Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 74115-13-2, 5-Bromo-3-pyridinol, 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, 74115-13-2, blongs to pyridine-derivatives compound. Formula: C5H4BrNO

A mixture of 3-bromo-5-hydroxypyridine (At°rich, Buchs, Switzerland, 611 mg, 3.51 mmol), potassium carbonate (971 mg, 7.02 mmol) and 2-bromoethyl methyl ether (537 mg, 3.86 mmol) in 30 ml DMF was stirred for 14 h at rt and for 2 h at 80C The reaction mixture was quenched with water and extracted with EtOAc (2x). The organic layers were washed with brine (3x), dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (dichloromethane/MeOH 0% to 3%) to give the title compound as an oil (HPLC- tkappa 2.38 min (Method A), M+H = 232, 234 MS-ES)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74115-13-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 155601-65-3, 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 155601-65-3 as follows.

2,6-difluoronicotinaldehyde was obtained as described in M. Schlosser and T. Rausis, Eur. J. Org. Chem. 2004, 1018.A mixture of 2,6-difluoronicotinaldehyde (2 g, 13.9 mmol), 2-amino-5- methylphenol (1.7 g, 13.8 mmol) and 2,3-butanedione monoxime (1.065 g, 10.5 mmol) in acetic acid (120 mL) was heated at 120C for 1.5 hours. After cooling down to room temperature, zinc powder (2 g) was added and the mixture heated one hour at 120C and left overnight at room temperature. The suspension is then filtered and filtrate is reduced to about 20 mL. Water was added (about 100 mL) and aqueous KOH was added up to pH ~ 8. The mixture was extracted with dichloromethane and the crude obtained purified by column chromatography using CH2Cl2/Et20 as eluent. The ligand was obtained as a beige solid (2.14 g, yield 68 %).1H MR (CDC13, 400 MHz) : delta 8.28 (t, J= 8.0 Hz, IH) ; 7.25 (d, J= 1.6 Hz, IH) ; 7.09 (d, J= 8.4 Hz, IH) ; 6.99 (ddd, J= 8.0, 2.0, 0.8 Hz, IH) ; 6.79 (dd, J= 8.4, 2.8 Hz, IH) ; 2.27 (s, 3H) ; 2.24 (d, J= 0.8 Hz, 3H) ; 2.19 (d, J= 0.8 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,155601-65-3, its application will become more common.

Reference:
Patent; SOLVAY SA; NAZEERUDDIN, Mohammad Khaja; BARANOFF, Etienne David; GRAETZEL, Michael; WO2012/19948; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 131747-43-8, 2-Trifluoromethylnicotinic acid, 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, 131747-43-8, blongs to pyridine-derivatives compound. COA of Formula: C7H4F3NO2

Alternate coupling procedure:Combine 4-(4,5-dimethyl-6-(4-(methylamino)piperidin-l-yl)pyridazin-3- yl)benzonitrile (300 mg, 0.93 mmol), 2-(trifluoromethyl)nicotinic acid (210 mg, 1.12 mmol) and diisopropylethylamine (0.79 mL, 4.51 mmol) in a 4: 1 mixture of DMF and DMSO (20 mL). Heat the mixture briefly at 60 0C to dissolve the solids, and then cool to 0 0C. Add a solution of perfluorophenyl diphenylphosphinate (750 mg, 1.96 mmol) in a 4: 1 mixture of DMF and DMSO (1 mL) dropwise. Heat the resulting mixture at 60 0C overnight. Partition the reaction mixture between aqueous NaHCO3 solution and CH2Cl2. Wash the organic layer with brine, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the resulting residue by flash silica gel chromatography (20:5: 1 hexanes: EtOAc: 2 M NH3/MeOH) to provide the free base of the title compound (346 mg, 75%). ES/MS m/z 495.2 (M+l). Form the HCl salt as described above.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131747-43-8, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie, Anne; CLAY, Julia, Marie; COHEN, Jeffrey, Daniel; HIPSKIND, Philip, Arthur; LOBB, Karen, Lynn; SALL, Daniel, Jon; WILSON (NEE TAKAKUWA), Takako; THOMPSON, Michelle, Lee; WO2010/56588; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1137-68-4, Adding some certain compound to certain chemical reactions, such as: 1137-68-4, name is 2-(2-Pyridyl)benzimidazole,molecular formula is C12H9N3, 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 1137-68-4.

EXAMPLE 9 To a solution of (2S)-N-[4-(5-bromopentyl)oxy-5-methoxy-2-nitrobenzoyl) pyrrolidine-2-carboxarbaldehyde diethyl thioacetal 2c (549 mg, 1 mmol) in dry DMF (10 ml_) was added anhydrous K2CO3 (552 mg, 4 mmol) and the 2-(2- pyridyl)benzimidazole 4a (195 mg, 1 mmol). The reaction mixture was stirred at room temperature for 48 h. TLC using ethyl acetate as a solvent system monitored the reaction. The potassium carbonate was removed by suction filtration and the solvent was removed under vacuum. The crude product was purified by column chromatography using 2% MeOH-CHCI3 as eluent to afford pure compound of 9b (498 mg, 75%). 1H NMR (CDCI3): 8.62 (d, J = 5.1 Hz, 1 H), 8.44 (d, J = 8.0 Hz, 1 H), 7.75-7.87 (m, 2H), 7.47-7.51 (m, 1 H), 7.45 (s, 1H), 7.20-7.35 (m, 3H), 6.77 (s, 1 H), 4.82 (d, J = 3.7 Hz, 1 H), 4.57-4.71 (m, 3H), 4.02-4.15 (m, 2H), 3.97 (s, 3H), 3.10-3.30 (m, 1 H), 2.90-3.08 (m, 1 H), 2.65-2.85 (m, 4H), 2.45-2.62 (m, 2H), 1.60-2.40 (m, 6H), 1.44-1.50 (m, 2H), 1.30-1.42 (m, 6H) ESIMS: m/z 666 (M+).

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. 1137-68-4, 2-(2-Pyridyl)benzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; WO2009/113085; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 407-20-5, 3-Bromo-5-fluoropyridine, 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, 407-20-5, blongs to pyridine-derivatives compound. Recommanded Product: 407-20-5

To a solution of diisopropylamine (6.899 g, 9.555 mL, 68.18 mmol) in THF (75 mL) cooled to -78C, was added butyllithium (25 mL of 2.5 M in hexanes, 62.5 mmol). The reaction mixture was allowed to warm to -20C then cooled back down to -78C. A solution of 3-bromo-5-fluoro-pyridine (10 g, 56.82 mmol) in THF (25 mL) was added dropwise keeping temperature below -70C (approx 30 mins). The reaction mixture was stirred at – 78C for 30 mm and a solution of 1,1,1,2,2,2-hexachloroethane (14.8 g, 62.5 mmol) in THF (20 mL) was then added dropwise, keeping temperature below -70C (over approx 30 mins). The mixture was stirred at -78C for 20 minutes, allowed to warm to room temperature, cooled back to 0C and quenched with water (100 mL). EtOAc (400 mL) was then added, and organic layer separated, washed with water (2x), brine (lx), dried (Mg504), filtered and concentrated in vacuo to leave a brown solid. The solid was triturated in pentane (lOOmL) for 10 minutes, then filtered. The filtrate was concentrated in vacuo to afford product as a brown oil that turned to a crystalline solid on standing, 11.85 g, 89%). ?H NMR (DMSO-d6) oe 8.78 (s, 1H), 8.76 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,407-20-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BOYALL, Dean; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; ETXEBARRIA I JARDI, Gorka; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PINDER, Joanne; WO2015/84384; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6304-16-1 , The common heterocyclic compound, 6304-16-1, name is (4-Pyridyl)acetone, molecular formula is C8H9NO, 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.

EXAMPLE 41 2-[(Aminocarbonyl)amino]-4-methyl-5-(4-pyridyl)-3-thiophenecarboxamide Prepared by the method of Example 26 from (4-pyridyl)acetone. MS (ES) 275 (M-H)-. 1H NMR (DMSO-D6) 8.55 (2H, m), 7.2 (4H, m), 7.1 (2H, m), 2.35 (3H, s).

The synthetic route of 6304-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baxter, Andrew; Brough, Stephen; Faull, Alan; Johnstone, Craig; McInally, Thomas; US2002/107252; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866546-07-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 866546-07-8, name is 5-Chloro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

To 5-chloro-lH-pyrrolo[2,3-]rhoyridine (10.0 g, 65.6 mmol) in EtOAc (70 mL) at 0 C was added dropwise over 15 h a solution of m-chloroperbenzoic acid (57%, 17.9 g,104 mmol) in EtOAc (80 mL). The reaction mixture was stirred for 20 h at RT. Then, the mixture was cooled to -40C and the solids were filtered off and rinsed with cold EtOAc. The solid was taken up in water (70 mL) and treated dropwise with 30% aq. K2CO3 until pEta was 11. The solution was warmed for 30 min, cooled to 0 0C, filtered and dried in vacuo. Analysis (NMR) indicated the presence of m- chloroperbenzoic acid. The solid was taken up in 10% MeOH in DCM and washed with EPO 30% aq. K2CO3 until all m-chlorobenzoic acid was removed. The organic layer was dried over Na2SO4, filtered and concentrated to provide 2.61 g (24% yield) of 5-chloro-lH- pyrrolo[2,3-b]pyridine-iV-oxide (C). The combined mother liquors were concentrated. Flash chromatography (5% MeOEta- DCM) provided and additional 1.49 g (13% yield) contaminated with -10 % of the benzoic acid. LC/MS (M + H+) 168.76.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/127587; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1597-33-7, name is 2-Fluoropyridin-3-amine, molecular formula is C5H5FN2, molecular weight is 112.11, as common compound, the synthetic route is as follows.SDS of cas: 1597-33-7

To a solution of the corresponding amines (1 equiv.) in dichloromethane was added pyridine (1 equiv.) and phenyl chloroformate (1 equiv.) at 0 C. Stirring was continued for 2 h followed by the addition of the scaffold amine (1 equiv.) and DMAP (0.2 equiv.). The reaction mixture was refluxed overnight. After cooling, water was added and extracted with dichloromethane. The pooled organic fractions were brine washed, dried, concentrated and purified by Reverse Phase Prep-HPLC to provide compounds A6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1597-33-7, 2-Fluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; POPOVICI-MULLER, Janeta; SALITURO, Francesco Gerald; SAUNDERS, Jeffrey Owen; TRAVINS, Jeremy; YAN, Shunqi; WO2014/62511; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14150-94-8, Adding some certain compound to certain chemical reactions, such as: 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one,molecular formula is C6H5N3O5, 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 14150-94-8.

A mixture ofbenzyl (3-oxocyclohexyl)carbamate (247 mg, 0.999 mmol) and 1-methyl- 3,5-dinitropyridin-2(1H)-one (300 mg, 1.507 mmol) in ammonia/MeOH (1M, 6 mL) was microwaved at 90 C for 30 mm to provide a blackish-red solution. Eleven more samples of the same composition were run under the same conditions. The twelve samples were combined and evaporated under reduced pressure. The residue was partitioned between DCM (300 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 50% EtOAc in hexanes) provided a mixture of benzyl (3-nitro- 5,6,7, 8-tetrahydroquinolin-7-yl)carbamate and undesired regioi somer benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-5-yl)carbamate as a pale yellow gum. The mixture was used without further purification. MS (ESI, m/z): 213 [M+H]t; j00424J A solution of benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (2.64 g, 8.07 mmol) in ethanol (110 mL) was treated with tin(II) chloride dihydrate (9.10 g, 40.3 mmol) and conc. HC1 (1 mL), then stirred at 80 C for 75 mm. The solution was allowed to cool, then was concentrated under reduced pressure to about 15 mL. The sample was made basic (pH 9) by addition of saturated aqueous NaHCO3; about midway through, the sample was diluted with DCM (100 mL). The mixture was triturated, then filtered, and the filter cake was washed with DCM (50 mL). The filter cake was triturated and sonicated in MeOH (200 mL), then the mixture was filtered. The slightly cloudy filtrate was filtered through Celite 545, then concentrated to provide a yellow solid. Purification by silica gel chromatography (0 to 15% MeOH in DCM) provided a mixture of benzyl (3-amino-5,6,7,8-tetrahydroquinolin-7-yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification. MS (ESI, m/z):298 [M+H]t; 1004251 A sample of benzyl (3-amino-S ,6, 7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (1.25 g, 4.22 mmol) was treated with ACN (17 mL). The material was cooled on a dry ice / ethylene glycol bath (approximately -10 to -15 C) and PTSA monohydrate (1.61 g, 8.45 mmol) was added. After stirring 10 mm, a solution of potassium iodide (1.05 g, 6.33 mmol) and sodium nitrite (0.436 g, 6.32 mmol) in water (3.4 mL) was added dropwise over 20 mm. The dry ice bath was replaced with an ice bath, and the reddish-brown mixture was stirred at 0 C for 3 h 40 mm. The solution was diluted with EtOAc (50 mL), cooled on an ice bath and treated with saturated aqueous NaHCO3 until basic (pH 8-9). The organic layer was removed and the aqueous layer was extracted once more with EtOAc (50 mL). The combined organics were washed sequentially with water and brine (50 mL each), dried (Na2504), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 23% EtOAc in hexanes) provided a mixture of benzyl (3-iodo-S,6,7,8-tetrahydroquinolin-7- yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification.MS (ESI, m/z): 409 [M+H]; 1004261 A mixture of t-BuXPhos Pd G4 (76.3 mg, 94.4 tmole), benzyl (3-iodo-5,6,7,8- tetrahydroquinolin-7-yl)carbamate and regioisomer (605.0 mg, 1.482 mmol), tert-butyl piperazine-1-carboxylate (553.5 mg, 2.97 mmol), and sodium tert-butoxide (257.1 mg, 2.68 mmol) was sealed in a 40-mL vial. The atmosphere was evacuated and replaced with nitrogen, three times. Dioxane (15 mL) was added and the solution was stirred at ambient temperature for three days. Material at the same stage from a previous run (from 40.7 mg, 0.100 mmol iodo starting material) was added. The mixture was diluted with EtOAc (100 mL), treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 87% EtOAc in hexanes) provided a mixture of tert-butyl 4-(7-(((benzyloxy)carbonyl)amino)-5 ,6,7, 8-tetrahydroquinolin-3 – yl)piperazine-1-carboxylate and regioisomer as a yellow foam. The mixture was used without further purification. MS (ESI, m/z): 467 [M+H].

According to the analysis of related databases, 14150-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 82671-06-5, 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 82671-06-5 as follows.

Example 16A (^-Sjdelta-Difluoro^-hydroxy^^i^Kfl.SloxathioIoS^-clpyridin-theta- ylmethyl)amino]-l-piperidinyl}methyI)-4,5-dihydro-7H-pyrrolo[3,2,l-^]-l?5- naphthyridin-7-one dihydrochloride(a) 2-Chloro-5-fluoro-6-(methyloxy)-3-pyridinecarboxylic acidA solution of 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (51.12g, 243 mmol) in methanol (400 ml) was treated with sodium methoxide in methanol (25% w/v, 100 ml, 535 mmol) and the mixture heated to reflux for 4 hours. The cooled mixture was treated with water (400 ml) and acidified to pH2 with aqueous hydrochloric acid (2M) then concentrated to ca 400 ml. Filtration, washing with water and drying in vacuo over P2O5 for 18h afforded the product as a white solid (32.65g, 65%). MS (+ve ion electrospray) m/z 208 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,82671-06-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/71936; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem