Category: pyridine-derivatives

Electric Literature of 67367-26-4 ,Some common heterocyclic compound, 67367-26-4, molecular formula is C8H9NO3, 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.

In a 250 mL dry round bottom flask with a reflux condenser and magnetic stirrer was placed with 2-chloro-3-ethyl nicotinate (12.0 g, 64.7 mmol) in dry methanol (200 mL), and CH3ONa (21 mL, 97.0 mmol, 25% in methanol) were added slowly and the reaction mixture was refluxed for 16 hour. The reaction mixture was cooled to room temperature and quenched by addition of a saturated aqueous NH4CI solution and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give 2-methoxy-3-methyl nicotinate (10.0 g, 93%). In a dry 500 mL round bottom flask NaH (549 mg, 13.7 mmol, 60% in mineral oil) was added in DMF (10 mL). Acetophenone (1.5 g, 12.5 mmol) in dry DMF (10 mL) was added drop-wise at O0C in 30 min. The reaction mixture was stirred for 1 h at room temperature. 2- Methoxy-3-m ethyl nicotinate (2.08 g, 12.5 mmol) dissolved into dry DMF (10 mL) was added slowly on cooling. After addition the mixture was stirred for 16 h at EPO room temperature. The reaction mixture was quenched by addition of a saturated aqueous NH4CI solution and diluted with water. The solid was filtered off, washed with water and dried to give the diketo product (2.94 g, 92%). Poly phosphoric acid (15.0 g) was heated at 9O0C and the diketo compound (1.5 g, 3.50 mmol) was added slowly and heated at 9O0C for 1 hours. The reaction mixture was cooled to room temperature and diluted with water. The solid was separated by filtration, washed with water and dried to give pure 2-phenyl-4H-pyrano[2,3- b]pyridin-4-one (655 mg, 50%); MS (ES) m/z: 224.94 (M+1 ), 223.95 (M); MP 103- 1050C

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67367-26-4, its application will become more common.

Reference:
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13362-78-2, (E)-1,2-Di(pyridin-4-yl)ethene, 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, Formula: C12H10N2, blongs to pyridine-derivatives compound. Formula: C12H10N2

A mixture of Zn(NO3)26H2O (0.3 g, 1 mmol), H3tris (0.24 g,2 mmol), and bis(4-pyridyl)ethylene (0.18 g, 1 mmol) inmethanol (20 mL) was sealed in a Teflon-lined stainless steelcontainer and heated at 110 C for 30 hours, then slowlycooled to room temperature. The resulted yellow crystals werewashed with methanol and dried in air. Yield: 68percent.

The synthetic route of 13362-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cucos, Andrei; Paraschiv, Carmen; Shova, Sergiu; Madalan, Augustin; Sbarcea, Gabriela; Marinescu, Virgil; Andruh, Marius; Revue Roumaine de Chimie; vol. 60; 10; (2015); p. 1005 – 1013;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 112110-16-4, 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.112110-16-4, name is Dimethyl 5-methylpyridine-2,3-dicarboxylate, molecular formula is C10H11NO4, molecular weight is 209.2, as common compound, the synthetic route is as follows.

EXAMPLE 4 Preparation of 5-Methyl-2,3-pyridinedicarboxylic acid using hydrochloric acid A stirred mixture of 5-methyl-2,3-pyridinedicarboxylic acid dimethyl ester (20.9 g, 0.1 mol), hydrochloric acid (18.2 g, 0.5 mol) and water (72 g) is heated at 70 to 110 C. A mixture of methanol and water and hydrochloric acid is continuously distilled from the reaction mixture and heating is continued until the reaction is complete by chromatographic analysis. The reaction mixture is concentrated in vacuo and diluted with water. The title product is isolated by filtration, washed with water (30 mL) and dried in vacuo. The title product is identified by 1 H-NMR and mass spectroscopy and analyzed by high pressure liquid chromatography to be >96% pure.

Statistics shows that 112110-16-4 is playing an increasingly important role. we look forward to future research findings about Dimethyl 5-methylpyridine-2,3-dicarboxylate.

Reference:
Patent; American Cyanamid Company; US5122608; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1101120-05-1, 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, 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, Formula: C9H5N3O, blongs to pyridine-derivatives compound. Formula: C9H5N3O

General procedure: A solution of the aldehyde or ketone (1 equiv) and 2-methyl-5-nitrobenzenesulfonohydrazide (1.1 equiv) in MeOH (5 mL) was refluxed for 18 h unless otherwise stated. After cooling to room temperature, the precipitated solid was filtered off, washed with a little MeOH and dried.

The synthetic route of 1101120-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 960298-00-4, 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. 960298-00-4, name is 2-(Benzyloxy)-4-bromopyridine, molecular formula is C12H10BrNO, 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.

Step 2: mc-tert-butyl O£4i?V4-r2-(benzyloxy)pyridin-4-yl1-3-alphacvclopropyP-(2- methoxyethoxyV 5-(3 -methoxypropyDbenzyl] amino ) carbonylM-hydroxypiperidine- 1 – carboxylate; To a solution of the title compound from step 1 (1.47 eq.) in THF (0.3 M) at -78 0C was added n-BuLi (2.5 M in hexanes, 1.6 eq.). The resulting solution was stirred at -78 0C for 30 min. MgBr2 (0.5 M in Et2O, 1.9 eq.) was added, and the resulting solution was stirred at -78 0C for 30 min. A solution of ketoamide 3.1 (0.1 M in THF, 1 eq.) was added, and the reaction mixture warmed to rt over 16 h, quenched with NaHCO3 (aq., sat.), extracted with 2 x EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by automated flash chromatography (SiO2; 10- 80% EtOAc in hexanes) to afford the title compound as a clear, colorless oil.

According to the analysis of related databases, 960298-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/70869; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 571189-16-7 ,Some common heterocyclic compound, 571189-16-7, molecular formula is C14H20N4O4, 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 the reaction flask was added compound 39 (5.65 g, 18.34 mmol)Soluble in methanol,0.5 g Pd / C was added,Catalytic hydrogenation at room temperature,TLC tracking, to be completely complete,Diatomaceous earth, the solvent was removed by distillation under reduced pressure,To obtain a crude solid,And then petroleum ether: ether (30: 1) beating to get pink powder,4.75 g of compound 7-10 was obtained by drying,Yield: 93.1%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571189-16-7, its application will become more common.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Gao Yong; Ren Jing; Wang Qinglin; Wang Zhao; (67 pag.)CN106905245; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59782-85-3, 2,5-Dichloronicotinic 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, Formula: C6H3Cl2NO2, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO2

Description 97: methyl 4-(1-(2,5-dichloronicotinamido)cyclopropyl)benzoate (D97)To a solution of 2,5-dichloronicotinic acid (1 .84g, 7.06 mmol) in dry dimethylformamide (15ml) 1 -Hydroxybenzotriazole hydrate (1 .08 g, 7.06 mmol) and 1 -ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.03g, 10.58 mmol), a solution of methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (1 .67g, 7.06 mmol) and triethylamine (0.98ml, 7.06 mmol) in dry dimethylformamide (15ml) was added and the resulting mixture was stirred 1 h at room temperature. NH4CI saturated solution (50ml) was added the mixture was extracted with ethylacetate (3x50ml). Collected organics, after solvent evaporation, was purified by Biotage column SNAP-Si (50g) eluting with a mixture dichloromethane/ ethylacetate from 100/0 to 95:5. Collected organics after solvent evaporation afforded the title compound (D97) (1 .03 mg)MS: (ES/+) m/z: 365.1 [MH+] C17H14CI2N203 requires 364.41 H NMR (400MHz ,CHLOROFORM-d) delta = 8.46 (d, J = 2.4 Hz, 1 H), 8.14 (d, J = 2.4 Hz, 1 H), 8.05 – 7.99 (m, 2 H), 7.41 – 7.35 (m, 2 H), 7.17 (s, 1 H), 3.93 (s, 3 H), 1 .50 (s, 4 H).

The synthetic route of 59782-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); 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.13143-47-0, name is 1-(4-Aminophenyl)-1H-pyridin-2-one, molecular formula is C11H10N2O, molecular weight is 186.21, as common compound, the synthetic route is as follows.Quality Control of 1-(4-Aminophenyl)-1H-pyridin-2-one

Step 2: To a solution of compound 12.2 (7.44 g, 40 mmol) in 100 mL DMF was added NBS(14.2 g, 80 mmol) in small portions. The mixture was stirred at RT overnight. It was diluted with 1000 mL ethyl acetate, washed with brine three times, dried, concentrated and subjected to flash column chromatography using 5 % methanol in DCM to isolate compound 12.3 (7.20 g, 68 %). MS found for C11H9BrN2O (M+H)+ 265.0, 267.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13143-47-0, 1-(4-Aminophenyl)-1H-pyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; SCARBOROUGH, Carroll; WO2008/86226; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-22-1, 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.884495-22-1, name is 5-Bromo-2-fluoropyridin-3-amine, molecular formula is C5H4BrFN2, molecular weight is 191.0011, as common compound, the synthetic route is as follows.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

The chemical industry reduces the impact on the environment during synthesis 884495-22-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1083169-00-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1083169-00-9, name is 4-Bromo-2-methoxy-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of intermediate 6c (0.1M solution in THF, 66 mL,6.6 mmol) was added to a solution of 4-bromo-2-methoxy-6-methylpyridine (CAS: 1083169-00-9; 1.21 g, 6.00 mmol) and Pd(/-Bu3P)2 (140 mg, 0.27 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was treated with NH4Cl (sat., aq.) and extracted with EtOAc. The organic layer was dried (Na2S04), filtered and the solvent was evaporated in vacuo. The crude mixture was purified by flash column chromatography (S1O2, (0434) EtOAc in heptane, gradient from 100:0 to 80:20) to afford intermediate 31 (1 g, 54%).

According to the analysis of related databases, 1083169-00-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; TRESADERN, Gary John; CONDE-CEIDE, Susana; (212 pag.)WO2019/243528; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem