F-labeling. This observation contradicts the assumption that such alcs. are inappropriate solvents for aromatic fluorination. Therefore, we developed a protocol for rapid radiolabeling of an extraordinarily broad scope of boronic and stannyl substrates under general reaction conditions. Notably, radiofluorinated indoles, phenols, and anilines were synthesized directly from the corresponding unprotected precursors. Furthermore, the novel method enabled the preparation of radiofluorinated tryptophans, [¹⁸F]F-DPA, [¹⁸F]DAA1106, 6-[¹⁸F]FDA, and 6-[¹⁸F]FDOPA.

Chemistry – A European Journal published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C9H16BNO2, COA of Formula: C14H18BNO2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles