Category: 39856-58-1

Pires, Marina J. D. published the artcileSynthesis of Substituted 4-, 5-, 6-, and 7-Azaindoles from Aminopyridines via a Cascade C-N Cross-Coupling/Heck Reaction, Name: 2-Bromopyridin-3-amine, the publication is Organic Letters (2016), 18(13), 3250-3253, database is CAplus and MEDLINE.

A practical palladium-catalyzed cascade C-N cross-coupling/Heck reaction of alkenyl bromides with amino-o-bromopyridines is described for a straightforward synthesis of substituted 4-, 5-, 6-, and 7-azaindoles using a Pd₂(dba)₃/XPhos/t-BuONa system. This procedure consists of the first cascade C-N cross-coupling/Heck approach toward all four azaindole isomers from available aminopyridines. The scope of the reaction was investigated and several alkenyl bromides were used, allowing access to different substituted azaindoles. This protocol was further explored for N-substituted amino-o-bromopyridines.

Organic Letters published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Name: 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Azizollahi, Hamid published the artcileSynthesis of [3.4]-Spirooxindoles through Cascade Carbopalladation of Skipped Dienes, Recommanded Product: 2-Bromopyridin-3-amine, the publication is Advanced Synthesis & Catalysis (2020), 362(9), 1899-1904, database is CAplus.

A synthetic route to [3.4]-spirooxindoles based on cascade carbopalladation reactions of 1,4-dienes was described. While carbopalladation of alkenes have been used to access mainly [4.4]- or [4.5]-spirocycles, 4-exo-trig carbopalladation was not been yet applied to the synthesis of relevant [3.4]-spirooxindole scaffolds bearing a cyclobutyl ring. In addition, the cascade reaction generates an exocyclic double bond that can serve as a platform to further diversify the substitution pattern of the spirooxindole nuclei.

Advanced Synthesis & Catalysis published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Recommanded Product: 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Berger, Olivier published the artcilePhosphorus-Carbon Bond Formation: Palladium-Catalyzed Cross-Coupling of H-Phosphinates and Other P(O)H-Containing Compounds, Computed Properties of 39856-58-1, the publication is Advanced Synthesis & Catalysis (2013), 355(7), 1361-1373, database is CAplus.

Two generally applicable systems were developed for the cross-coupling of P(O)H compounds with C_sp2-X and related partners. Pd catalysis using a ligand/additive combination, typically either xantphos/ethylene glycol or 1,1′-bis(diphenylphosphino)ferrocene/1,2-dimethoxyethane, with diisopropylethylamine as the base, proved to be generally useful for the synthesis of numerous P-C containing compounds E.g., reaction of RP(O)(OEt)H (R = octyl) with 2-bromopyridine in the presence of 2 mol% Pd(OAc)₂/xantphos, toluene and ethylene glycol and (ⁱPr)₂NEt at 115° to give 93% yield of (Oct)P(O)(OEt)(2-pyridyl). Routinely, 2 mol% of catalyst are employed (less than half the amount typically employed in most other literature reports). In most cases, excellent results were obtained with a variety of electrophiles (RX, where R = alkenyl, allyl, alkynyl, etc.). The full account of the studies is disclosed, including tandem hydrophosphinylation/coupling and coupling/coupling for doubly catalytic P-C bond formation. The methodol. compares favorably with any existing literature report. The use of an additive appears to be a generally useful strategy to control the reactivity of phosphinylidene compounds

Advanced Synthesis & Catalysis published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Computed Properties of 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Purificacao, Sara I. published the artcileOne-Pot Synthesis of 1,2-Disubstituted 4-, 5-, 6-, and 7-Azaindoles from Amino-o-halopyridines via N-Arylation/Sonogashira/Cyclization Reaction, SDS of cas: 39856-58-1, the publication is Organic Letters (2017), 19(19), 5118-5121, database is CAplus and MEDLINE.

A direct synthesis of several 1,2-disubstituted 4-, 5-, 6-, and 7-azaindoles from available amino-o-halopyridines is described. This procedure involves a palladium-catalyzed N-arylation followed by a Sonogashira reaction and subsequent cyclization in a one-pot manner, exhibiting a wide scope and compatibility with electron-withdrawing and electron-donating groups. The strategy represents an advancement in azaindole chem. with a straightforward approach toward 1,2-disubstituted azaindoles, while avoiding complex N-arylations of hindered 2-substituted azaindoles and difficult purification steps of intermediates.

Organic Letters published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, SDS of cas: 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Nguyen, Phuhai published the artcileEvaluation of the antiprion activity of 6-aminophenanthridines and related heterocycles, COA of Formula: C5H5BrN2, the publication is European Journal of Medicinal Chemistry (2014), 363-371, database is CAplus and MEDLINE.

Several 6-(amino)phenanthridine derivatives and related heterocyclic compounds such as benzonaphtyridine derivatives were prepared A reduction of one of the three aromatic rings was also performed. The compounds were first tested for their antiprion activity in a previously described yeast-based colorimetric prion assay. The most potent derivatives were then assayed ex-vivo against the mammalian prion PrP^Sc in a cell-based assay. Several of the new compounds were found more potent than the parent lead 6-aminophenanthridine. The most promising compounds against yeast and mammalian prions were 8-azido-6-aminophenanthridine and 7,10-dihydrophenanthridin-6-amine. In the mammalian cell-based assay, the IC₅₀ of these two compounds were around 5 μM and 1.8 μM, resp. The synthesis of the target compounds was achieved by a coupling reaction of boronic acid esters, such as 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile with suitable aryl bromides or aryl chlorides. The tilte compounds thus formed included 6-phenanthridinamine derivatives and analogs, such as benzo[c][2,6]naphthyridin-5-amine, benzo[h][1,6]naphthyridin-5-amine, benzo[c][1,8]naphthyridin-6-amine, benzo[c][1,6]naphthyridine, benzo[c]-1,5-naphthyridine.

European Journal of Medicinal Chemistry published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, COA of Formula: C5H5BrN2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yang, Lei published the artcileChiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C-H Arylation, Product Details of C5H5BrN2, the publication is Angewandte Chemie, International Edition (2018), 57(5), 1394-1398, database is CAplus and MEDLINE.

Previous enantioselective Pd⁰-catalyzed C-H activation reactions proceeding via the concerted metalation-deprotonation mechanism employed either a chiral ancillary ligand, a chiral base, or a bimol. mixture thereof. This study describes the development of new chiral bifunctional ligands based on a binaphthyl scaffold which incorporates both a phosphine and a carboxylic acid moiety. The optimal ligand provided high yields and enantioselectivities for a desymmetrizing C(sp²)-H arylation leading to 5,6-dihydrophenanthridines, whereas the corresponding monofunctional ligands showed low enantioselectivities. The bifunctional system proved applicable to a range of substituted dihydrophenanthridines, and allowed the parallel kinetic resolution of racemic substrates.

Angewandte Chemie, International Edition published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C14H10O4S2, Product Details of C5H5BrN2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Larionov, Evgeny published the artcileScope and mechanism of asymmetric C(sp³)-H/C(Ar)-X coupling reactions: computational and experimental study, Recommanded Product: 2-Bromopyridin-3-amine, the publication is Chemical Science (2013), 4(5), 1995-2005, database is CAplus.

Advances in the efficient palladium-NHC catalyzed synthesis of highly enantioenriched 2,3-trans-fused and 2-alkyl indolines by an asym. C(sp³)-H activation of an unactivated methylene/methyl group are reported. Very high asym. inductions (up to 99% ee) were achieved at reaction temperatures ranging from 120-160°. Factors influencing the efficiency of the reaction (halide, pseudohalide, N-protecting group) were investigated. The reaction pathway and enantioselection were probed by detailed d. functional theory (DFT) calculations (M06-L functional). The combined theor. and exptl. study shows that the Pd-NHC catalyzed C(sp³)-H arylation proceeds via a concerted metalation-deprotonation (CMD) mechanism. The CMD step is shown by DFT calculations and kinetic isotope effect measurements to be selectivity-determining A good agreement between exptl. enantioselectivities and calculated differences amongst diastereomeric activation barriers is observed

Chemical Science published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Recommanded Product: 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Venkateshwarlu, Rapolu published the artcileUltrasound assisted one-pot synthesis of 1,2-diaryl azaindoles via Pd/C-Cu catalysis: Identification of potential cytotoxic agents, Application of 2-Bromopyridin-3-amine, the publication is Tetrahedron Letters (2019), 60(52), 151326, database is CAplus.

Ultrasound assisted one-pot and direct access to 1,2-diaryl substituted azaindole derivatives I [W = CH, N; X = CH, N; Y = CH, N; Z = CH, N; Ar¹ = Ph, 4-ClC₆H₄, 4-MeC₆H₄; Ar² = 4-CNC₆H₄, 4-MeOC₆H₄, 4-Me(SO₂)C₆H₄, etc.] was achieved via the sequential N-arylation followed by coupling-cyclization under Pd/C-Cu catalysis. The methodol. involved initial C-N bond forming reaction (step 1) between an appropriate o-bromo substituted amino pyridine and iodoarene followed by C-C and C-N bond formation (step 2) between the resulting N-aryl substituted intermediate and a terminal alkyne in the same pot. A variety of azaindoles were prepared by using this method. These compounds were assessed for their cytotoxic properties against two different metastatic breast cancer cell lines e.g. MDA-MB-231 and MCF-7. Compounds I [W = Y = Z = CH, X = N, Ar¹ = 4-MeC₆H₄, Ar² = 4-MeOC₆H₄], I [W = Y = Z = CH, X = N, Ar¹ = Ph, Ar² = 4-MeOC₆H₄] and I [W = Y = Z = CH, X = N, Ar¹ = 4-ClC₆H₄, Ar² = 3,5-di-MeOC₆H₃] showed promising growth inhibition of these cell lines and SIRT1 inhibition in vitro.

Tetrahedron Letters published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C15H24O2, Application of 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Tolmachova, Kateryna A. published the artcile(Chlorosulfonyl)benzenesulfonyl Fluorides-Versatile Building Blocks for Combinatorial Chemistry: Design, Synthesis and Evaluation of a Covalent Inhibitor Library, Recommanded Product: 2-Bromopyridin-3-amine, the publication is ACS Combinatorial Science (2018), 20(11), 672-680, database is CAplus and MEDLINE.

Multigram synthesis of (chlorosulfonyl)benzenesulfonyl fluorides is described. Selective modification of these building blocks at the sulfonyl chloride function under parallel synthesis conditions is achieved. It is shown that the reaction scope includes the use of (hetero)aromatic and electron-poor aliphatic amines (e.g., amino nitriles). Utility of the method is demonstrated by preparation of the sulfonyl fluoride library for potential use as covalent fragments, which is demonstrated by a combination of in silico and in vitro screening against trypsin as a model enzyme. As a result, several inhibitors were identified with activity on par with that of the known inhibitor.

ACS Combinatorial Science published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C19H14N2, Recommanded Product: 2-Bromopyridin-3-amine.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Lessing, Timo published the artcileActivation-free one-pot alkynylation-cyclization synthesis of 2-substituted 4-azaindoles and indoles, Application In Synthesis of 39856-58-1, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2018), 54(3), 334-338, database is CAplus.

2-Substituted 4-azaindoles and indoles were rapidly and efficiently prepared in an activation-free Pd-catalyzed alkynylation-cyclization sequence starting from 3-amino-2-bromopyridine or o-bromoaniline and terminal alkynes in a one-pot fashion.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Application In Synthesis of 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem