Pyridine-derivatives

Synthetic Route of 70165-31-0, 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 70165-31-0 as follows.

A tetrahydrofuran solution of a boranetetrahydrofuran complex (1 M; 50 mL) was added to a solution of 6-cyanonicotinic acid (0.85 g) in tetrahydrofuran (20 mL) under ice-water cooling, followed by stirring at room temperature overnight. Methanol was added to the mixture under ice-water cooling, and then a 10% hydrogen chloride in methanol was added to the mixture, followed by stirring for 1 hour at 40C at room temperature. The solvent was removed under reduced pressure, and the resultant residue was purified by means of silica gel column chromatography [Chromatorex NH] (eluent; methanol : methylene chloride=1 : 1) to prepare the titled compound (1.54 g, Example Intermediate 36-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,70165-31-0, its application will become more common.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; EP1445250; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 78686-83-6, 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 78686-83-6, name is Methyl 2-chloro-5-iodonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 5-(3-Chloro-5-methvIphenyl)-2-(l -methyl- 1H-pyrazol-4-vQ nicotinic acid (2-2)To a solution of methyl 2-chloro-5-iodonicotonate {2?_, 1.00 g, 3.36 mmol) in dimethylformamide (15 mL) at 25 C was added 3-chloro-5-methylboronic acid (0.573 g, 3.36 mmol; synthesized via procedures found in Org. Lett. 2007, P, 757-760), PdCl2dppf (0.246 g, 0.336 mmol) followed by IM aqueous cesium carbonate (13.5 mL, 13.5 mmol) and the system was stirred for 4h at 25 C. The system was partitioned between water and EtOAc, and dried over magnesium sulfate. Filtration and concentration yielded a brown solid which upon tritiration with ether afforded a tan solid. To this tan solid (0.05 g, 0.169 mmol) in dimethylformamide (0.8 mL) at 25 C was added l-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H pyrazole (0.038 g, 0.186 mmol), PdCl2dppf (0.012 g, 0.017 mmol) followed by 4M aqueous cesium carbonate (0.67 mL, 0.675 mmol) and the system was stirred for 15 minutes at 135 C in the microwave. The system was partitioned between water and EtOAc. The aqueous layer was then acidified using 25% citric acid to a pH of 3, extracted with EtOAc and the organic layer was dried over magnesium sulfate. Filtration and concentration afforded the title compound (2-2) as a cream solid. ESI+ MS [M+H]+ C17H14ClN3O2 = 328.0.

According to the analysis of related databases, 78686-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/20642; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-13-2, 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.74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.

To a solution of 5-bromopyridin-3-ol (LI) (174 mg, 1.0 mmol) in DMF (3 mL) was added potassium carbonate (415 mg, 3.0 mmol). The slurry was heated at 90C for 1 hour and then cooled to 25C. The (bromomethyl)benzene (LV) (171 mg, 1.0 mmol) was added and the mixture was stirred at 25C overnight. The reaction was worked-up using a saturated sodium bicarbonate and ethyl acetate extraction. The product was purified by ISCO column eluted with 40- 100% EtOAc-Hexanes. The 3-(benzyloxy)-5-bromopyridine (LVI) (105 mg, 0.398 mmol, 39.8 % yield) was obtained as yellow oil.. MS: 266.1. ESIMS found for C12H10BrNO m/z 266.1 (M+H).

Statistics shows that 74115-13-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-pyridinol.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (322 pag.)WO2016/40193; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5912-18-5 , The common heterocyclic compound, 5912-18-5, name is 4,6-Dichloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4Cl2N2, 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.

4,6-dichloro-1H-pyrrolo[2,3-b]pyridine (1.0 eq) was dissolved in DMF and the temperature was lowered to minus 10 C.To the mixture was added N-iodosuccinimide (1.1 equivalent), the temperature was raised to room temperature, and stirred for 1 hour. After the reaction, ice water was added to induce precipitation. The formed precipitate was filtered to give the desired compound as white. (Yield: 100%).

The synthetic route of 5912-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dae Caliber Buk Peak Medical Industry Promotion Foundation; Korea Research Institute of Bioscience and Biotechnology; Daegu Gyeongbuk Institute of Science & Technology; Choi Hwan-geun; Go Eun-hwa; Cho Jung-hui; Son Jeong-beom; Go I-gyeong; Park Jin-hui; Kim So-yeong; Kang Seok-yong; Lee Seung-yeon; Ryu Hui-yun; Kim Nam-du; Kim Sang-beom; Lee Seon-hwa; Kim Da-ye; Lee Seon-ju; Cho Seong-chan; Lee Gyu-seon; Ryu Gwon; Choi Mi-ri; Gu Ja-uk; Huh Hyang-suk; (84 pag.)KR101896568; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5470-17-7, 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 5470-17-7 as follows.

In a 250 mL round bottom flask, 3-bromo-2-chloro-5-nitropyridine (3 g, 12.63 mmol), ammonium chloride (1.35 g, 25.2 mmol) and zinc dust (8.79 g, 134 mmol) were suspended in MeOH (50 ml). The reaction mixture was heated for 2 hrs at 90 C. The reaction was cooled to room temperature, filtered over celite, and concentrated in vacuo. The resulting solid was adsorbed onto silica and purified by silica gel chromatography (25-55% EtO Ac/Heptane). The title compound (1.85 g, 8.92 mmol, 70.6 % yield) was obtained as a yellow solid. LCMS (m/z): 219.1 (MH+); retention time = 0.77 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-17-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William, R.; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; MARTIN, Eric, J.; PAN, Yue; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66070; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68325-15-5 , The common heterocyclic compound, 68325-15-5, name is 3-Chloro-4-cyanopyridine, molecular formula is C6H3ClN2, 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.

Reference Production Example 80To a mixture of 1.39 g of 3-chloro-isonicotinonitrile, 1.10 g of 2,2,2- trifluoroethanol and 5 mL of DMF, 0.40 g of 60% sodium hydride (oily) was added under ice cooling, followed by stirring for 20 minutes, heating to room temperature and further stirring for 7.5 hours. After ice cooling again, 0.20 g of 60% sodium hydride (oily) was added, followed by heating to room temperature and further stirring for 15 hours. Under ice cooling, water was added and the precipitated crystal was washed with water, collected by filtration and then dried under reduced pressure to obtain 1.63 g of 3-(2,2,2-trifluoroethoxy)- isonicotinonitrile. H-NMR (CDC13 ) delta : 8.53-8.52(br m, 1H), 8.51(d, J=4.9Hz, 1H), 7.53(dd, J=4.9, 0.6Hz,1H), 4.62(q, J=7.7Hz, 2H)

The synthetic route of 68325-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49222; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885266-91-1, 1-(2-Aminopyridin-4-yl)ethanol, 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, Recommanded Product: 885266-91-1, blongs to pyridine-derivatives compound. Recommanded Product: 885266-91-1

To a solution of 8-(tert-butylamino)-6-chloro-2-(2-hydroxyethyl)-2,7-naphthyridin- l(2H)-one (29.6 mg, 0.10 mmol) in 1,4-dioxane (1 mL) were added crude l-(2-aminopyridin-4-yl)ethanol (estimate 0.20 mmol), Cs2CO3 (130.3 mg, 0.40 mmol), and a catalytic amount of Pd(dba)3 and Xantphos. The reaction mixture was purged with N2 and heated at 100 C overnight. The mixture was then cooled, quenched with H2O and extracted with EtOAc. The combined organic layer was concentrated and purified by preparatory LC/MS to provide title compound; 1H NMR (CD3OD, 400 MHz) delta 8.16 (d, /= 5.6 Hz, 1H), 7.69 (s, 1H), 7.23 (d, / = 7.6 Hz, 1H), 6.97 (d, /= 5.6 Hz, 1H), 6.59 (s, 1H), 6.24 (d, / = 7.6 Hz, 1H), 4.81 (q, / = 6.4 Hz, 1H), 3.99 (t, /= 5.2 Hz, 2H), 3.81 (t, /= 5.2 Hz, 2H), 1.57 (s, 9H), 1.45 (d, / = 6.4 Hz, 3H); ESI-MS ml z 398.2 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885266-91-1, 1-(2-Aminopyridin-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; CHE, Jianwei; CHEN, Bei; DING, Qiang; HAO, Xueshi; HE, Xiaohui; JIANG, Songchun; JIN, Qihui; JIN, Yunho; LIU, Hong; LIU, Yahua; OKRAM, Barun; UNO, Tetsuo; WU, Xu; YANG, Kunyong; ZHU, Xuefeng; WO2011/14515; (2011); A1;,
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

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: 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