Tag: 200-300

Faraggi, Tomer M.; Rouget-Virbel, Caroline; Rincon, Juan A.; Barberis, Mario; Mateos, Carlos; Garcia-Cerrada, Susana; Agejas, Javier; de Frutos, Oscar; MacMillan, David W. C. published their research in Organic Process Research & Development in 2021. The article was titled 《Synthesis of enantiopure unnatural amino acids by metallaphotoredox catalysis》.Category: nitriles-buliding-blocks The article contains the following contents:

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogs of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technol. The experimental part of the paper was very detailed, including the reaction process of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Category: nitriles-buliding-blocks 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic Process Research & Development included an article by Remarchuk, Travis; Angelaud, Remy; Askin, David; Kumar, Archana; Thompson, Andrew S.; Cheng, Hua; Reichwein, John F.; Chen, Yanping; St-Jean, Frederic. Reference of 4-Bromo-2-fluorobenzonitrile. The article was titled 《Manufacture of the PI3K β-Sparing Inhibitor Taselisib. Part 1: Early-Stage Development Routes to the Bromobenzoxazepine Core》. The information in the text is summarized as follows:

Two convergent regioselective routes for the synthesis of the tetracyclic imidazobenzoxazepine triazole I, a key intermediate toward the synthesis of taselisib, are described. In the first-generation route, a chemoselective Negishi cross-coupling reaction was developed between iodoimidazole II and 1-isopropyl-3-methyl-1H-1,2,4-triazole, which enabled the delivery of initial kilogram quantities of I. Because of the inefficiencies in the preparation of the imidazole II, a second-generation route via a highly regioselective imidazole ring formation between α-chloroketone III and aryl amidine IV was developed. The resulting imidazole V provided the handle to efficiently install the seven-membered benzoxazepine ring system in one pot with two-step N-alkylation and SNAr tandem reactions. The experimental process involved the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Reference of 4-Bromo-2-fluorobenzonitrile)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Reference of 4-Bromo-2-fluorobenzonitrile 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Wang, Shao-Feng; Cao, Xiao-Ping; Li, Yang published 《Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis》.Angewandte Chemie, International Edition published the findings.Category: nitriles-buliding-blocks The information in the text is summarized as follows:

The authors have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C-O bond cleavage, the authors developed a novel approach to the C-O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a 1-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Category: nitriles-buliding-blocks 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

See, Cheng Shang; Kitagawa, Mayumi; Liao, Pei-Ju; Lee, Kyung Hee; Wong, Jasmine; Lee, Sang Hyun; Dymock, Brian W. published their research in European Journal of Medicinal Chemistry on August 5 ,2018. The article was titled 《Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)》.Application of 89245-35-2 The article contains the following contents:

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20mg/kg IP twice a day. After reading the article, we found that the author used 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Application of 89245-35-2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application of 89245-35-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

O’Hara, Fionn; Blackmond, Donna G.; Baran, Phil S. published their research in Journal of the American Chemical Society on August 14 ,2013. The article was titled 《Radical-Based Regioselective C-H Functionalization of Electron-Deficient Heteroarenes: Scope, Tunability, and Predictability》.Electric Literature of C7H2ClF3N2 The article contains the following contents:

Radical addition processes can be ideally suited for the direct functionalization of heteroaromatic bases, yet these processes are only sparsely used due to the perception of poor or unreliable control of regiochem. A systematic investigation of factors affecting the regiochem. of radical functionalization of heterocycles using alkylsulfinate salts revealed that certain types of substituents exert consistent and additive effects on the regioselectivity of substitution. This allowed us to establish guidelines for predicting regioselectivity on complex π-deficient heteroarenes, including pyridines, pyrimidines, pyridazines, and pyrazines. Since the relative contribution from opposing directing factors was dependent on solvent and pH, it was sometimes possible to tune the regiochem. to a desired result by modifying reaction conditions. This methodol. was applied to the direct, regioselective introduction of iso-Pr groups into complex, biol. active mols., such as diflufenican (I; R = H → R = iso-Pr) and nevirapine (II; R = H → R = iso-Pr). In the experimental materials used by the author, we found 6-Chloro-2-(trifluoromethyl)nicotinonitrile(cas: 1245913-20-5Electric Literature of C7H2ClF3N2)

6-Chloro-2-(trifluoromethyl)nicotinonitrile(cas: 1245913-20-5) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Electric Literature of C7H2ClF3N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Campbell, Mark W.; Yuan, Mingbin; Polites, Viktor C.; Gutierrez, Osvaldo; Molander, Gary A. published their research in Journal of the American Chemical Society in 2021. The article was titled 《Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization》.Formula: C7H3BrFN The article contains the following contents:

Herein, the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes was reported. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provided a new, more atom-economic outlook for organic synthesis. Through detailed exptl. and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered. In the experimental materials used by the author, we found 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Formula: C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Ionothermal synthesis of crystalline microporous aluminophosphates: Systematic study on the conditions affecting the framework type》 was written by Azim, Muhammad Mohsin; Pensado, Alfonso; Kirchner, Barbara; Gutmann, Torsten; Groszewicz, Pedro B.; Buntkowsky, Gerd; Stark, Annegret. Name: 4-Cyano-3-fluorophenyl 4-butylbenzoate And the article was included in Microporous and Mesoporous Materials on August 31 ,2018. The article conveys some information:

In a systematic study on the synthesis of aluminophosphates (AlPOs) under ionothermal conditions, initially using 1-butyl-3-methylimidazolium bromide ([C4mim]Br) as ionic liquid solvent and structure-directing agent, the effect of the reaction conditions (i.e. molar P/Al, F/Al and ionic liquid/Al ratios, alternative fluoride sources, influence of the ionic liquid’s cation or anion, temperature, reaction time) on the framework type was studied in detail. In [C4mim]Br, the formation of the more thermodynamically stable AEL framework type proceeds via AFI. The framework type can be changed by choosing another anion or cation of the ionic liquid Hence, the successful ionothermal synthesis of the AFI framework AlPO is reported by using either N-ethylpyridinium bromide ([C2py]Br) or 1-butyl-3-methylimidazolium chloride ([C4mim]Cl). The mineralizer [Me4N]F, rather than HF, has been used for the first time as an alternative fluoride source in ionothermal synthesis, which can also affect the framework type. Hence, a very efficient synthesis of the LTA framework type is reported in [C4mim]Br using [Me4N]F. Ab initio mol. dynamics (AIMD) studies showed that the anion bridges between the aluminum atoms of the framework and the cation. The interaction is more favored in the presence of the bromide than the chloride, which may be a clue to the question why the AEL framework is not formed in the chloride-based ionic liquid This study opens several routes to pursue in the future as numerous ionic liquids are available which can be used in ionothermal synthesis. In addition to this study using 4-Cyano-3-fluorophenyl 4-butylbenzoate, there are many other studies that have used 4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5Name: 4-Cyano-3-fluorophenyl 4-butylbenzoate) was used in this study.

4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Name: 4-Cyano-3-fluorophenyl 4-butylbenzoate

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Enantioselective H-bond-directing approach for trienamine-mediated reactions in asymmetric synthesis》 was published in Angewandte Chemie, International Edition in 2012. These research results belong to Albrecht, Lukasz; Cruz Acosta, Fabio; Fraile, Alberto; Albrecht, Anna; Christensen, Jannie; Jorgensen, Karl Anker. HPLC of Formula: 50743-32-3 The article mentions the following:

The first H-bond-directed trienamine-mediated [4+2] cycloaddition was developed, thereby demonstrating the viability of such an activation strategy. The reaction between diversely substituted 2,4-dienals and 3-cyanochromones proceeded smoothly and in a highly stereoselective manner in the presence of a squaramide-containing aminocatalyst. Furthermore, it was demonstrated that the obtained cycloadducts can be chemo- and diastereoselectively transformed into polycyclic products with high mol. and stereochem. complexity that possess up to five stereogenic centers. An unexpected stereochem. outcome of the reaction was observed and a rationalization of the results was provided. In the experimental materials used by the author, we found 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3HPLC of Formula: 50743-32-3)

6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.HPLC of Formula: 50743-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 105942-08-3In 2019 ,《Manufacture of the PI3K β-Sparing Inhibitor Taselisib. Part 2: Development of a Highly Efficient and Regioselective Late-Stage Process》 was published in Organic Process Research & Development. The article was written by St-Jean, Frederic; Remarchuk, Travis; Angelaud, Remy; Carrera, Diane E.; Beaudry, Danial; Malhotra, Sushant; McClory, Andrew; Kumar, Archana; Ohlenbusch, Gerd; Schuster, Andreas M.; Gosselin, Francis. The article contains the following contents:

A highly efficient and regioselective manufacturing route for the phosphoinositide 3-kinase β-sparing inhibitor taselisib (I) was developed. Highlights of the synthesis include: (1) magnesium-mediated formation of a challenging cyclic amidine; (2) regioselective imidazole construction via alkylation/condensation with bromopyruvic acid; and (3) triazole formation with 2-iso-Pr acetamidrazone to generate the key bromobenzoxazepine core intermediate. Subsequent highly efficient one-pot palladium-catalyzed Miyaura borylation/Suzuki cross-coupling/saponification, followed by a 1,1′-carbonyldiimidazole-mediated coupling with ammonia, led to the pentacyclic taselisib. This new synthetic approach provides a more efficient route to taselisib with a significant decrease in process mass intensity compared to the previous early development routes to the bromobenzoxazepine core. Finally, implementation of a controlled crystallization provided the active pharmaceutical ingredient with the desired polymorphic form.4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Related Products of 105942-08-3) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Related Products of 105942-08-3 It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

COA of Formula: C10H7BrN2On November 3, 1993 ,《Novel applications of vinylogous Mannich reactions. Total synthesis of rugulovasines A and B》 appeared in Journal of the American Chemical Society. The author of the article were Martin, Stephen F.; Liras, Spiros. The article conveys some information:

The total syntheses of the Ergot alkaloids rugulovasines A (I, R = MeNH, R1 = H) and B (R = H, R1 = MeNH) were completed in a concise sequence requiring only eight reactions from com. available 4-bromoindole. The two key steps of the synthesis were the vinylogous Mannich reaction of the iminium salt of II with the furan III and the cyclization of IV by a SRN1 reaction. Thus, 4-bromoindole was converted in a straightforward manner to the 3-acetaldehyde derivative, which after treatment with benzylmethylamine provided the intermediate enamine II. Treatment of II with silyloxyfuran III in the presence of acid produced IV via a vinylogous Mannich reaction. A photostimulated SRN1 reaction of IV was employed to construct the spirocyclic lactone moiety followed by hydrogenolysis gave rugulovasines A and B. The experimental process involved the reaction of 2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2COA of Formula: C10H7BrN2)

2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.COA of Formula: C10H7BrN2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts