Month: November 2022

《Reductive sp3-sp2 Coupling Reactions Enable Late-Stage Modification of Pharmaceuticals》 was published in Organic Letters in 2020. These research results belong to Mennie, Katrina M.; Vara, Brandon A.; Levi, Samuel M.. HPLC of Formula: 3395-91-3 The article mentions the following:

Late-stage derivatization of pharmaceutically relevant scaffolds relies on the availability of highly functional-group tolerant reactions. Reactions that increase the sp3 character of mols. enable the pursuit of more selective and well-tolerated pharmaceuticals. Herein, we report the use of sp3-sp2 cross-electrophile reductive couplings to modify a generic ATP-competitive kinase inhibitor with a broad range of primary and secondary alkyl halide coupling partners. After reading the article, we found that the author used Methyl 3-bromopropanoate(cas: 3395-91-3HPLC of Formula: 3395-91-3)

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents.HPLC of Formula: 3395-91-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Synergistic photoredox and copper catalysis by diode-like coordination polymer with twisted and polar copper-dye conjugation》 was published in Nature Communications in 2020. These research results belong to Shi, Yusheng; Zhang, Tiexin; Jiang, Xiao-Ming; Xu, Gang; He, Cheng; Duan, Chunying. Formula: C18H12Br3N The article mentions the following:

Synergistic photoredox and copper catalysis confers new synthetic possibilities in the pharmaceutical field, but is seriously affected by the consumptive fluorescence quenching of Cu(II). By decorating bulky auxiliaries into a photoreductive triphenylamine-based ligand to twist the conjugation between the triphenylamine-based ligand and the polar Cu(II)-carboxylate node in the coordination polymer, we report a heterogeneous approach to directly confront this inherent problem. The twisted and polar Cu(II)-dye conjunction endows the coordination polymer with diode-like photoelectronic behaviors, which hampers the inter- and intramol. photoinduced electron transfer from the triphenylamine-moiety to the Cu(II) site and permits reversed-directional ground-state electronic conductivity, rectifying the productive loop circuit for synergising photoredox and copper catalysis in pharmaceutically valuable decarboxylative C(sp3)-heteroatom couplings. The well-retained Cu(II) sites during photoirradiation exhibit unique inner-spheric modulation effects, which endow the couplings with adaptability to different types of nucleophiles and radical precursors under concise reaction conditions, and distinguish the multi-olefinic moieties of biointeresting steride derivatives in their late-stage trifluoromethylation-chloration difunctionalisation. The experimental process involved the reaction of Tris(4-bromophenyl)amine(cas: 4316-58-9Formula: C18H12Br3N)

In other references, Tris(4-bromophenyl)amine(cas: 4316-58-9) is often used in the synthesis of porous luminescent covalent–organic polymers (COPs)Formula: C18H12Br3N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Optimization of the benzamide fragment targeting the S2′ site leads to potent dipeptidyl peptidase-IV inhibitors》 was published in Bioorganic Chemistry in 2020. These research results belong to Deng, Xiaoyan; Wang, Na; Meng, Liuwei; Zhou, Siru; Huang, Junli; Xing, Junhao; He, Linhong; Jiang, Weizhe; Li, Qing. SDS of cas: 1129-28-8 The article mentions the following:

Our recently successful identification of benzoic acid-based DPP-4 inhibitors spurs the further quest for in-depth structure-activity relationships (SAR) study in S2′ site DPP-4. Thus novel benzamide fragments were designed to target the S2′ site to compromise lipophilicity and improve oral activity. Exploring SAR by introduction of a variety of amide and halogen on benzene ring led to identification of several compounds, exerting moderated to excellent DPP-4 activities, in which 4′-chlorine substituted Me amide, (R)-3-((4-(3-aminopiperidin-1-yl)-3-(but-2-yn-1-yl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl)-4-chloro-N-methylbenzamide hydro chloride (17g), [2380226-71-9], showed most potent DPP-4 activity with the IC50 value of 1.6 nM. Its activity was superior to reference alogliptin. Docking study ideally verified and interpreted the obtained SAR of designed compounds As a continuation, DPP-8/9 assays revealed the designed compounds exhibited good selectivity over DPP-8 and DPP-9. Subsequent cell-based test indicated (17g) displayed low toxicity toward the LO2 cell line up to 100μM. In vivo evaluation showed (17g) robustly improved the glucose tolerance in normal mice. Importantly, (17g) exhibited reasonable pharmacokinetic (PK) profiles for oral delivery. Overall, (17g) has the potential to a safe and efficacious DPP-4 inhibitor for T2DM treatment. In the experimental materials used by the author, we found Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8SDS of cas: 1129-28-8)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides. SDS of cas: 1129-28-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《A Widely Applicable Dual Catalytic System for Cross-Electrophile Coupling Enabled by Mechanistic Studies》 was published in ACS Catalysis in 2020. These research results belong to Charboneau, David J.; Barth, Emily L.; Hazari, Nilay; Uehling, Mycah R.; Zultanski, Susan L.. COA of Formula: C6H11BrO2 The article mentions the following:

A dual catalytic system for cross-electrophile coupling reactions between aryl halides and alkyl halides that features a Ni catalyst, a Co cocatalyst, and a mild homogeneous reductant is described. Mechanistic studies indicate that the Ni catalyst activates the aryl halide, while the Co cocatalyst activates the alkyl halide. This allows the system to be rationally optimized for a variety of substrate classes by simply modifying the loadings of the Ni and Co catalysts based on the reaction product profile. For example, the coupling of aryl bromides and aryl iodides with alkyl bromides, alkyl iodides, and benzyl chlorides is demonstrated using the same Ni and Co catalysts under similar reaction conditions but with different optimal catalyst loadings in each case. Our system is tolerant of numerous functional groups and is capable of coupling heteroaryl halides, di-ortho-substituted aryl halides, pharmaceutically relevant druglike aryl halides, and a diverse range of alkyl halides. Addnl., the dual catalytic platform facilitates a series of selective one-pot three-component cross-electrophile coupling reactions of bromo(iodo)arenes with two distinct alkyl halides. This demonstrates the unique level of control that the platform provides and enables the rapid generation of mol. complexity. The system can be readily utilized for a wide range of applications as all reaction components are com. available, the reaction is scalable, and toxic amide-based solvents are not required. It is anticipated that this strategy, as well as the underlying mechanistic framework, will be generalizable to other cross-electrophile coupling reactions. In the experiment, the researchers used Ethyl 4-bromobutyrate(cas: 2969-81-5COA of Formula: C6H11BrO2)

Ethyl 4-bromobutyrate(cas: 2969-81-5) belongs to bromides. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact.COA of Formula: C6H11BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Functional Janus dendrimers containing carbazole with liquid crystalline, optical and electrochemical properties》 was written by Iguarbe, Veronica; Barbera, Joaquin; Serrano, Jose Luis. Computed Properties of C7H13BrO2 And the article was included in Liquid Crystals in 2020. The article conveys some information:

Novel liquid crystalline Janus dendrimers that combine a mesogenic block and an electroactive block have been synthesized. The mesogenic block is based on two third-generation Percec-type dendrons bearing six or eight terminal dodecyloxy alkyl chains, whereas the electroactive blocks are formed by one or two carbazole units. The liquid crystal behavior was investigated by polarized-light optical microscopy, differential scanning microscopy and X-ray diffraction. The Janus dendrimers with one electroactive unit exhibited cubic or columnar liquid crystal phases, whereas the Janus dendrimers with two electroactive units did not show liquid crystalline behavior. The UV-vis absorption and emission properties of the Janus dendrimers were investigated. The spectra suggested the existence of π-π stacking and the formation of aggregates in the solid state. Electrodeposition of the carbazole-containing dendrimers afforded semi-globular particles in which the number of electropolymerizable units and the flexible or rigid character of the linker have a decisive influence in the particle size. In the experiment, the researchers used many compounds, for example, Ethyl 5-bromovalerate(cas: 14660-52-7Computed Properties of C7H13BrO2)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact.Computed Properties of C7H13BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Liquid crystal dimers containing Cholesteryl and Triazole-containing mesogenic units》 was written by Al-shargabi, Arwa; Yeap, Guan-Yeow; Mahmood, Wan Ahmad Kamil; Han, Chun-Chieh; Lin, Hong-Cheu; Ito, Masato M.. Safety of 8-Bromooctanoic acid And the article was included in Liquid Crystals in 2020. The article conveys some information:

New liquid crystals categorized as cholesteryl dimers have been successfully synthesized through the reaction between cholesteryl 4-(prop-2-ynyloxy)benzoate moieties with n-azido(cholesteryloxy-carbonyl)alkane. All the dimers display enantiotropic mesophases. While the odd-numbered dimers exhibit chiral nematic (N*), twisted grain boundary (TGB) and chiral smectic C (SmC*) phases, the even-numbered members from the same series show chiral smectic A and C. A detailed inspection on mesophase reveals that the chiral centers and the bent conformation of the odd-numbered members are essential for the induction of TGB phase. However, upon decreasing the temperature, the ratio of the transition temperatures (TSmC*-SmA*/TSmA*-I) is found to be 0.95, which indicate the second order transition according to the McMillan’s mol. theory. In addition, the X-ray diffraction study supports the presence of the smectic A phase on the even members rather than the N* by the appearance of the Bragg diffraction peaks at 190°. A comparison study with the other analogs in which the cholesterol entity is substituted by azobenzene or bipheny tails has been carried out to assess the relationship between the mol. structure and mesomorphic behavior.8-Bromooctanoic acid(cas: 17696-11-6Safety of 8-Bromooctanoic acid) was used in this study.

8-Bromooctanoic acid(cas: 17696-11-6) acid is used in the synthesis of 8-(N-Methyl-4,4′-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid. And 8-Bromooctanoic Acid is a useful compound for sonodynamic therapy.Safety of 8-Bromooctanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Nickel-catalyzed reductive coupling of homoenolates and their higher homologues with unactivated alkyl bromides》 was written by Lin, Tingzhi; Gu, Yuanyun; Qian, Pengcheng; Guan, Haixing; Walsh, Patrick J.; Mao, Jianyou. HPLC of Formula: 7051-34-5 And the article was included in Nature Communications in 2020. The article conveys some information:

A nickel-catalyzed generation of homoenolates, and their higher homologues, via decarbonylation of readily available cyclic anhydrides was developed. The utility of nickel-bound homoenolates and their higher homologues was demonstrated by cross-coupling with unactivated alkyl bromides, generated a diverse array of aliphatic acids. A broad range of functional groups was tolerated. Preliminary mechanistic studies demonstrated that the oxidative addition of anhydrides by the catalyst was faster than oxidative addition of alkyl bromides. The nickel bound metallocycles were involved in this transformation. The catalyst undergoes a single electron transfer (SET) process with the alkyl bromide. In the experiment, the researchers used (Bromomethyl)cyclopropane(cas: 7051-34-5HPLC of Formula: 7051-34-5)

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.HPLC of Formula: 7051-34-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Palladium-catalyzed C(sp3)-P(III) bond formation reaction with acylphosphines as phosphorus source》 was written by Zhang, Mengyue; Ma, Zhichao; Du, Hongguang; Wang, Zhiqian. Computed Properties of C4H7Br And the article was included in Tetrahedron Letters in 2020. The article conveys some information:

Pd-catalyzed C(sp3)-P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of Pd catalysis in C(sp3)-P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent. In the experiment, the researchers used (Bromomethyl)cyclopropane(cas: 7051-34-5Computed Properties of C4H7Br)

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.Computed Properties of C4H7Br

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides》 was written by Wang, Jiawen; He, Faqian; Yang, Xiaoyu. Application of 1530-32-1 And the article was included in Nature Communications in 2021. The article conveys some information:

Acyclic quaternary stereocenters are widely present in a series of biol. active natural products and pharmaceuticals. However, development of highly efficient asym. catalytic methods for the construction of these privileged motifs represents a longstanding challenge in organic synthesis. Herein, an efficient chiral phosphoric acid catalyzed direct asym. addition of α-alkynyl acyclic ketones with allenamides has been developed, furnishing the acyclic all-carbon quaternary stereocenters with excellent regioselectivities and high enantioselectivities. Extensive and detailed exptl. mechanistic studies were performed to investigate the mechanism of this reaction. Despite a novel covalent allyl phosphate intermediate was found in these reactions, further studies indicated that a SN2-type mechanism with the ketone nucleophiles is not very possible. Instead, a more plausible mechanisml involving the elimination of the allyl phosphate to give the α,β-unsaturated iminium intermediate, which underwent the asym. conjugate addition with the enol form of ketone nucleophiles under chiral anion catalysis, was proposed. In virtue of the fruitful functional groups bearing in the chiral products, the diverse derivatizations of the chiral products provided access to a wide array of chiral scaffolds with quaternary stereocenters. In addition to this study using Ethyltriphenylphosphonium bromide, there are many other studies that have used Ethyltriphenylphosphonium bromide(cas: 1530-32-1Application of 1530-32-1) was used in this study.

Ethyltriphenylphosphonium bromide(cas: 1530-32-1) is a phase transfer catalyst, used to accelerate the cure of phenolic-based epoxy resins, certain fluoroelastomer resins and thermosetting powder coatings. It is also used as catalysts in the synthesis of certain organic compounds and as a pharmaceutical intermediate.Application of 1530-32-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Furniel, Lucas G.; Echemendia, Radell; Burtoloso, Antonio C. B. published their research in Chemical Science in 2021. The article was titled 《Cooperative copper-squaramide catalysis for the enantioselective N-H insertion reaction with sulfoxonium ylides》.COA of Formula: C7H5BrO2 The article contains the following contents:

The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from a sulfur ylide, were described. By way of a catalytic asym. insertion reaction into N-H bonds from carbonyl sulfoxonium ylides and anilines, using a copper-bifunctional squaramide cooperative catalysis approach, thirty-seven α-arylglycine esters were synthesized in enantiomeric ratios up to 92:8 (99:1 after a single recrystallization) and reaction yields ranging between 49-96%. Furthermore, the protocol benefited from quick reaction times and was conducted in a straightforward manner. The experimental process involved the reaction of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4COA of Formula: C7H5BrO2)

Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.COA of Formula: C7H5BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary