Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 5470-18-8, 2-Chloro-3-nitropyridine, 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, 5470-18-8, blongs to pyridine-derivatives compound. Safety of 2-Chloro-3-nitropyridine

17. Preparation of 2-Hydrazino-3-nitropyridine 2-Chloro-3-nitropyridine (100 g, 0.63 mol), hydrazine monohydrate (70.4 mL, 72.6 g, 1.45 mol) and methanol (1.3 L) were mixed and heated to reflux with stirring. After 30 min the reaction mixture was cooled and filtered collecting the insoluble materials. The filtrate was concentrated by evaporation under reduced pressure and the residue obtained as well as the insoluble materials from the filtration were diluted with water. The insoluble solids present were collected by filtration, washed with water, and dried to obtain 95.2 g (98 percent of theory) of the title compound as a bright yellow powder melting at 168-169 C. Elemental Analysis C5 H6 N4 O2 Calc.: %C, 39.0; %H, 3.90; %N, 36.4; %S, 8.27 Found: %C, 39.1; %H, 4.17; %N, 36.1; %S, 8.18

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-18-8, its application will become more common.

Reference:
Patent; DowElanco; US5571775; (1996); A;,
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. 120800-05-7, name is 1-(5,6-Dichloropyridin-3-yl)ethanone, the common compound, a new synthetic route is introduced below. Safety of 1-(5,6-Dichloropyridin-3-yl)ethanone

To a 50-mL round-bottomed flask was added l-(5,6-dichloro-3- pyridinyl)ethanone (700 mg, 3.68 mmol), cesium fluoride (28 mg, 0.18 mmol, Sigma- Aldrich, St. Louis, MO), and DME (8 mL). The reaction mixture was cooled to 0 C and under a nitrogen atmosphere (trifluoromethyl)trimethylsilane (0.65 mL, 4.42 mmol, Sigma-Aldrich, St. Louis, MO) was added. The reaction mixture was stirred at 0 C for 1.5 h and then carefully quenched by adding aqueous 5N HC1 (5 mL). The reaction mixture was stirred at room temperature for 18h. The reaction mixture was carefully diluted with saturated aqueous sodium bicarbonate (about 10 mL) and extracted with EtOAc (2 x 30 mL). The organic extract was washed with brine, dried (Na2S04), filtered, and concentrated in vacuum. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a silica gel column (40 g), eluting with a gradient of 0 % to 10% EtOAc in hexanes, to provide 2-(5,6-dichloro-3-pyridinyl)- 1,1,1 – trifluoro-2-propanol (812 mg) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.60 (d, J= 2.15 Hz, 1H), 8.27 (d, J = 2.15 Hz, 1H), 7.12 (s, 1H), 1.75 (s, 3H). (m/z (ESI, +ve ion) 260.0 (M)+.

The synthetic route of 120800-05-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-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, Safety of 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, blongs to pyridine-derivatives compound. Safety of 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

To a solution of sulfurisocyanatidic chloride (25 mg, 0.18 mmol) in DCM (2 mL) was added a solution of Intermediate GW-14.3 (60 mg, 0.18 mmol) and TEA (0.040 mL, 0.27 mmol) in DCM (2 mL) in an ice-water bath and the reaction mixture was stirred for 20 min. Then a solution of 2,3-dihydro-lH-pyrrolo[2,3-b]pyridine (32 mg, 0.27 mmol) in DCM (2 mL) was added, followed by TEA (0.07 mL, 0.5 mmol) and the reaction mixture was stirred for 2 min, the bath was removed and the stirring was continued at rt for 2 h. The reaction mixture was was concentrated and the residue was redissolved in methanol and purified by preparative HPLC to afford the title compound (13.7 mg). LC-MS retention time = 3.53 min; m/z = 565.10 [M+H]+. (Column: Phenomenex-Luna 2.0 X 50 mm, 3 muiotaeta particles; Mobile Phase A: 10% MeOH-90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1261269-66-2, 2,4,6-Trichloronicotinaldehyde, 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, 1261269-66-2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H2Cl3NO

Ethylhydrazine (2.16 g, 14.39 mmol, 1.00 equiv) was added to a solution of2,4,6-trichloropyridine-3-carbaldehyde (3 g, 14.26 mmol, 1.00 equiv) and triethylamine (4.3 g,42.49 mmol, 3.00 equiv) in ethanol (100 mL) at -78C under nitrogen. The resulting solution was stilTed for 3 hours at 0 C. After completion the reaction was concentrated under vacuum and the residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:20) to give the title compound (800 mg, 26%) as a white solid. LC-MS (ES, m/z): 216 [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,1261269-66-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6602-32-0, 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. 6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, 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.

EXAMPLE 3; MeI, K2CO3 NaOMe DMF DMF M 3-2 3.3 3-5 2:62-bromo-3 -hvdroxv-6-iodopvridine (3 -2)To a solution of 2-bromo-3 -hydroxy pyridine (3A., 28 g, 161 mmol) in water (360 mL) was added K2CO3 (44.5 g, 322 mmol) and I2 (40.8 g, 161 mmol). The system was stirred for 1.5h at ambient temperature, cooled to 00C and then treated with concentrated HCl until solids precipitated from solution (pH~ 6.0). The solids were isolated by filtration and dried to give the title compound Q1Z) as a brown solid. ESI+ MS C5H3BrINO: 299.8 found, 299.9 required.

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 6602-32-0, 2-Bromo-3-hydroxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BERGMAN, Jeffrey, M.; COLEMAN, Paul, J.; MATTERN, Mamio Christa; MERCER, Swati, P.; REGER, Thomas, S.; ROECKER, Anthony, J.; WO2010/51236; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74115-13-2, Adding some certain compound to certain chemical reactions, such as: 74115-13-2, name is 5-Bromo-3-pyridinol,molecular formula is C5H4BrNO, 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.

To a solution of NaOH (2.40 g, 1 15 mmol) in water (96mL) was added 5- bromopyridin-3-ol (10. Og, 57.5 mmol), followed by NaOCI aq. solution (60 ml of 10% solution). The reaction mixture was stirred at rt for 16 hours and then quenched with acetic acid (7 ml). The precipitate was isolated by filtration and washed with water (200 mL). After drying under high vacuum, 7.0 g of product was obtained (59%). 1H NMR (400 MHz, DMSO d6): 1 1 .36 (s, 1 H), 8.01 (d, J = 2.1 Hz, 1 H), 7.50 (d, J = 2.2 Hz, 1 H).

According to the analysis of related databases, 74115-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FU, Jiping; JIN, Xianming; LEE, Patrick; LU, Peichao; YOUNG, Joseph Michael; (76 pag.)WO2018/47109; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 777899-57-7 ,Some common heterocyclic compound, 777899-57-7, molecular formula is C7H5ClN2O4, 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.

Intermediate 27A: Methyl 2-(1 ,4-diazabicvclo[3.2.2lnonan-4-yl)-5-nitroisonicotinateTo a solution of methyl 2-chloro-5-nitroisonicotinate (Intermediate 26A) (0.1 g, 0.46 mmol) in methanol (3 mL) under nitrogen was added 1 ,4-diazabicyclo[3.2.2]nonane (0.18 g, 0.55 mmol) and triethylamine (7 mg, 0.69 mmol), reaction then stirred overnight. The reaction mixture was concentrated and purified by a 10g silica column eluting with 40% ethylacetate in hexane to afford methyl 2-(1 ,4-diazabicyclo[3.2.2]nonan-4-yl)-5- nitroisonicotinate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,777899-57-7, its application will become more common.

Reference:
Patent; N.V. ORGANON; RATCLIFFE, Paul David; CLARKSON, Thomas Russell; JEREMIAH, Fiona; MACLEAN, John Kinnaird Ferguson; WO2011/45258; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1060812-84-1, 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 1060812-84-1, name is 5-Bromopyrazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromopyrazolo[1,5-alpyridine (0.15 g, 761.30 pmol), 1-[4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyllcyclopropanecarbonitrile (245.88 mg, 913.56 jimol), Pd(t-Bu3P)2 (58.36 mg, 114.19 pmol) and K3P04 (323.20 mg, 1.52 mmol) in dioxane (2 mL) and H20 (0.2 mL) was stirred at 80 C for 16 hours. The crude product was cooled to r.t., dilutedwith H20 (10 mL), extracted with EtOAc (30 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2504, filtered and concentrated to give the crude product. The crude product was purified by silica gel column (PE: EtOAc = 10:1 to 5:1 to 1:1) to give 1 -(4- pyrazolo[1,5-alpyridin-5-ylphenyl)cyclopropanecarbonitrile (150 mg, 76% yield) as a solid. ?H NMR (400 MHz, CDC13) 011 8.53 (d, 1H), 7.99 (d, 1H), 7.72 (d, 1H), 7.64 (d, 2H), 7.41 (d, 2H),7.00 (dd, 1H), 6.58 (d, 1H), 1.83 – 1.78 (m, 2H), 1.50 – 1.46 (m, 2H).

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 1060812-84-1, 5-Bromopyrazolo[1,5-a]pyridine.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16179-97-8 , The common heterocyclic compound, 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

intermediate 9: step amethyl 5-bromo-2-(2-(pyridin-2-yl)acetamido)benzoateInto a 250-mL round-bottom flask was placed a solution of methyl 2-amino-5-bromobenzoate (5 g, 21.73 mmol), 2-(pyridin-2-yl)acetic acid hydrochloride (4.5 g, 25.92 mmol), HATU (10 g, 26.30 mmol) and D1EA (8.5 g, 65.77 mmol) in /V,N-dimethylformamide (100 mL). The resulting solution was stirred overnight at 20 C. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3×100 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/mefhanol (1 :50) to afford the title compound as a red solid.

The synthetic route of 16179-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARBAY, Kent; EDWARDS, James, P.; KREUTTER, Kevin, D.; KUMMER, David, A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald, L.; WOODS, Craig, R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell, D.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13228-40-5, 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. 13228-40-5, name is 2-(2-Pyridyl)indole, molecular formula is C13H10N2, 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.

2 – (piperidin – 2 – yl) – 1 H – indoleAt room temperature, the compound 6 c (0.5 g, 2 . 57 mmol) dissolved in acetic acid (10 ml), then two platinum oxide (0.116 g, 0 . 514 mmol) is added to the reaction, vacuum, hydrogen replacement for three times, the hydrogen in the lower, 50 C stirring reaction for 4 hours. The reaction liquid filtering, turns on lathe does, then with saturated sodium bicarbonate solution to regulate pH ? 8, aqueous phase methylene chloride (30 ml × 3) extraction, the combined organic phase with saturated salt water (50 ml) washing, anhydrous sodium sulfate drying, filtering, turns on lathe does to obtain a yellow solid compound 6 d (0.35 g, yield: 68%).

According to the analysis of related databases, 13228-40-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Fan Jiang; Wei Yonggang; Liu Zhenhong; Qin Linlin; (65 pag.)CN106928126; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem