13737-05-8

Usage

Uses

Used in Pharmaceutical Industry:
TRIMETHYL(2-PYRIDYL)TIN is used as a synthetic intermediate for the preparation of L-mannonic acid derivatives, which are crucial in the development of HIV-1 protease inhibitors. These inhibitors play a vital role in the treatment of HIV/AIDS by blocking the activity of the HIV-1 protease enzyme, thereby preventing the formation of mature, infectious viral particles.
Used in Medicinal Chemistry:
TRIMETHYL(2-PYRIDYL)TIN is also utilized in the synthesis of aryl indole NK1 receptor antagonists. These antagonists are important in the development of drugs targeting the neurokinin 1 receptor, which is involved in various physiological processes and diseases, including pain, inflammation, and depression. By modulating the activity of the NK1 receptor, these antagonists can potentially provide therapeutic benefits in the treatment of these conditions.

Upstream product

• 109-04-6 2-bromo-pyridine 
• 1066-45-1 trimethyltin(IV)chloride 
• 7440-23-5 sodium 
• 33675-27-3 trimethylpyridin-2-ylammonium iodide 
• 34039-95-7 (2-pyridyl)diethylphosphate 
• 1256814-27-3 diethyl 5-chloropyridin-2-yl phosphate 
• 53682-85-2 diethyl 2-chloropyridin-3-yl phosphate 
• 1256814-29-5 2,3-bis[(diethoxyphosphoryl)oxy]pyridine 
• 661-69-8 hexamethyldistannane 
• 504-29-0 2-aminopyridine 
• 109-09-1 2-chloropyridine 
• 5029-67-4 2-iodopyridine 

Downstream Products

• 581-50-0 2,3'-bipyridine 
• 91-02-1 phenyl(pyridin-2-yl)methanone 
• 5691-08-7 2-(pyridin-2-yl)-indole-3-carbaldehyde 
• 1148-79-4 2,2':6,2''-terpyridine 
• 2524-52-9 ethyl-2-picolinate 
• 1122-62-9 2-acetylpyridine 
• 197177-71-2 2,2-dimethyl-N-{2-[3-fluoro-4-(2-pyridyl)-2-pyridyl]phenyl}propanamide 
• 203573-76-6 2,2'-dipyridyl-6-carboximidic acid methyl ester 
• 58792-53-3 2,2'-bipyridine-5-carboxylic acid methyl ester 
• 15009-91-3 2-nitropyridine 
• 15862-19-8 5-bromo-2,2'-bipyridyl 
• 10495-73-5 2-bromo-6-(pyridin-2-yl)pyridine 
• 512179-12-3 5'-O-(4,4'-dimethoxytrityl)-5-((2,2'-bipyridin-6-yl)ethynyl)-2'-deoxyuridine 
• 254974-21-5 5-[2-(5-chloro-2-methoxybenzamido)ethyl]-2-(2-pyridyl)benzenesulfonamide 

Relevant academic research and scientific papers

ZUR SYNTHESE EINIGER NEUER HETEROCYCLISCH SUBSTITUIERTER STANNANE

The in 2-position trimethylstannylated heterocycles are formed in good yields by reaction of the lithiated heterocycles benzothiazole, N-methylbenzimidazole, N-methylimidazole, N-methyltriazole, pyridine, chinoline and thiazole with trimethylchlorostannane.The thermolabile lithium compounds are synthesized by metallation or by metal-halogen exchange reactions according to known procedures.

Synthesis and molecular structures of 2-trimethylsilyl-, 2-trimethylgermyl-, and 2-trimethylstannyl-pyridines

5-Methyl-2-trimethylsilyl-pyridine (1) has recently been prepared via the "in situ" Grignard reaction of 1-bromo-5-methyl-pyridine with magnesium and trimethylchlorosilane in refluxing tetrahydrofuran (thf) and structurally characterized. 2-Trimethylgermyl-(2) and 2-trimethylstannyl-pyridine (3) were now obtained from 2-bromo-pyridine through metallation (with n-BuLi) and treatment of the intermediates with Me3GeBr and Me3SnC1, respectively, in diethylether/ thf at -70°C. The crystal and molecular structure of compound 2 has been determined by low temperature (in situ) single crystal X-ray diffraction methods. There is a significant bending of the Me3Ge substituent towards the nitrogen heteroatom [Ge-C-N = 114.7(2)°]. This phenomenon is known from previous studies of the silicon analogue 1 to be not due to intramolecular (peripheral) Si/Ge←N coordination, but to be rather an intrinsic property of the heteroarene skeleton, as also confirmed by quantum-chemical calculations. Furthermore, there is no evidence for intermolecular coordination in the crystals. Such interactions could also be ruled out for the solution state of 2 and 3 through variable temperature multinuclear NMR investigations.

ATF6 INHIBITORS AND USES THEREOF

Compounds as inhibitors of Activating Transcription Factor 6 (ATF6) are provided. The compounds may find use as therapeutic agents for the treatment of diseases or disorders mediated by ATF6 and may find particular use in the treatment of viral infections, neurodegenerative diseases, vascular diseases, or cancer.

Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature

BF3·OEt2-mediated cross-coupling of (SnMe3)2 with aryl triazene offers a new strategy for the synthesis of aryl stannane. A variety of synthetically useful aryl trimethylstannanes were produced in moderate to good yields with this metal-free approach. One-pot sequential Stille cross-coupling with different aryl bromides provides a short entry to both symmetrical and unsymmetrical biaryl compounds.

Ligand-Induced Reductive Elimination of Ethane from Azopyridine Palladium Dimethyl Complexes

Reductive elimination (RE) is a critical step in many catalytic processes. The reductive elimination of unsaturated groups (aryl, vinyl and ethynyl) from Pd(II) species is considerably faster than RE of saturated alkyl groups. Pd(II) dimethyl complexes ligated by chelating diimine ligands are stable toward RE unless subjected to a thermal or redox stimulus. Herein, we report the spontaneous RE of ethane from (azpy)PdMe2 complexes and the unique role of the redox-active azopyridine (azpy) ligands in facilitating this reaction. The (azpy)PdMe2 complexes are air- and moisture-stable in the solid form, but they readily produce ethane upon dissolution in polar solvents at temperatures from 10 °C to room temperature without the need for an external oxidant or elevated temperatures. Experimental and computational studies indicate that a bimolecular methyl transfer precedes the reductive elimination step, where both steps are facilitated by the redox-active azopyridine ligand.

Cathode electrochromic compound for electrochromic device

An electrochromic medium comprises a cathode electrochromic compound, wherein the structural formula of the cathode electrochromic compound is as shown in the specification, R1 is selected from normal alkyl or heterogeneous alkyl containing 1-20 carbon atoms; each of R2-R14 is independently selected from H, alkyl, cycloalkyl, polycyclic alkyl, aryl, heterocyclic alkyl, aromatic alkyl and alkaryl containing 1-50 carbon atoms or alkyl, cycloalkyl, polycyclic alkyl, aryl, heterocyclic alkyl, aromatic alkyl and alkaryl containing 1-50 carbon atoms and halogen, N, O, S, Si, P or unsaturated bond groups; X1 is selected from acetate anion, methyl phenyl acetate sulfonate anion, tetrafluoroborate anion, hexafluoroborate anion, tetraphenyl borate anion, trifluoro mesylate anion, perchlorate anion, bis-oxalate borate anion, oxalate difluoroborate anion, bis(trifluoromesyl) imide anion and tri(trifluoromesyl) methyl anion. The cathode electrochromic compound has the advantages that good electrochemical reversibility is achieved, fast color changing and good stability are achieved, the lowest value of visible light transmittance is small, and the like.

Synthesis of aryl trimethylstannanes from aryl halides: An efficient photochemical method

An efficient transition-metal-free photochemical method featuring excellent functional group tolerance, mild reaction conditions and short reaction times has been discovered and developed for the synthesis of (hetero)aryl trimethylstannanes from (hetero)aryl halides. A photo-initiated radical chain mechanism was proposed based on preliminary mechanistic studies.

Thermal and Light-Induced Spin Transitions of FeII Complexes with 4- and 5-(Phenylazo)-2,2′-bipyridine Ligands: Intra- vs. Intermolecular Effects

Five new spin crossover complexes with 4- and 5-(phenylazo)-2,2-bipyridine (4-/5-PAbipy) ligands were synthesized and investigated with respect to their spin crossover (SCO) behavior. The results are compared to the thermal and light-induced spin transition properties of the parent SCO complexes [Fe(bpz)2(bipy)] (1) and [Fe(bipy)2(NCS)2] (2). [Fe(bpz)2(4-PAbipy)] (1a) undergoes a stepwise spin transition whereas [Fe(bpz)2(5-PAbipy)] (1b) exhibits a one-step transition with a 6 K-wide hysteresis. For [Fe(bpz)2(tBu5-PAbipy)] (1c) the spin transition to the low-spin state is incomplete. Qualitatively similar changes of the SCO behavior are observed for the complexes [Fe(4-PAbipy)2(NCS)2] (2a) and [Fe(5-PAbipy)2(NCS)2] (2b). In comparison to the parent system 2, a strengthening of intermolecular interactions leads to a stabilization of the low-spin state. Evidence for the LIESST behavior could be obtained for all new compounds by means of magnetic susceptibility measurements as well as UV/Vis and resonance Raman spectroscopy.

Selective synthesis of mono- and distannylpyridines from chloropyridinols via an SRN1 mechanism

A selective two-step synthesis of either mono- or distannylated pyridines from commercially available pyridinols, involving its conversion to the corresponding diethyl pyridyl phosphates (pyDEP) followed by the reaction with Me3SnNa in liquid ammonia, is described. The results obtained clearly indicate that the reactions proceed through an unimolecular radical nucleophilic substitution mechanism (SRN1) with intermediacy of a monosubstitution product.

Phenols as starting materials for the synthesis of arylstannanes via SRN11

Phenols are converted into aryl diethyl phosphate esters (ArDEP), which on reaction with sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia afford arylstannanes by the SRN1 mechanism. Thus, the photostimulated reaction of phenylDEP (3), (4-methoxyphenyl)DEP (4), (4-biphenyl)DEP (5), (1-naphthyl)DEP (6), (2-naphthyl)DEP (7), and 2- (34), 3- (32), and (4-pyridyl)DEP (35) with 1 leads to monostannylated product in fair to excellent yields (20-98%). Also, substrates containing two or three leaving groups react with 1 under irradiation, affording the corresponding di- or tristannylated aryl compounds. With tetraethyl m-phenylene bisphosphate (15), tetraethyl p-phenylene bisphosphate (21), (4-chlorophenyl)DEP (22), and 1,3,5-tris(diethylphospho)benzene (30), the di- or trisubstitution products 1,3-bis(trimethylstannyl)benzene (19) (79%), 1,4-bis(trimethylstannyl)benzene (23) (95 and 97%), and 1,3,5-tris(trimethylstannyl)benzene (31) (57%) are obtained, respectively. Also, the reaction of 6 and 7 with 2 leads to substitution products in quantitative yields, and the reaction of 21, 22, and (4-bromophenyl)DEP (24) with 2 affords 1,4-bis(triphenylstannyl)benzene (38) in high yields (70-100%). On the other hand, the results obtained in the photostimulated reaction of 24 and (4-iodophenyl)DEP (25) with 1, as well as in the reaction of 25 with 2, clearly indicate a fast HME reaction.