Day: April 20, 2022

Related Products of 117846-58-9 , The common heterocyclic compound, 117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 1: 2-(4-(6-Bromo-3,5-dimethylpyridin-2-ylamino)piperidin-1-yl)benzonitrile A mixture of 2-(4-amino-1-piperidyl)benzonitrile (3.00 g, 14.91 mmol), 2,6-dibromo-3,5-dimethyl-pyridine (4.74 g, 17.89 mmol), tBuONa (2.15 g, 22.36 mmol), Pd2 (dba)3 (136.53 mg, 149.05 umol) and BINAP (278.43 mg, 447.16 umol) in toluene (50.00 mL) was stirred at 80 C. for 17 h. The mixture was filtered and purified by silica gel chromatography to afford 2-(4-(6-bromo-3,5-dimethylpyridin-2-ylamino)piperidin-1-yl)benzonitrile (2.10 g, 5.45 mmol, 36.55% yield) as product. ESI-MS (EI+, m/z): 385.1 [M+H]+.

The synthetic route of 117846-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. category: pyridine-derivatives

(b). 2,3-dimethoxypyridine To a solution of 2-chloro-3-methoxy-pyridine (1 10 g) in DMSO (1 L) was added sodium methoxide (124 g). The reaction mixture was heated to 80C overnight. The reaction mixture was poured into 3 L water and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product. Yield: 105 g ? NMR delta (ppm)(CH3OH-d): 7.70 (t, 1 H, J=1.2 and 5.2 Hz), 7.01 (t, 1 H, J=1.2 and 8.0 Hz), 6.81 (q, 1 H, J=5.2 and 7.8 Hz), 4.00 (s, 3H), 3.85 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 52605-96-6.

Reference:
Patent; MSD OSS B.V.; BLACKABY, Wesley, Peter; DE KORT, Martin; ENTHOVEN, Mark; HINCHLIFFE, Paul, Stuart; PAULIE, Chris; TIMMERS, Cornelis, Marius; VERKAIK, Saskia; WO2013/41458; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1227573-02-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1227573-02-5, name is 3-Bromo-5-fluoroisonicotinaldehyde, molecular formula is C6H3BrFNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 3-bromo-5-fluoroisonicotinaldehyde (0.656 g, 3.22 mmol) in THF (5 mL) was added prop-1-yn-1-ylmagnesium bromide (0.5 M in THF, 8.36 mL, 4.18 mmol) solution at 0 C. After stirring at 0 C. for 2 h, excess sat. aq. NaHCO3 solution was added to quench the reaction mixture followed by extracting with EtOAc twice and DCM twice. All organic layers were combined and dried over anhydrous Na2SO4. The solid was filtered out. Volatiles were removed under reduced pressure to afford the title compound (0.78 g, 99%). It was used directly in the next step without further purification. ESI-MS m/z: 245.9 [M+H]+ (Rt=0.92 min., LC-method 3)

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1227573-02-5, 3-Bromo-5-fluoroisonicotinaldehyde.

Reference:
Patent; NOVARTIS AG; BARBE, Guillaume; BEBERNITZ, Gregory Raymond; GENG, Sicong; GULGEZE EFTHYMIOU, Hatice Belgin; LIAO, Lv; MA, Fupeng; MO, Ruowei; PARKER, David Thomas; PENG, Yunshan; PEUKERT, Stefan; YAMADA, Ken; YASOSHIMA, Kayo; (78 pag.)US2018/111932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5453-67-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 5453-67-8 as follows.

Step 1: Preparation of methyl 6-formylpyridine-2-carboxylate (I-33a) A suspension of dimethylpyridine-2,6-dicarboxylate (1.0 g, 5.12 mmol) in methanol (8 mL) and THF (3 mL) was heated at 75 C. until the solid was dissolved. NaBH4 (184 mg, 4.87 mmol) was then added portion-wise. The mixture was stirred at 70 C. for 1 h. The mixture was cooled to room temperature and 10% citric acid (1.6 mL) was added. The solution was filtered and the filtrate was evaporated to dryness, taken up in dichloromethane, dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-100% EtOAc in isohexane, to provide a colourless oil which was then dissolved in toluene (20 mL) and chloroform (20 mL). MnO2 (194 mg, 22.2 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was filtered through a pad of fluorosil, eluting with chloroform (30 mL) and the solvent was removed in vacuo to provide the title compound (249 mg, 29%) as white solid. 1H NMR (400 MHz, CDCl3): delta 10.20 (s, 1H), 8.37 (dd, J=1.2, 7.6 Hz, 1H), 8.17 (dd, J=1.2, 7.6 Hz, 1H), 8.08-8.04 (m, 1H), 4.07 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5453-67-8, its application will become more common.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; GHIDINI, Eleonora; BAKER-GLENN, Charles; VAN DE POEL, Herve; WHITTAKER, Ben; US2015/158858; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 92276-38-5, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3BrN4

To a suspension of NaH (60% in mineral oil, 120 mg, 3.0 mmol) in THF (3 mL) at 0C was added 6-bromo-1 H-[1 ,2,3]triazolo[4,5-£>]pyridine (400 mg, 2.0 mmol) in THF (8 mL). The mixture was stirred at 0C for 30 min, then SEM-CI (500 mg, 3.0 mmol) was added at 0C dropwise and stirring was continued for 1 h. The reaction was quenched with NH4CI (sat.) and extracted with EtOAc (3 x 20 mL). The organic layers were combined and washed with brine (2 x 20 mL), dried over Na2S04, concentrated and purified by chromatography to give lnt-6-11 as a mixture of 6- bromo-1 -((2-(trimethylsilyl)ethoxy)methyl)-1 H-[ ,2,3]triazolo[4,5-i>]pyridine and 6-bromo-3-((2- (trimethylsilyl)ethoxy)methyl)-3H-[1 ,2,3]triazolo[4,5- ?]pyridine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92276-38-5, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; SCHMITT, Aaron C.; GEGE, Christian; (205 pag.)WO2016/96115; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1111637-94-5 , The common heterocyclic compound, 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A solution of 19 (100 mg, 0.434 mmol) and 52 (118.2 mg, 0.434 mmol) in toluene/ ethanol (4:1) was added sodium carbonate (95.04 mg, 0.868 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (17.72 mg, 0.0217 mmol) was added to the reaction. The reaction mass was degassed and purged with nitrogen for another 10 min. The reaction was heated to 80 C. under sealed condition overnight. The reaction was allowed to cool to rt and diluted with chloroform. The organic layer was filtered through Celite bed and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 2% methanol in chloroform as off-white colour solid compound 53. MS-ES+ 277.9; 1H NMR (400 MHz, DMSO-D6) 53: 11.31 (s, 1H), 9.46 (s, 1H), 8.12 (d, 1H), 7.83 (d, 1H), 7.56 (d, 1H), 7.33 (m, 4H), 7.24 (bs, 1H), 6.30 (m, 1H), 6.11 (m, 1H), 5.62 (m, 1H), 2.22 (s, 3H).

The synthetic route of 1111637-94-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 188577-68-6, 4,5-Dichloropyridin-2-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 188577-68-6, blongs to pyridine-derivatives compound. Product Details of 188577-68-6

4,5-Dichloropyridin-2-amine (INTERMEDIATE 1, 45.2 g, 283.0 mmol) was added to 270 mL of ice cold conc. H2SO4, in small portions over ca 20 min. When dissolved, conc. HNO3 (22 g) was added dropwise and the mixture was stirred at ca 5 C for 3.5 h. LCMS indicated total conversion to expected product. The cold mixture was poured on crushed ice/water mixture (3 L), stirred for ca 5 min and then filtered. The solid was collected and slurried in ice cold water (500 mL) and filtered. The procedure was repeated until neutral pH. When semi dry on the filter, the solid was dissolved in EtOAc (ca.3 L), washed with brine (ca.100 mL) and the organic layer was dried with Na2SO4, filtered, and evaporated to furnish 46.2 g (78%) of 97% pure title product as beige-orange solid.1H NMR (600 MHz, CD3OD) delta^D) delta (600 MHz, CDaporated to furnish 46.2+) m/z 208, 210, 212 [M+H]+ , di-chlorine isotopic pattern.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,188577-68-6, 4,5-Dichloropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; KANCERA AB; MELLSTEDT, Hakan; BYSTROeM, Styrbjoern; VAGBERG, Jan; OLSSON, Elisabeth; (302 pag.)WO2018/11138; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138.55, as common compound, the synthetic route is as follows.

A mixture of [1,] [2-DIAMINO-2-METHYLPROPANE] [(3.] 14ml, [30] [MMOL),] and 6- chloronicotinonitrile [(2.] [77G,] [20] mmol) were heated to [120 C] for 2 days. The reaction mixture was filtered, and the inorganic salt was rinsed with EtOAc. The filtrate was concentrated under reduced pressure to provide the titled compound as a pale yellow solid. MS [(DCI)] [191] 1 9 1 [(M+H)] [+.]

The chemical industry reduces the impact on the environment during synthesis 33252-28-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67625-36-9, Ethyl 5-chloroimidazo[1,2-a]pyridine-2-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 67625-36-9, blongs to pyridine-derivatives compound. Recommanded Product: 67625-36-9

Example 45-Methoxy-imidazo[1 ,2-a]pyridine-2-carboxylic acid [5-(3-trifluoromethyl-phenyl)-1 H- benzoimidazol-2-yl]-amide To a stirring solution of 5-chloro-imidazo[1 ,2-a]pyridine-2-carboxylic acid ethyl ester(674 mg) in dry THF (5 mL) was added sodium methoxide (324 mg), and the reaction mixture was heated to 50 C for 1 hour. The resulting mixture was cooled to room temperature, quenched with ice, and partitioned between ethyl acetate and water. The organic layers were evaporated and the resulting crude intermediate was hydrolyzed with lithium hydroxide (1.3 g) in 1 :1 methanol/water (10 mL) by heating to 100 C for 0.5 hour. The resulting mixture was partitioned between ethyl acetate and water, and the organic layers were evaporated to give a solid, which was dissolved in DMF (5 mL), to which was added 5-(3-trifluoromethyl-phenyl)-1 H-benzoimidazol-2-ylamine dihydrobromide salt (878 mg), HBTU (760 mg) and DIEA (0.70 mL). The resulting mixture was heated to 90 0C for 1 hour then cooled to room temperature. Water was added and the resulting solid was filtered, dried and purified by silica gel flash chromatography using 10% of MeOH in DCM to obtain the title compound (311 mg). LCMS (m/z): 452.9. 1H NMR (400 MHz, CD3OD): delta 3.58 (3H, S)1 7.43 (1 H, d), 7.68-8.05 (9H, m), 9.17 (1 H, s) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67625-36-9, its application will become more common.

Reference:
Patent; HIGH POINT PHARMACEUTICALS, LLC; MJALLI, Adnan, M.M.; HARI, Anitha; GADDAM, Bapu; GOHIMUKKULA, Devi, Reddy; POLISETTI, Dharma, R.; EL ABDELLAOUI, Hassan; RAO, Mohan; ANDREWS, Robert, C.; XIE, Rongyuan; REN, Tan; WO2010/126745; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1035219-96-5, name is 2-Bromo-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of intermediate 6 (2.33 g, 10 mmol), phenylacetylene (2.0 g, 20 mmol) and triethylamine (4.5 g, 45 mmol) in 1,4-dioxane (50 mL) at room temperature were added [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.73 g, 1 mmol) and copper (I) iodide (0.75 g, 4 mmol) under a nitrogen atmosphere. The reaction mixture was stirred at 80 C. for 2 hours under a nitrogen atmosphere, then cooled to room temperature and concentrated in vacuo. The resulting residue was dissolved in AcOEt and washed with H2O. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; petroleum ether/AcOEt 10:1 to 1:1). The desired fractions were collected and the solvent was evaporated in vacuo to yield compound 3 (0.7 g, 30% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.00 (t, J=7.0 Hz, 2H), 3.50 (td, J=7.0, 2.5 Hz, 2H), 7.44-7.57 (m, 3H), 7.63-7.72 (m, 2H), 8.07 (br. s., 1H).

The synthetic route of 1035219-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica N.V.; US2012/252800; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem