Pyridine-derivatives

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.82671-02-1, name is 2,6-Dichloro-5-fluoronicotinonitrile, molecular formula is C6HCl2FN2, molecular weight is 190.99, as common compound, the synthetic route is as follows.Recommanded Product: 2,6-Dichloro-5-fluoronicotinonitrile

Weigh 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (24.8 g, 130 mmol)Concentrated sulfuric acid (125 mL) was added to a 500 ml flask, and the mixture was heated to 62 C for 1 hour.After cooling to room temperature, the reaction solution was poured into ice water (800 mL) and ethyl acetate (300 mL×4).The organic phase was washed successively with water (100 mL), saturated sodium bicarbonate (100 mL) and brine (50 mL).Dry over anhydrous sodium sulfate.Filtered, the filtrate was dried,A pale yellow solid (27.0 g, 99.5%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,82671-02-1, 2,6-Dichloro-5-fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ·geerdeman; (79 pag.)CN108690016; (2018); A;,
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.147149-98-2, name is 4-Amino-2-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.Formula: C6H5F3N2

1,3-cyclopentanedione (3.3 g, 33.9 mmol) and 4-amino-2-trifluoromethylpyridine (5.0 g, 30.8 mmol) are suspended in acetic acid (15 mL) and shaken at 130 C under microwave irradiation overnight. The reaction mixture is diluted with water and purified by reversed phase HPLC. Yield: 4.17 g; ESI mass spectrum [M+H]+=243; Retention time HPLC: 0.77 min (method Z018_S04).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147149-98-2, 4-Amino-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; PETERS, Stefan; ANDERSKEWITZ, Ralf; GNAMM, Christian; HOESCH, Holger; MORSCHHAEUSER, Gerd; OOST, Thorsten; RIES, Uwe Joerg; (84 pag.)US2016/31830; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 941294-57-1, name is 5-Bromo-2-iodo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5BrIN

Step B: 5-Bromo-4-methyl-pyridine-2-carbaldehyde In an oven-dried flask the compound obtained in Step A (4.67 g) was dissolved in tetrahydrofuran (22 ml). The solution was cooled to -15 C., then isopropyl magnesium bromide (17.2 ml, 15% solution in THF) was added dropwise at a rate to keep the internal temperature between -15 C. to -10 C. The reaction was stirred at this temperature for 1 hour, then anhydrous dimethylformamide (1.8 ml) was added at a rate to keep the internal temperature below 0 C. The reaction was stirred at this temperature for 1 hour, then poured into water and extracted with diethyl ether. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude title aldehyde product (2.4 g, brown solid) was used as such in the next step.

With the rapid development of chemical substances, we look forward to future research findings about 941294-57-1.

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2012/238517; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1186647-69-7, 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A solution of 4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (103) (50 mg, 0.179 mmol) in DMF (1 mL) was cooled to 0 C, NaH (8.6 mg, 1.2 eq, 0.215 mmol) was added slowly and then 2-bromopropane was added dropwise. The solution was stirred overnight at room temperature. The mixture was concentrated in vacuo. The crude product was then purified by column chromatography using a gradient of CH2Cl2 in hexanes to afford 4-chloro-3-iodo-1-isopropyl-1H-pyrazolo[4,3-c]pyridine (301) (30 mg, 53% yield) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1186647-69-7, 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Intellikine, LLC; LIU, Yi; REN, Pingda; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; (58 pag.)EP2252293; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 151509-03-4, name is Imidazo[1,5-a]pyridine-8-carbaldehyde, molecular formula is C8H6N2O, 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. Quality Control of Imidazo[1,5-a]pyridine-8-carbaldehyde

To a solution of imidazo[1,5-a]pyridine-8-carbaldehyde (60 mg, 0.41 mmol) in H20 (10 mL) was added 1-cyclohexylethan-1-one (52 mg, 0.41 mmol) and NaHCO3 (18 mg, 0.21 mmol),the reaction was warmed to reflux and stirred at for about 40 hours. Extracted with CH2C12 (3*10 mL), the combined organic phases were washed with sat. NaC1 (5 mL), dried overanhydrous Na2504, filtered, concentrated, the crude product was purified by Pre-TLC (DCM:MeOH = 15:1), got the product (10 mg, 9.6%) as a pale yellow solid. MS (ESI) m/e [M+1] 255.1.

With the rapid development of chemical substances, we look forward to future research findings about 151509-03-4.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; ZHANG, Guoliang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHOU, Changyou; (219 pag.)WO2016/161960; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 189449-41-0, (4-Chloropyridin-3-yl)methanol, 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 189449-41-0, blongs to pyridine-derivatives compound. Product Details of 189449-41-0

Example 21 3-chloromethyl-4-chloropyridine hydrochloride Thionyl chloride (0.714 mL, 9.78 mmol) was added at room temperature to dry DMF (7 mL). After 30 min the above solution was cannulated into the solution of 3-hydroxymethyl-4-chloropyridine (700 mg, 4.89 mmol) in DMF (3 mL). After 45 min, the product was precipitated by addition of dry ether (100 ml), washed with ether, and dried in vacuum to yield 813 mg (84percent) of the title compound. 1H NMR (CD3 OD) delta5.00 (s, 2H), 8.31 (d, 1H, J=5), 8.99 (d, 1H, J=5), 9.18 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189449-41-0, (4-Chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Microcide Pharmaceuticals, Inc.; US6025352; (2000); A;; ; Patent; Microcide Pharmaceuticals, Inc.; US6057312; (2000); A;; ; Patent; Microcide Pharmaceuticals, Inc.; US6030965; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89167-19-1, 3-Bromo-4-iodopyridine, 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, name: 3-Bromo-4-iodopyridine, blongs to pyridine-derivatives compound. name: 3-Bromo-4-iodopyridine

A mixture of 1-(oxan-2-yl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.94 g, 10.57 mmol), 3-bromo-4-iodopyridine (2.00 g, 7.05 mmol), potassium carbonate (2.92 g, 21.12 mmol) and Pd(dppf)Cl2.CH2Cl2 (580 mg, 0.710 mmol) in N,N-dimethylformamide (20 mL)/water (4 mL) was heated at 80 C. for 6 h under nitrogen. The resulting solution was extracted with ethyl acetate, and the combined extracts were dried over Na2SO4, filtered, and concentrated under vacuum. Purification by silica gel chromatography (7:3 ethyl acetate/petroleum ether) provided 3-bromo-4-[1-(oxan-2-yl)-1H-pyrazol-4-yl]pyridine (2.75 g) as a yellow oil. LCMS (ESI): [M+H]+=308.2.

The synthetic route of 89167-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6295-87-0 ,Some common heterocyclic compound, 6295-87-0, molecular formula is C5H7IN2, 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.

General procedure: A clean, washed boiling tube equipped with a magnetic stir bar was charged with 1-aminopyridinium iodide (1a) (0.0665 g, 0.3 mmol),(E)-chalcone (2a) (0.0520 g, 0.25 mmol) and NMP (1 mL). The mixture was stirred for 24 h at r.t. under O2 (balloon). After completion of the reaction, the mixture was poured into hypo solution (10 mL). The mixture was extracted with EtOAc (3 × 10 mL), dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. The residue was purified through column chromatography using silica gel (20%EtOAc/hexane) to afford 3a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6295-87-0, its application will become more common.

Reference:
Article; Ravi, Chitrakar; Samanta, Supravat; Mohan, Darapaneni Chandra; Reddy, N. Naresh Kumar; Adimurthy, Subbarayappa; Synthesis; vol. 49; 11; (2017); p. 2513 – 2522;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6443-85-2, Adding some certain compound to certain chemical reactions, such as: 6443-85-2, name is 2-(Pyridin-3-yl)acetonitrile,molecular formula is C7H6N2, 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 6443-85-2.

EXAMPLE 8 (Z)-3-(9-Ethyl-9H-carbazol-3-yl)-2-(pyridin-3-yl) acrylonitrile 9-Ethyl-9H-carbazol-3-yl-carboxaldehyde (4.46 g; 0.02 mol) and 3-pyridylacetonitrile (2.36 g; 0.02 mol) were dissolved in ethanol (25 mL). Sodium methoxide (1 mL of 25% methanol solution) was added. The mixture was then left standing at ambient temperature for 24 hours. The formed precipitate was collected by filtration and dried to give 2.4 g (37% yield) of the title compound as a yellow solid, m.p. 131-133 C. Anal. Calcd. for C22 H17 N3: C, 81.71; H, 5.30; N, 12.99. Found: C, 81.38; H. 5.49; N, 12.84. Mass spectrum (EI; M+) m/z 323. 1 H-NMR (DMSO-d6; 400 MHz) delta 8.98 (d, 1H), 8.75 (d, 1H), 8.60 (dd, 1H), 8.28 (s, 1H)1, 8.18 (dd, 1H), 8.12-8.16 (m, 2H), 7.8 (d, 1H), 7.68 (d, 1H), 7.51-7.56 (m, 2H), 7.29 (t, 1H), 4.49 (q, 2H), and 1.34 ppm (t, 3H).

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. 6443-85-2, 2-(Pyridin-3-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Home Products Corporation; US5710164; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 84249-14-9, name is 2-Amino-4-bromopyridine. A new synthetic method of this compound is introduced below., Product Details of 84249-14-9

Step 1 Preparation of 7-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester To a stirred solution of 4-Bromo-pyridin-2-ylamine (4 g, 23.12 mmol) in toluene (40 mL) is added 3-Bromo-2-oxo-propionic acid ethyl ester (4.5 g, 23.12 mmol). The reaction mixture is heated at 115 C. for 16 hours. Reaction mixture is cooled to 0 C. then diluted with water and extract with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo to afford the title compound (6.5 g). 1H-NMR (400 MHz, DMSO-d6) delta: 1.31 (t, J=7.2 Hz, 3H), 4.26-4.33 (q, J=7.2 Hz, 2H), 7.18-7.20 (dd, J1=1.92 Hz, J2=7.16 Hz, 1H), 7.98 (s, 1H), 8.53 (d, J=7.32 Hz, 1H), 8.57 (s, 1H). LC-MS (m/z): [M+H]=271.0.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 84249-14-9, 2-Amino-4-bromopyridine.

Reference:
Patent; Curtis, Michael; Duclos, Brian A.; Ewin, Richard A.; Johnson, Paul D.; Johnson, Timothy Allen; Vairagoundar, Rajendran; Billen, Denis; Goodwin, Richard M.; Haber-Stuk, Andrea K.; Kyne, Graham M.; Sheehan, Susan M. K.; US2013/237502; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem