Category: pyridine-derivatives

Electric Literature of 1221171-88-5 ,Some common heterocyclic compound, 1221171-88-5, molecular formula is C6H5F3N2O, 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.

The product of Example 158B (62 mg, 0.11 mmol) and (1509) bis(tetramethylene)fluoroformamidinium hexafluorophosphate (50 mg, 0.16 mmol, Alfa) were charged to a sealed tube, and a solvent mixture of dichloromethane (0.26 mL) and N,N- diisopropylethylamine (0.083 mL, 0.47 mmol) was added in one portion. The resulting mixture was stirred at ambient temperature for 30 minutes and 5-(trifluoromethoxy)pyridin-2-amine (22.5 mg, 0.13 mmol, Astatech) was added. The tube was sealed and stirred at 75 C for 18 hours. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (3 mL), filtered through a glass microfiber frit and purified by preparative HPLC [YMC TriArt CI 8 Hybrid 5 mupiiota column, 50 x 100 mm, flow rate 70 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (12 mg, 0.023 mmol, 22% yield). JH NMR (400 MHz, DMSO-<) ppm 9.95 (s, 1H), 8.39 - 8.36 (m, 1H), 8.11 (dd, J = 9.2, 0.6 Hz, 1H), 7.83 (ddd, J = 9.2, 3.0, 1.0 Hz, 1H), 7.48 - 7.41 (m, 2H), 7.00 (dd, J = 11.4, 2.8 Hz, 1H), 6.78 (ddd, J = 9.0, 2.8, 1.2 Hz, 1H), 4.42 (s, 2H), 1.92 - 1.78 (m, 12H). MS (APCI+) m/z 516 (M+H)+. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221171-88-5, its application will become more common. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 885588-17-0, Adding some certain compound to certain chemical reactions, such as: 885588-17-0, name is 5-Fluoro-2-methylisonicotinic acid,molecular formula is C7H6FNO2, 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 885588-17-0.

To a mixture of 5-fluoro-2-methylisonicotinic acid (200 mg) in dichloromethane (7 ml) und DMF (1 ml) was subsequently added at 22 C EDCI (198 mg), HOBT (158 mg) and triethylamine (163 mg) and stirring was continued for 15 min. l,3,3-Trimethyl-2-oxoindoline-6- carbohydrazide (165 mg) was added and stirring was continued for 18 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 10% MeOH in dichloromethane) to give the title compound (186 mg, 62%) as yellow oil. MS (ESI, m/z): 371.1 [(M+H)+].

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 885588-17-0, 5-Fluoro-2-methylisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56946-65-7, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[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, 56946-65-7, blongs to pyridine-derivatives compound. HPLC of Formula: C8H7Cl2N

To a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[Z?]pyridine (0.152 g, 0.81 mmol) in dioxane (3 mL) was added 2-(tributylstannyl)oxazole (0.318 g, 0.89 mmol) and tetrakis(triphenylphosphine)palladium (0.046 g, 0.040 mmol). The mixture was purged with nitrogen and then heated to 110 C under sealed conditions for 16 h. After this time, the mixture was diluted with water and extracted with ethyl acetate. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.061 g, 34%) as a white solid. MW = 220.66. ]H NMR (CDC13, 500 MHz) delta 7.94 (s, 1H), 7.78 (s, 1H), 7.29 (s, 1H), 3.19 (t, / = 7.5 Hz, 2H), 3.06 (t, / = 7.5 Hz, 2H), 2.22 (quin, J = 7.5 Hz, 2H); APCI MS m/z 221 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56946-65-7, its application will become more common.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

Step-1: Preparation of 2-(2,6-Bis-benzyloxy-pyridin-3-yl)-2,6-dihydro-4H-pyrrolo[3,4- c]pyrazole-5-carboxylic acid tert-butyl ester (26-2) (1327) (1328) Compound 26-2 was synthesized according to Scheme 26. Yield: 12%; LC MS: ES+ 499.3.

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; CHEN, Chi-li; DUPLESSIS, Martin; HE, Minsheng; LAZARSKI, Kiel; (980 pag.)WO2017/197051; (2017); A1;,
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Pyridine | C5H5N – PubChem

Reference of 57883-25-7 ,Some common heterocyclic compound, 57883-25-7, molecular formula is C7H8BrNO, 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.

To a solution of 3-bromo-2-ethoxy-pyridine (350 mg, 1.7 mmol) in NMP (2 mL) was added Zn(CN)2 (244 mg, 2.1 mmol) and Pd(dppf)C12 (127 mg, 0.17 mmol). The mixture was degassed with N2 and heated at 140C under microwave irradiation for 1 hour. The mixture was cooled to roomtemperature and filtered through celite. The filtered cake was washed with ethyl acetate (30 mL). The filtrate was washed with water (20 mL x 2) and brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (0%20% ethyl acetate in petroleum ether) to give 2-ethoxynicotinonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57883-25-7, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); 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

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;,
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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: 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 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