Category: pyridine-derivatives

Electric Literature of 153034-94-7 , The common heterocyclic compound, 153034-94-7, name is 2-Fluoro-4-iodo-5-picoline, molecular formula is C6H5FIN, 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.

Step 1: ethyl 4-(2-chlorophenyl)-1-(2-fluoro-5-methylpyridin-4-yl)-1H-pyrrole-3-carboxylate To a slurry of copper(I) iodide (0.14 g, 0.73 mmol) and potassium carbonate (3.03 g, 21.9 mmol) in 1,4-dioxane (15 mL) were added 2-fluoro-4-iodo-5-methylpyridine (5.03 g, 21.2 mmol), ethyl 4-(2-chlorophenyl)-1H-pyrrole-3-carboxylate (0.95 g, 3.8 mmol), and trans-N,N’-dimethylcyclohexane-1,2-diamine (0.23 mL, 1.46 mmol). The reaction mixture was allowed to stir in a sealed vial for 48 h at 105 C. and then allowed to cool to rt. The mixture was diluted with EtOAc and washed with brine. The organic solutions were combined, concentrated, and purified by column chromatography to give ethyl 4-(2-chlorophenyl)-1-(2-fluoro-5-methylpyridin-4-yl)-1H-pyrrole-3-carboxylate (1.2 g, 88%). LCMS (FA): m/z=359.3 (M+H).

The synthetic route of 153034-94-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 115170-40-6, 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 115170-40-6 as follows.

To a solution of 5-bromo-2,3-dihydro-1 H-pyrrolo(2,3-b)pyridine (CAS Number 1 15170-40-6; 0.300 g, 1 .507 mmol) in 1 ,4-dioxane:water (1 : 1 , 8 ml) were added phenylboronic acid (0.294 g, 2.412 mmol) and K2CO3 (0.624 g, 4.52 mmol) at rt. The reaction mixture was degassed for 30min before addition of Pd(PPh3)4 (0.087 g, 0.075 mmol) thenheated at 80C for 1 h. The reaction was cooled to rt, poured into water (100 ml) and extracted with EtOAc (3 x 50 ml). The combined organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure yielding 5-phenyl-2,3-dihydro-1 H-pyrrolo[2,3-b]pyridine (0.440 g, 2.24 mmol). MS: ES+ 197.1 .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115170-40-6, its application will become more common.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (167 pag.)WO2018/65768; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 114-33-0, 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. 114-33-0, name is N-Methylnicotinamide, molecular formula is C7H8N2O, 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.

Appropriate nitrogen donor ligand (1 mmol) was added to an aqueous solution of copper(II) acetate (0.5 mmol) under stirring. After a few minutes, x-methylsalicylic acid (1 mmol) and the necessary amount of solvent (ethanol or acetonitrile) were added to reach the final volume (30-40 mL). Eventually, the reaction mixture was stirred for few days at room temperature until the reaction finished. The precipitate was filtered off and the mother liquids were left to crystallize at room temperature and the crystals were dried at room temperature. The obtained crystals were suitable for X-ray structure determination.

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 114-33-0, N-Methylnicotinamide.

Reference:
Article; Pucho?ova, Miroslava; ?vorec, Jozef; ?vorc, Lubomir; Valigura, Du?an; Chemical Papers; vol. 70; 1; (2016); p. 75 – 81;,
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. 87109-10-2, name is 3-Phenylpyridin-2-amine. A new synthetic method of this compound is introduced below., name: 3-Phenylpyridin-2-amine

To a solution of 3-phenylpyridin-2-amine (10.0 g, 55.8 mmol) and di-tert-butyl dicarbonate (48.7 g, 223 mmol) in DCM (200 mL) was added DMAP (13.6 g, 112 mmol) in batches. The resulting mixture was stined at 26 C for 16 h, then washed with brine (100 mL x 3), dried over Na2SO4and concentrated. The residue was purified by flash silica gel chromatography (ISCO; 120 g SepaFlash Silica Flash Column, EtOAc in petroleum ether: 0- 40%, 50 mL/min, dry loaded) to give the title compound.?H NMR (400 MHz, CDC13) oe 8.52 (d, J = 3.1 Hz, 1H), 7.75 (dd, J = 1.6, 7.4 Hz, 1H), 7.34-7.45 (m, 6H), 1.30 (s, 18H).

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, 87109-10-2, 3-Phenylpyridin-2-amine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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.

(1)A solution of methylpiperazine (2.31 g) in tetrahydrofuran (20 mL) was cooled to -78° C., and n-butyllithium (2.64 M, 7.55 mL) was added dropwise in an argon gas atmosphere.After stirring at the same temperature for 15 minutes, a solution of 6-methoxypicolinaldehyde (2.5 g) in tetrahydrofuran was added and the mixture was stirred for 30 minutes. t-Butyllithium (1.59 M, 17.1 mL) was added dropwise to the reaction solution, and the mixture was stirred at the same temperature for one hour and at -40° C. for 15 minutes.The reaction solution was cooled again to -78° C. A solution of hexachloroethane (12.9 g) in tetrahydrofuran (20 mL) was slowly added dropwise, and the mixture was stirred at the same temperature for 30 minutes.The reaction solution was poured into water, followed by extraction with ethyl acetate.The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1?10:1) to give 5-chloro-6-methoxypyridine-2-carbaldehyde as a colorless powder (1.21 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-96-4, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52568-28-2, 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.52568-28-2, name is 2-(Pyridin-2-yl)propan-2-amine, molecular formula is C8H12N2, molecular weight is 136.19, as common compound, the synthetic route is as follows.

General procedure: To a solution of the acid (1 equiv.) in DCM (0.2 M) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.), DIPEA (1.2 equiv.) at 0 C. After the mixture was stirred for 10 min, the amine (1.2 equiv.) was added. The reaction was stirred overnight at room temperature. Then water was added and the mixture was extracted with DCM. The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography on silica gel to give the desired product.

The chemical industry reduces the impact on the environment during synthesis 52568-28-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Haifeng; Niu, Youhong; Zhang, Guoying; Ye, Xin-Shan; Tetrahedron Letters; vol. 57; 41; (2016); p. 4544 – 4548;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 271-63-6, 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 271-63-6, name is 1H-Pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

a) 7-aza indole 100g (0.846mol), 12g Ni / Al2O3 (10% w.t), toluene 200g was added to the autoclave and stirred to obtain a reaction solution A;b) The autoclave was replaced with nitrogen 8 times, and hydrogen was replaced 4 times. Reaction liquid A was reacted at 2Mpa of hydrogen at a temperature of 130C.c) filtering the hydrogenation mixture obtained in step b), filtering out the catalyst to obtain a filtrate B;d) After recovering the organic solvent from the filtrate B, 94.59 g of the 7-azaporphyrin product was obtained, the yield was 93.4%, and the gas chromatographic purity of the product was ?98%.

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 271-63-6, 1H-Pyrrolo[2,3-b]pyridine.

Reference:
Patent; Zhonggang Group Anshan Heat Energy Institute Co., Ltd.; Wang Haiyang; Wang Shoukai; Xu Zhe; Zhao Wei; Jiang Hui; Jin Dan; Xu Haoran; (7 pag.)CN107987076; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 27048-04-0 ,Some common heterocyclic compound, 27048-04-0, molecular formula is C5H4ClN3O2, 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.

Stage A: 2-amino-6-methoxy-3-nitropyridine 1.65 g (0.0717 mol; 2 equivalents (eq)) of sodium are dissolved in 100 cm3 of methanol. 6.2 g (35.7 mmol) of 2-amino-6-chloro-3-nitropyridine are added and the solution is brought to reflux for 8h. The methanol is evaporated under reduced pressure and the residue is taken up in the minimum amount of water (20 cm3). The solution is extracted with 100 cm3 of ethyl ether. The ether phase is washed with water (20 cm3), separated by settling, dried over MgSO4, decolored with animal charcoal and evaporated on a rotary evaporator to give a 1 st crop. The aqueous phase is extracted under the same conditions with 2 times 50 cm3 of ethyl acetate, giving a 2nd and 3rd crop. 4.7 g (0.0278 mol; yield: 77.7%) of a yellow powder are obtained. Melting point: 172 C.

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. 27048-04-0, 6-Chloro-3-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Adir Et Compagnie; US5599812; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1150617-54-1, 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. 1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine, molecular formula is C6H4BrN3, 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.

A solution of n-butyllithium in hexane (2.2 molar equivalent) was added at low temperature to a solution of 6-bromo-1H-pyrazolo[4,3-b]pyridine (0.5 g) in dry THF (20 mL) cooled with a dry ice actone bath. After stirring the mixture at low temperature for 90 minutes, iodine was added (703 mg, 1.1 molar equivalent) and the mixture stirred for another hour before let rise to around 5 C. and quenched with a saturated solution of ammonium chloride. The mixture was extracted with EA and washed with water. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a residue that was purified by chromatography (SiO2, heptane/EA) to afford 6-iodo-1H-pyrazolo[4,3-b]pyridine. MS (ES): M/Z [M+H]=246. The synthesis of 6-bromo-1H-pyrazolo[4,3-b]pyridine is described in Example 182 part f.

According to the analysis of related databases, 1150617-54-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Soll, Mark David; Hir de Fallois, Loic Patrick Le; Huber, Scot Kevin; Lee, Hyoung Ik; Wilkinson, Douglas Edward; Jacobs, Robert Toms; Beck, Brent Christopher; US2010/125089; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59782-85-3, 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. 59782-85-3, name is 2,5-Dichloronicotinic acid, molecular formula is C6H3Cl2NO2, 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.

To a solution of 2,5-dichloronicotinic acid (30 g, 0.16 mol) in toluene (100 ml) was added ethanol (50 ml) and conc. sulfuric acid (1 ml). The reaction mixture was heated at 130 C for 3 days with stirring. Then the reaction mixture was cooled and poured into sat. sodium bicarbonate solution. The whole mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried (sodium sulfate), and concentrated to afford 34 g (quant. ) of title compound: ‘H-NMR (CDCI3) 8 8.48 (1 H, d, J = 2.6 Hz), 8.15 (1 H, d, J = 2.6 Hz), 4.44 (2H, dd, J = 7.1, 14.3 Hz), 1.42 (3H, t, J = 7.1 Hz).

According to the analysis of related databases, 59782-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/102389; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem