Category: 89694-44-0

Cardenas, Mariel M. published the artcileEnantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution, Related Products of bromides-buliding-blocks, the publication is Organic Letters (2018), 20(7), 2037-2041, database is CAplus and MEDLINE.

The catalytic enantioselective synthesis of 3-aryl-substituted pyrrolopyrimidines (PPYs), a common motif in drug discovery, is achieved through a kinetic resolution via quaternary ammonium salt-catalyzed nucleophilic aromatic substitution (S_NAr). Both enantioenriched products and starting materials can be functionalized with no observed racemization to give enantiodivergent access to diverse chiral analogs of an important class of kinase inhibitor. One of the compounds was found to be a potent and selective inhibitor of breast tumor kinase.

Organic Letters published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Akitake, Masahiro published the artcileAccess to γ-Carbolines: Synthesis of Isocryptolepine, Quality Control of 89694-44-0, the publication is Journal of Organic Chemistry (2021), 86(24), 17727-17737, database is CAplus and MEDLINE.

A new method to synthesize γ-carboline derivatives has been developed starting from 3,5-dibromo-4-pyridinamine by monoarylation using the Suzuki-Miyaura cross-coupling reaction followed by the base-mediated ring closure to pyrrole formation. Synthesis of a series of γ-carboline derivations from the 4-brominated γ-carboline 4a has been achieved by employing various coupling reactions and N-alkylations. This method has been applied for the synthesis of the antimalarial and anticancer natural product isocryptolepine. The photophys. properties of novel γ-carboline derivations are also reported.

Journal of Organic Chemistry published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Quality Control of 89694-44-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Tsukamoto, Hirokazu published the artcileScalable Total Syntheses and Structure-Activity Relationships of Haouamines A, B, and Their Derivatives as Stable Formate Salts, Formula: C7H8BBrO3, the publication is Chemistry – A European Journal (2020), 26(55), 12528-12532, database is CAplus and MEDLINE.

Haouamines A, B, and their derivatives were synthesized via Suzuki-Miyaura coupling and three key cyclization reactions as follows: the newly developed palladium(0)-catalyzed arylative cyclization of phenylalanine-derived alkyne-aldehydes with 2-bromoarylboronic acid (an “anti-Wacker”-type cyclization); BF₃·OEt₂-promoted Friedel-Crafts-type cyclization of sym. electron-rich aromatic rings adjacent to a tertiary allylic alc. leading to the indeno-tetrahydropyridine skeleton; and (cyanomethyl)trimethylphosphonium iodide-mediated macrocyclization of amino alcs. to afford aza-paracyclophane precursors. The palladium-catalyzed reduction of mono- and di-triflate intermediates in the later stages enabled the alteration of both the position and number of hydroxyl groups on the C-ring. The instability of haouamine B was dramatically improved by salt formation with formic acid. An unambiguous evaluation of the cytotoxicity of the prepared haouamine derivative formates with and without hydroxyl groups at different positions on the C-ring indicated that the catechol structure in haouamine B produced weak cytotoxicity.

Chemistry – A European Journal published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C9H8O4, Formula: C7H8BBrO3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Maddox, Sean M. published the artcileA Practical Lewis Base Catalyzed Electrophilic Chlorination of Arenes and Heterocycles, Computed Properties of 89694-44-0, the publication is Organic Letters (2015), 17(4), 1042-1045, database is CAplus and MEDLINE.

A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodol. is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chem. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.

Organic Letters published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Computed Properties of 89694-44-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Harada, Yasuyuki published the artcileRh(I)-Catalyzed Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Leading to Indenones, Application of 2-Bromo-5-methoxybenzene boronic acid, the publication is Journal of the American Chemical Society (2007), 129(17), 5766-5771, database is CAplus and MEDLINE.

The Rh-catalyzed reaction of alkynes with 2-bromophenylboronic acids involves carbonylative cyclization to give indenones. The key steps in the reaction involve the addition of an arylrhodium(I) species to an alkyne and the oxidative addition of C-Br bonds on the adjacent Ph ring to give vinylrhodium(I) species II. The regioselectivity depends on both the electronic and the steric nature of the substituents on the alkynes. A bulky group and an electron-withdrawing group favor the α-position of indenones. In the case of silyl- or ester-substituted alkynes, the regioselectivity is extremely high. The selectivity increases in the order SiMe₃ > COOR ≫ aryl ≫ alkyl. The reaction of norbornene with 2-bromophenylboronic acids under 1 atm of CO gives the corresponding indanone derivative The reaction of alkynes with 2-bromophenylboronic acids under nitrogen gives naphthalene derivatives, in which two mols. of alkynes are incorporated. A vinylrhodium complex similar to II can also be generated by a different route by employing 2-bromophenyl(trimethylsilyl)acetylene and arylboronic acids in the presence of Rh(I) complex as the catalyst, resulting in the formation of indenones. The reaction of 1-(2-bromophenyl)-hept-2-yn-1-one with PhB(OH)₂ in the presence of Rh(I) complex also resulted in carbonylative cyclization to give an indan-1,3-dione derivative

Journal of the American Chemical Society published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Application of 2-Bromo-5-methoxybenzene boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Razuvaev, G. A. published the artcileReactions of triethylaluminum and triphenylaluminum with benzoyl peroxide in benzene solution, Related Products of bromides-buliding-blocks, the publication is Zhurnal Obshchei Khimii (1961), 2340-3, database is CAplus.

cf. Ziegler, Ger. (East) 13539 and Ger. (East) 24757. Reaction of Et₃Al with Bz₂O₂ in C₆H₆ was exothermic and required cooling; run at 25-35°, the reaction gave Et₂AlOBz and EtOBz; at higher temperature, the reaction was very complex and no definite products could be isolated. Approx. 3% Bz₂O₂ failed to react regardless of reagent proportions and the reaction, while very vigorous at first, slowed abruptly in further progress. Ph₃Al and Bz₂O₂ under similar conditions gave Ph₂AlOBz, m. 159-60°, some PhOBz, and C₆H₆.

Zhurnal Obshchei Khimii published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Smith, Davis E. published the artcileExploiting Atropisomerism to Increase the Target Selectivity of Kinase Inhibitors, Related Products of bromides-buliding-blocks, the publication is Angewandte Chemie, International Edition (2015), 54(40), 11754-11759, database is CAplus and MEDLINE.

Many biol. active mols. exist as rapidly interconverting atropisomeric mixtures Whereas one atropisomer inhibits the desired target, the other can lead to off-target effects. Herein, we study atropisomerism as a possibility to improve the selectivities of kinase inhibitors through the synthesis of conformationally stable pyrrolopyrimidines. Each atropisomer was isolated by HPLC on a chiral stationary phase and subjected to inhibitor profiling across a panel of 18 tyrosine kinases. Notably different selectivity patterns between atropisomers were observed, as well as improved selectivity compared to a rapidly interconverting parent mol. Computational docking studies then provided insights into the structure-based origins of these effects. This study is one of the first examples of the intentional preorganization of a promiscuous scaffold along an atropisomeric axis to increase target selectivity, and provides fundamental insights that may be applied to other atropisomeric target scaffolds.

Angewandte Chemie, International Edition published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C12H17NO2, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Nechaev, Anton A. published the artcileSynthesis of fused 1,2-naphthoquinones with cytotoxic activity using a one-pot three-step reaction, Computed Properties of 89694-44-0, the publication is Organic & Biomolecular Chemistry (2021), 19(15), 3434-3440, database is CAplus and MEDLINE.

A method for the synthesis of fused 1,2-naphthoquinones, as analogs of biol. active natural terpene quinones, was described. The intermediate polycyclic naphthalenes were prepared by a one-pot palladium-catalyzed process from simple alkynes, one of which was made from an optically pure biomass-derived levoglucosenone. The prepared methoxy-substituted naphthalenes were subsequently transformed in one step to 1,2-naphthoquinones by a trivalent-iodine-mediated oxidation The naphthoquinone products were found to have cytotoxic properties.

Organic & Biomolecular Chemistry published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Computed Properties of 89694-44-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Matsuzawa, Tsubasa published the artcileTransition-Metal-Free Synthesis of N-Arylphenothiazines through an N- and S-Arylation Sequence, Computed Properties of 89694-44-0, the publication is Organic Letters (2021), 23(6), 2347-2352, database is CAplus and MEDLINE.

An efficient synthetic method of N-arylphenothiazines, e.g., I, from o-sulfanylanilines under transition-metal-free conditions is disclosed. An N- and S-arylation sequence of o-sulfanylanilines enabled the authors to synthesize a wide variety of N-arylphenothiazines. In particular, one-pot synthesis of N-arylphenothiazines was accomplished from easily available modules through preparation of o-sulfanylanilines by thioamination of aryne intermediates and following N- and S-arylation sequence.

Organic Letters published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Computed Properties of 89694-44-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Sui, Jingzhi published the artcileSynthesis of Trans-4a,12b/3,4-Dihydrodibenzo[f,h]quinolin-2(1H)-Ones and Dibenzo[f,h]quinolin-2(1H)-Ones via Irradiation of 6-Biphenylpyridine-2(1H)-Ones, Product Details of C7H8BBrO3, the publication is Advanced Synthesis & Catalysis (2021), 363(14), 3554-3559, database is CAplus.

The synthesis of trans-4a,12b-dihydrodibenzo[f,h]quinolin-2(1H)-ones, dibenzo[f,h]quinolin-2(1H)-ones and 3,4-dihydrodibenzo[f,h]quinolin-2(1H)-ones via photo-induced annulation of 6-([1,1′-biphenyl]-2-yl)pyridine-2(1H)-ones under irradiation of a 313 nm UV light was described. Trans-4a,12b-dihydrodibenzo[f,h]quinolin-2(1H)-ones were obtained in 82-95% yields when the irradiation time was 3 h. Dibenzo[f,h]quinolin-2(1H)-ones were obtained by irradiating biphenylpyridinones for 12 h in the presence of iodine. Heating the solution of trans-4a,12b-dihydrodibenzo[f,h]quinolin-2(1H)-ones in DMF at 130°C for 24 h gave 3,4-dihydrodibenzo[f,h]quinolin-2(1H)-ones via a double 1,3-H shift. The demonstrated protocols showed the diversity of photo-induced cyclization of biphenylpyridinones.

Advanced Synthesis & Catalysis published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is CBF6K, Product Details of C7H8BBrO3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary