Tag: M.W=250-300

Scott, Colleen N.; Wilcox, Craig S. published the artcile< A Mild Synthesis of Unsymmetrical Bisalkoxysilanes through Catalyzed Alcoholysis of Hydridosilanes Containing C-C Multiple Bonds and Aryl Halides>, Computed Properties of 1013031-65-6, the main research area is silane bis alkoxy preparation; alcoholysis hydrido silane manganese catalyst alkenol aryl bromide.

The synthesis of unsym. bisalkoxysilanes containing unsaturated C-C bonds and alkyl and aryl bromides has been developed. This method is a modification of our previously reported two-step procedure that utilizes readily available catalysts (rhodium acetate dimer and manganese pentacarbonyl bromide) under mild neutral aprotic conditions. Good to moderate yields of the products were obtained in a short period. In this two-step synthesis, unsym. bisalkoxysilanes with groups that can be further functionalized can be prepared effectively without the need to isolate the intermediates.

Journal of Organic Chemistry published new progress about Alcoholysis. 1013031-65-6 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6Br2O, Computed Properties of 1013031-65-6.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ge, Shaozhong; Arlow, Sophie I.; Mormino, Michael G.; Hartwig, John F. published the artcile< Pd-Catalyzed α-Arylation of Trimethylsilyl Enolates of α,α-Difluoroacetamides>, Product Details of C12H16BrNO2, the main research area is difluorotrimethylsilylacetamide aryl heteroaryl bromide arylation palladium catalyst; aryl difluoroketone difluoroacetaldehyde difluoroacetate difluoroethanol difluoroethylamine preparation; difluoroethanol ethylamine preparation.

We report the arylation and heteroarylation of α,α-difluoro-α-(trimethylsilyl)acetamides with aryl and heteroaryl bromides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)2Cy as ligand. A broad range of electronically varied aryl and heteroaryl bromides underwent this transformation to afford α-aryl-α,α-difluoroacetamides in high yields. Due to the electrophilicity of the fluorinated amide, this palladium-catalyzed cross-coupling reaction provides a versatile platform to generate a range of α,α-difluoro carbonyl compounds, such as α-aryl-α,α-difluoroketones, -acetaldehydes, -acetates, and acetic acids, and difluoroalkyl derivatives, such as 2-aryl-2,2-difluoroethanols and -ethylamines, under mild conditions.

Journal of the American Chemical Society published new progress about Acetamides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (difluoro trimethylsilyl). 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Product Details of C12H16BrNO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Trammel, Grace L.; Kuniyil, Rositha; Crook, Phillip F.; Liu, Peng; Brown, M. Kevin published the artcile< Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines>, Electric Literature of 639520-70-0, the main research area is indole derivative preparation nickel catalyzed dearomative arylboration diborane; borylated arylindoline asym preparation; potential energy surface dearomative arylboration indole derivative; azamedicarpin natural product multistep enantioselective preparation.

Indole dearomatization is an important strategy to access indolines: a motif present in a variety of natural products and biol. active mols. Herein, a method for transition-metal catalyzed regioselective dearomative arylboration of indoles to generate diverse indolines is presented. The method accomplishes intermol. dearomatization of simple indoles through a migratory insertion pathway on substrates that lack activating or directing groups on the C2- or C3-positions. Synthetically useful C2- and C3-borylated indolines can be accessed through a simple change in N-protecting group in high regio- and diastereoselectivities (up to >40:1 rr and >40:1 dr) from readily available starting materials. Addnl., the origin of regioselectivity was explored exptl. and computationally to uncover the remarkable interplay between carbonyl orientation of the N-protecting group on indole, electronics of the C2-C3 π-bond, and sterics. The method enabled the 1st enantioselective synthesis of (-)-azamedicarpin.

Journal of the American Chemical Society published new progress about Borylation. 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Electric Literature of 639520-70-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Shi, Hang; Braun, Augustin; Wang, Lu; Liang, Steven H.; Vasdev, Neil; Ritter, Tobias published the artcile< Synthesis of 18F-Difluoromethylarenes from Aryl (Pseudo) Halides>, Recommanded Product: tert-Butyl (4-bromophenyl)(methyl)carbamate, the main research area is fluoromethyl arene 18F labeled chemoselective preparation; fluoroacetophenone chemoselective preparation bromination fluorination deacylation; coupling aryl halide pseudohalide fluoroacetophenone bromination substitution fluoride deacylation; bromination substitution 18F fluoride deacylation arylfluoromethyl phenyl ketone; aryl (pseudo) halides; difluoromethylarenes; fluorine-18; positron emission tomography; radiopharmaceuticals.

A general, operationally simple, and chemoselective method for the synthesis of [18F]difluoromethylarenes such as I (R = 18FFCH) from [18F]fluoride and aryl chlorides, bromides, iodides, and triflates or pseudohalides such as I (R = TfO) is reported. Coupling of the aryl halides or pseudohalides to α-fluoroacetophenone in the presence of a palladium biphenylamine precatalyst yields α-fluoro-α-arylmethyl Ph ketones such as I (R = PhCOCHF); α-bromination and substitution with [18F]fluoride, tetraethylammonium bromide, and N-bromophthalimide in acetonitrile and chlorobenzene followed by deacylation with aqueous KOH yielded mono-[18F]-labeled difluoromethylarenes such as I (R = 18FFCH) in 10-60% radiochem. yields. The method was used to prepared 18F-difluoromethylated analogs of pharmaceuticals such as Claritin, fluoxetine (Prozac), and DAA1106.

Angewandte Chemie, International Edition published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Recommanded Product: tert-Butyl (4-bromophenyl)(methyl)carbamate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Gao, Pin; Chen, Liang-An; Brown, M. Kevin published the artcile< Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes>, Safety of tert-Butyl (4-bromophenyl)(methyl)carbamate, the main research area is aryl bromide arylboron reagent alkenylarene nickel diarylation catalyst; alkane aryl stereoselective preparation.

A three-component coupling of aryl bromides, arylboron reagents, and alkenylarenes is presented. The method tolerates a variety of substitution patterns on all of the components. In particular, 1,2-disubstituted alkenylarenes are suitable and undergo highly diastereoselective diarylation.

Journal of the American Chemical Society published new progress about Alkylarenes Role: SPN (Synthetic Preparation), PREP (Preparation). 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Safety of tert-Butyl (4-bromophenyl)(methyl)carbamate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mfuh, Adelphe M.; Doyle, John D.; Chhetri, Bhuwan; Arman, Hadi D.; Larionov, Oleg V. published the artcile< Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts>, Related Products of 2252-45-1, the main research area is photoinduced borylation haloarene hydroxydiboron agent; boronic acid ester aryl preparation; cyanophenyl boronic acid preparation crystal structure; mol structure cyanophenyl boronic acid; aryl ammonium salt photoinduced borylation hydroxydiboron agent.

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

Journal of the American Chemical Society published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent) (haloarenes). 2252-45-1 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3S, Related Products of 2252-45-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Bunnett, J. F.; Rauhut, Michael M.; Knutson, David; Bussell, Geo. E. published the artcile< The conditions, scope, and mechanism of the von Richter reaction>, Recommanded Product: 2,3-Dibromobenzoic acid, the main research area is .

Experiments with D compounds showed that in the reaction of p-O2NC6H4Cl (I) with alc. KCN to form m-ClC6H4CO2H (II), and in the transformation of PhNO2 to BzOH, H exchange with the solvent occurred. Efforts to isolate a nitrile intermediate have been unsuccessful, but it is shown that nitriles are hydrolyzed rapidly under the conditions of the reaction. Br2C6H3NO2 (III) having Br ortho to the NO2 group reacted poorly, but III with unflanked NO2 groups gave fair yields. A tarry, amorphous byproduct was shown to contain CO2H groups. The optimum conditions for the reaction have been defined and the mechanism is discussed. 2,6-Br2C6H3NH2 diazotized in 9.5M HCl below 0°, and the diazonium cobaltinitrite prepared and decomposed by the method of Hodgson and Marsden (C.A. 38, 2021.8) gave 22% 2,6-III m. 81-3°. m-BrC6H4NHAc nitrated by the method of Case and Sloviter (C.A. 32, 529.9), the resulting mixed products deacetylated by acid hydrolysis, the crude mixed anilines diazotized, and the diazonium salts treated with CuBr gave 2,4-III. 3,5-III, m. 105-6°, was prepared by the method of Shepherd (C.A. 41, 4465h). The nitration of p-C6H4Br2, m. 87°, gave 2,5-III, m. 81-3°. Heating 12.5 g. p-ClC6H4NH2.HCl and 10 g. 99.5% D2O 112 h. at 120° in a sealed tube (or 24 h. at 150°), neutralizing with 6M NaOH, diluting with about 40 cc. dioxane, adding the solution slowly with stirring to a previously prepared mixture of 43 cc. cold concentrated H2SO4 and 50 g. K2S2O8, stirring 1 h. with cooling, pouring onto 300 cc. crushed ice, neutralizing with saturated aqueous Na2CO3, filtering off the light yellow, flocculent material, letting the mixture stand, filtering off a 2nd crop after 1.5 h., dissolving the combined material in 200 cc. glacial AcOH, treating the solution with 200 cc. 30% H2O2, 200 cc. glacial AcOH, and 13 g. HNO3 (d. 1.42), heating the resulting green solution 45 min. on the steam bath, pouring it into 1500 cc. H2O, and recrystallizing the flocculent precipitate from EtOH yielded 6.2 g. D-labeled I (IV), m. 81.5-2.5°, containing 1.02 atoms D/mol. In another run the contents of the sealed tube treated with dilute HCl, diazotized, the diazonium cobaltinitride formed and decomposed in the usual manner, and the product steam distilled and recrystallized from EtOH gave 2.6 g. IV, m. 83-4°, containing 0.99 atom D/mol. B(OEt)3 (10.8 g.) and 5.0 g. D2O kept overnight, and the mixture distilled gave EtOD which was stored in sealed ampuls. A series of von Richter reactions [cf. Ber. 8, 1418(1875)] was carried out by the procedure described previously (C.A. 44, 9938c) with 4.0 g. p-BrC6H4NO2 (V) each under the following conditions (time in hrs., weight of KCN used in g., aqueous solvent, % conversion, and % recovered V given). At 150° in a sealed tube: 1, 2.6, 25 cc. 50% MeOH, 12.5, 55; 1, 10.4, 25 cc. 50% MeOH, 21, 0; 1, 2.6, 25 cc. 48% EtOH, 22, 35; 1, 2.6, 25 cc. 50% PrOH, 11, 55; 1, 2.6, 25 cc. 50% iso-PrOH, 10, 72; 1, 2.6, 25 cc. 50% BuOH, 2.5, 85. At reflux temperature: 48, 8.1, 34 cc. 48% EtOH, 37, 0; 1.5, 15.0, 50 g. 95% pinacol, 1.5, 60; 2.5, 15.0, 75 cc. (HOCH2CH2)2O, 2.5, 0; 2.5, 15.0, 30 cc. 99% BuC(OH)Me2, 0, 65; 2.5, 15.0, 98% AmC(OH)MeBu, 0, 70. PhNO2 (2.5 g.) in 25 cc. 75% aqueous pyridine heated with 2.6 g. KCN 1 h. in a sealed tube at 150° gave only 96% recovered PhNO2. In a similar run in 25 cc. 80% dioxane with 5.0 g. KCN in a sealed tube during 2 h. at 160°, 88% PhNO2 was recovered. PhNO2 (2.5 g.) and 5.0 g. KCN in 25 cc. 48% aqueous EtOH heated 1.5 h. in a sealed tube at 160° yielded 10% BzOH and 12% recovered PhNO2. A series of similar runs was carried out with I (time, weight of I used in g., weight of KCN, aqueous solvent, % conversion, and % recovered I given): Sealed tube at 150°: 50 min. 2.5, 5.0, 25 cc. 48% EtOH, 38, 0. Reflux: 48 h. 3.15, 200.0, 600 cc. 48% EtOH, 42, 0; 18 h. 3.15, 10.3, 75 cc. 48% EtOH, 20, 19; 48 h., 3.15, 20.0, 75 cc. 95% EtOH, 14, 33; 48 h., 3.00, 6.45, 26 cc. 48% EtOH, 40, 0; 48 h., 3.15, 20, 75 cc. 50% MeOH, 20, 0; 48 h., 3.15, 20, 75 cc. 33% MeOH, 15, 6; 48, 3.15, 20, 75 cc. 50% iso-PrOH, 9, 47; 20 h., 3.15, 10.3, 90 cc. 53% EtOH and 22% C6H6, 0, 61; 45 h., 3.15, 20, 75 cc. 50% MeCN, 0, -. Sealed tube at 150°: 1 h., 3.15, 2.6, 75 cc. 50% glycerol-25% EtOH, 0, 79; 1 h., 3.15, 2.6, 75 cc. 50% dioxane, 7, 56. A number of aromatic nitro compounds was submitted to the von Richter reaction; the nitro compound used, the products obtained, % conversion, and % recovered starting material are given for the following reactions in a sealed tube: p-O2NC6H4I, m-IC6H4CO2H (m. 182-3°), 40, 0; 3,5-Cl2C6H3NO2 (m. 63.8-4.2°), 2,4-Cl2C6H3CO2H (m. 158.5-9.5°), 30, 0; m-O2NC6H4F, no acid, 0, 74; p-O2NC6H4F (m. 57-9°), no acid, 0, 14 (the recovered starting material was converted to p-FC6H4CONHPh, m. 182-4°, for identification); p-C6H4(NO2)2, no acid, 0, 6; 2,3-III (m. 85°), 3,4-Br2C6H3CO2H (m. 225-7°), 1, 0 (at reflux); 3,4-III (m. 56-8°), 2,3-Br2C6H3CO2H (m. 144-8°), 16, 0; 2,6-III, no acid, 0, 93; 2,4-III, 3,5-Br2C6H3CO2H (m. 219-20°), 2, 0 (amide, m. 184-6°) (reflux); 3,5-III, 2,4-Br2C6H3CO2H (m. 163-9°), 18, 32 (amide, m. 195-6°); 2,5-III, 2,5-Br2C6H3CO2H (m. 151-3°), 7, 23; 2-O2NC6H4Br, m-BrC6H4CO2H (m. 151-3°), 2, 44 (reflux). PhNO heated 1 h. at 155° with 2.6 g. KCN in 25 cc. 48% EtOH yielded 0.3 g. (PhN:)2, m. 65-6°, which was reduced with Sn and HCl to benzidine, m. 117-20°; in similar runs in 75% dioxane, azoxybenzene, m. 29-31°, was obtained. PhNO2 (5.0 g.), 5.0 g. anhydrous KCN, 5 cc. EtOD, and 5 cc. D2O heated 1 h. in a sealed tube at 150-60° gave 3 g. PhNO2 and 0.380 g. BzOH, m. 120.5-21° (from H2O); the BzOH obtained contained, after equilibration of its CO2H H atoms with H2O, 0.72 atom D/mol. The recovered PhNO2 was nearly D-free. Thus, H atoms from the solvent do become attached to aromatic C during the von Richter reaction. IV (2.2 g.) (containing 1.02 atom D/mol.), 5 g. KCN, and 30 cc. 48% EtOH heated 75 min. at 160-70° in a sealed tube gave II containing 0.42 atom D/mol. IV (containing 0.99 atom D/mol.) gave similarly II containing 0.38 atom D/mol.

Journal of the American Chemical Society published new progress about Intermediates. 603-78-1 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4Br2O2, Recommanded Product: 2,3-Dibromobenzoic acid.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Abram, Michal; Rapacz, Anna; Mogilski, Szczepan; Latacz, Gniewomir; Lubelska, Annamaria; Kaminski, Rafal M.; Kaminski, Krzysztof published the artcile< Multitargeted Compounds Derived from (2,5-Dioxopyrrolidin-1-yl)(phenyl)-Acetamides as Candidates for Effective Anticonvulsant and Antinociceptive Agents>, Recommanded Product: (3-Bromophenyl)(trifluoromethyl)sulfane, the main research area is epilepsy neuropathic pain anticonvulsant antinociceptive multitargeted drugs hybrid compound; Hybrid compounds; anticonvulsant activity; antinociceptive activity; epilepsy; multitargeted drugs; neuropathic pain.

We developed a focused set of original hybrid pyrrolidine-2,5-dione derivatives with potent anticonvulsant and antinociceptive properties. These hybrid compounds demonstrated broad-spectrum protective activity in a range of mouse models, such as the maximal electroshock (MES) test, the pentylenetetrazole-induced seizures (scPTZ), and the 6 Hz (32 mA) seizures. Compound 22(I) showed the most potent anticonvulsant activity (ED50 MES = 23.7 mg/kg, ED50 6 Hz (32 mA) = 22.4 mg/kg, ED50scPTZ = 59.4 mg/kg). In addition, 22 revealed potent efficacy in the formalin-induced tonic pain. These in vivo activities of 22 are likely mediated by several targets and may result from the inhibition of central sodium/calcium currents and transient receptor potential vanilloid 1 (TRPV1) receptor antagonism. Finally, the lead compound 22 revealed drug-like absorption, distribution, metabolism, excretion, toxicity (ADME-Tox) properties in the in vitro assays, making it a potential candidate for further development in epilepsy and neuropathic pain indications.

ACS Chemical Neuroscience published new progress about Analgesics. 2252-45-1 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3S, Recommanded Product: (3-Bromophenyl)(trifluoromethyl)sulfane.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Vechorkin, Oleg; Godinat, Aurelien; Scopelliti, Rosario; Hu, Xile published the artcile< Cross-Coupling of Nonactivated Alkyl Halides with Alkynyl Grignard Reagents: A Nickel Pincer Complex as the Catalyst>, Application In Synthesis of 639520-70-0, the main research area is alkyl halide alkynyl Grignard cross coupling nickel catalysis.

Alkynes containing nonactivated alkyl groups, especially those with β-hydrogen atoms, are difficult to synthesize. In this paper, we have disclosed the first general nickel-catalyzed cross-coupling of nonactivated alkyl halides with alkynyl Grignard reagents. The wide scope and high functional group tolerance makes the method attractive for the streamlined preparation of alkynes containing nonactivated alkyl groups. At this moment, only primary alkyl halides can be coupled. Methods to couple secondary alkyl halides are currently being developed in our laboratory

Angewandte Chemie, International Edition published new progress about Cross-coupling reaction. 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Application In Synthesis of 639520-70-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Cao, Qingxiang; Luo, Jie; Zhao, Xiaodan published the artcile< Chiral Sulfide Catalysis for Desymmetrizing Enantioselective Chlorination>, Recommanded Product: (2,6-Dibromophenyl)methanol, the main research area is chiral sulfide catalyzed desymmetrizing enantioselective chlorination aryl olefin; tetralin enantioselective diastereoselective synthesis; tricyclic hexahydrophenalene enantioselective diastereoselective synthesis; spiro nitrogen heterocycle synthesis; Lewis base catalysis; chlorination; cyclizations; olefins; synthetic methods.

An unprecedented chiral sulfide catalyzed desymmetrizing enantioselective chlorination is disclosed. Various aryl-tethered diolefins and diaryl-tethered olefins afforded tetralins and tricyclic hexahydrophenalene derivatives, resp., bearing multiple stereogenic centers in high yields with excellent enantio- and diastereoselectivities [e.g., I → II (91%, 93% ee, 31:1 d.r.) in presence of sulfide III, DCDMH as Cl+ reagent and Tf2NH as acid in CH2Cl2]. In contrast, the tertiary amine catalyst (DHQD)2PHAL led to a diastereomeric product. The products could be transformed into a variety of compounds, such as spiro-N-heterocycles.

Angewandte Chemie, International Edition published new progress about Alkadienes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (aryl-tethered diolefins). 1013031-65-6 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6Br2O, Recommanded Product: (2,6-Dibromophenyl)methanol.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary