Tag: M.W=200-250

Handa, Sachin published the artcileSustainable Fe-ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water, Application In Synthesis of 844501-00-4, the publication is Science (Washington, DC, United States) (2015), 349(6252), 1087-1091, database is CAplus and MEDLINE.

Iron nanoparticles containing ppm quantities of palladium were effective for Suzuki-Miyaura coupling reactions of boronic acids, trifluoroborates, and N-methyliminodiacetic acid boronates with aryl and heteroaryl bromides and iodides in aqueous solutions containing the com. available surfactant TPGS-750-M. Treatment of FeCl₃ (naturally containing 320 ppm Pd) with a phosphine ligand, particularly SPhos {dicyclohexyl(2′,6′-dimethoxy[1,1′-biphenyl]-2-yl)phosphine} or XPhos, in THF with a Grignard reagent in THF yielded Fe nanoparticles which were used as Suzuki-Miyaura coupling reaction catalysts with K₃PO₄ as base. The activity of the nanoparticles depended strongly on the iron source and the ligand used. The nanoparticles were recycled after extraction of product; for every two cycles, roughly 160 ppm Pd(OAc)₂ was added to replace leached palladium.

Science (Washington, DC, United States) published new progress about 844501-00-4. 844501-00-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Amide,Boronic Acids,Boronic acid and ester, name is (1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid, and the molecular formula is C10H18BNO4, Application In Synthesis of 844501-00-4.

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

Rej, Rohan Kalyan published the artcileEEDi-5285: An Exceptionally Potent, Efficacious, and Orally Active Small-Molecule Inhibitor of Embryonic Ectoderm Development, Name: (1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid, the publication is Journal of Medicinal Chemistry (2020), 63(13), 7252-7267, database is CAplus and MEDLINE.

Inhibition of embryonic ectoderm development (EED) is a new cancer therapeutic strategy. Herein, we report our discovery of EEDi-5285 as an exceptionally potent, efficacious, and orally active EED inhibitor. EEDi-5285 binds to the EED protein with an IC₅₀ value of 0.2 nM and inhibits cell growth with IC₅₀ values of 20 pM and 0.5 nM in the Pfeiffer and KARPAS422 lymphoma cell lines, resp., carrying an EZH2 mutation. EEDi-5285 is approx. 100 times more potent than EED226 in binding to EED and >300 times more potent than EED226 in inhibition of cell growth in the KARPAS422 cell line. EEDi-5285 has excellent pharmacokinetics and achieves complete and durable tumor regression in the KARPAS422 xenograft model in mice with oral administration. The cocrystal structure of EEDi-5285 in a complex with EED defines the precise structural basis for their high binding affinity. EEDi-5285 is the most potent and efficacious EED inhibitor reported to date.

Journal of Medicinal Chemistry published new progress about 844501-00-4. 844501-00-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Amide,Boronic Acids,Boronic acid and ester, name is (1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid, and the molecular formula is C10H18BNO4, Name: (1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid.

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

Chen, Changpeng published the artcilePalladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines, HPLC of Formula: 107263-95-6, the publication is Journal of Organic Chemistry (2015), 80(2), 942-949, database is CAplus and MEDLINE.

A novel and efficient synthetic method for o-fluorobenzylamines via palladium catalyst using an easily accessible oxalyl amide as directing group has been developed. The cheap N-fluorobenzenesulfonimide could be used as an effective [F⁺] source and t-amyl-OH as the solvent with Pd(OAc)₂ as catalyst. Selective mono- or difluorination of oxalyl amide-protected benzylamine derivatives were achieved by modifying the reaction conditions, which presented an efficient method for the preparation of ortho-fluorinated benzylamines.

Journal of Organic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, HPLC of Formula: 107263-95-6.

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

Umemoto, Teruo published the artcileHighly Selective Fluorinating Agents: a Counteranion-Bound N-Fluoropyridinium Salt System, COA of Formula: C6H5F4NO3S, the publication is Journal of Organic Chemistry (1995), 60(20), 6563-70, database is CAplus.

A series of alkyl- or (trifluoromethyl)-substituted N-fluoropyridinium 2-sulfonates 2a-h, differing in fluorinating power, were synthesized, and assessment was made of the effectiveness of each selective fluorinating agent. N-Fluoropyridinium 3- and 4-sulfonates were also synthesized. Power-variables 2a-h were found to be highly selective fluorinating agents for a wide range of nucleophilic substrates such as activated aromatics, enol trialkylsilyl and alkyl ethers, active methylene compounds, activated olefins, and sulfides. This regioselectivity increased with the bulkiness of the silyl part, and with the most bulky triisopropylsilyl group exclusive 6-fluorination was achieved. Preferential β-stereoselective fluorination at the 6-position was observed N-Fluoropyridinium 2-sulfonates were activated with an acid. This acid-catalyzed fluorination led to the preferential p-fluorination of anisole. The present results can be explained based on the capacity of the 2-sulfonate anion to interact with the hydroxy group of phenol or naphthol, NH group of phenylurethane, silicon atoms of silyl ethers, or protons of acids.

Journal of Organic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C12H9NO, COA of Formula: C6H5F4NO3S.

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

Umemoto, Teruo published the artcilePreparation of 2-fluoropyridines via base-induced decomposition of N-fluoropyridinium salts, Safety of 1-Fluoropyridiniumtriflate, the publication is Journal of Organic Chemistry (1989), 54(7), 1726-31, database is CAplus.

N-Fluoropyridinium salts with either BF₄^–, SbF₆^–, or PF₆^– as the counterion were treated with excess base, such as Et₃N, at room temperature to give 2-fluoropyridines in good yield. This method was successfully applied to the preparation of 2-fluoropyridine derivatives possessing electron-donating or withdrawing substituents from the substituted N-fluoropyridinium tetrafluoroborates. Pyridine-F₂ compounds produced through reactions of pyridines with mol. F (caution, toxic) were also treated with a base to give 2-fluoropyridines but in low yields. These reactions are considered to occur through a carbene mechanism as follows: a novel N-F-containing cyclic carbene generated from the N-fluoropyridinium salts by 2-proton abstraction, reacts with F atoms from the counterions, followed by elimination of F^– from the N-F moiety to yield 2-fluoropyridines. Previously reported findings in reactions of pyridines with mol. F are explained on the basis of this mechanism.

Journal of Organic Chemistry published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C27H39ClN2, Safety of 1-Fluoropyridiniumtriflate.

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

Umemoto, Teruo published the artcileBase-initiated reactions of N-fluoropyridinium salts; a novel cyclic carbene proposed as a reactive species, Name: 1-Fluoropyridiniumtriflate, the publication is Tetrahedron Letters (1987), 28(24), 2705-8, database is CAplus.

Deprotonation of 1-fluoropyridinium triflate with Et₃N gave cyclic carbene I, which reacted with the solvent (e.g. CH₂Cl₂, CH₂Br₂, MeCN, C₆H₆, Me₂CO) to give 5-62% electrophilic trapping products, e.g. II (R = Cl, Br, NHAc, Ph, OCFMe₂), 7-42% 2-pyridyl triflate (II, R = O₃SCF₃), and 4-15% 2-fluoropyridine (II, R = F).

Tetrahedron Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C10H11NO4, Name: 1-Fluoropyridiniumtriflate.

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

Nishiwaki, Nagatoshi published the artcileThree components ring transformation affording substituted 5-nitropyridines and 4-nitroanilines, Recommanded Product: 5-Nitro-2-phenylpyridine, the publication is Letters in Organic Chemistry (2006), 3(8), 629-633, database is CAplus.

The ring transformation of 1-methyl-3,5-dinitro-2-pyridone afforded 2-aryl-5-nitropyridines upon treatment with aromatic ketones in the presence of ammonium acetate. In reactions with aliphatic ketones, 2,6-disubstituted 4-nitroanilines could be prepared in addition to 2,3-disubstituted 5-nitropyridines. In these reactions, dinitropyridone behaved as the synthetic equivalent of unstable nitromalonaldehyde.

Letters in Organic Chemistry published new progress about 89076-64-2. 89076-64-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitro Compound,Benzene, name is 5-Nitro-2-phenylpyridine, and the molecular formula is C11H8N2O2, Recommanded Product: 5-Nitro-2-phenylpyridine.

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

Lohse, Olivier published the artcileThe palladium-catalyzed Suzuki coupling of 2- and 4-chloropyridines, Name: 5-Nitro-2-phenylpyridine, the publication is Synlett (1999), 45-48, database is CAplus.

The Suzuki coupling of 2- and 4-chloropyridines with arylboronates is successfully performed under Pd(PPh₃)₄ catalysis. Moderate to good yields are obtained with 4-chloropyridines, while 2-chloropyridines give excellent yields. The corresponding pyridine N-oxides react in the same manner. An easy and cheap access to arylpyridines, is thus achieved.

Synlett published new progress about 89076-64-2. 89076-64-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitro Compound,Benzene, name is 5-Nitro-2-phenylpyridine, and the molecular formula is C11H8N2O2, Name: 5-Nitro-2-phenylpyridine.

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

Ueno, Tetsuya published the artcileSynthesis and properties of fluoroazulenes. II. Electrophilic fluorination of azulenes with N-fluoro reagents, Name: 1-Fluoropyridiniumtriflate, the publication is Bulletin of the Chemical Society of Japan (1996), 69(6), 1645-1656, database is CAplus.

1-Fluoro- and 1,3-difluoroazulenes were synthesized for the first time by the electrophilic fluorination of azulenes with N-fluoro reagents. Selective preparation of 1-fluoroazulenes were performed by the fluorination of Me azulene-1-carboxylates, followed by demethoxycarbonylation in 100% H₃PO₄. 2-Substituted azulenes were fluorinated in higher yields. In the ¹H NMR of 1-fluoroazulene, long-range J_FH values were not observed at H-2 and H-8, in contrast to those for 1-fluoronaphthalene. The 1-fluorine atom causes significant bathochromic shifts in the visible absorption of azulene, due to the so-called +Iπ effect.

Bulletin of the Chemical Society of Japan published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C13H14N2O, Name: 1-Fluoropyridiniumtriflate.

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

Ueno, Tetsuya published the artcilesynthesis of 1-fluoro- and 1,3-difluoroazulenes, Recommanded Product: 1-Fluoropyridiniumtriflate, the publication is Chemistry Letters (1995), 169-70, database is CAplus.

Title compounds were synthesized by the reaction of azulene with N-fluoropyridinium salts in MeCN. Me azulene-1-carboxylates were also fluorinated to give the corresponding 3-fluoro derivatives On the basis of the UV-visible absorption spectra, the fluorine atom acts as an electron-donating group to the azulene π-system due to the +Iπ effect. A solution of azulene and N-fluoro-2,4,6-trimethylpyridinium triflate in MeCN were refluxed to give 1-fluoroazulene and 1,3-difluoroazulene. The yields of these 2 compounds decreased with more powerful fluorinating agents.

Chemistry Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C19H17N2NaO4S, Recommanded Product: 1-Fluoropyridiniumtriflate.

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