Category: pyridine-derivatives

Related Products of 62135-58-4, 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. 62135-58-4, name is Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

Under argon atmosphere, ethyl [l,2,4]triazolo[l,5-a]pyridine-2-carboxylate (1 g, 5.23 mmol) was combined with THF (10 mL) at RT to give a brown suspension. Sodium borohydride (1.19 g, 31.4 mmol) was added in four portions. The mixture was heated to 65 C for 15 min. After cooling down to RT, ethanol (10 mL) was added dropwise over a period of 15 min. The mixture was stirred at 65 C for 4 h. The mixture was cooled down to 0-5 C and NH4C1 (saturated aqueous solution, 20 mL) was added dropwise over a period of 10 min (foam.). Water (20 mL) was added and the yellow suspension was poured into dichloromethane (100 mL) and extracted with dichloromethane (4 x 75 mL). The combined organic layer was dried over MgS04 and concentrated in vacuo to give the product as light yellow solid (720 mg, 4.76 mmol, 91 %) which was used without further purification for the next step.MS: M = 150.1 (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,62135-58-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BACHMANN, Stephan; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RUDOLPH, Markus; WO2013/34506; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrN3

Potassium bis(trimethylsilyl)amide (25 mL, 12.5 mmol, 0.5M in toluene) was added to a solution of 2-amino-5-bromo-nicotinonitrile (496 mg, 2.5 mmol) in THF (10 mL) at -78 0C which was followed by a dropwise addition of acetyl chloride (533 muL, 7.5 mmol). The reaction was stirred at ambient temperature for 4 h then quenched with ammonium chloride (10 mL, sat). The resulting mixture was extracted with methylene chloride; the organic layer was washed with water and dried over MgSO_j. The volatiles were removed under vacuum to give the title compound (420 mg, 70%). 1H NMR (300 MHz, DMSO-4 delta): 10.92 (s, IH), 8.82 (d, J = 2.3Hz, IH), 8.66 (d, J= 2.3Hz, IH), 2.12 (s, 3H). MS (ESI) m/e: 240 and 242 (M+H)+.

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, 709652-82-4, 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/67416; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 185315-53-1 , The common heterocyclic compound, 185315-53-1, name is 3-Chloro-2-(chloromethyl)pyridine, molecular formula is C6H5Cl2N, 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.

Synthesis of 4.5-dichloro-2-((3-chloropyridin-2-vnmethvnpyridazin-3(2HV one (G3-2 32 G3-2 To a solution of compound 4 (200 mg, 1.21 mmol), compound 32 (235 mg, 1.45 mmol) and K2CQ3 (335 mg, 2.42 mmol) in DMF (3 mL) was added KI (20 mg, 0.12 mmol). The solution was stirred at 90 C for 2h. The mixture was cooled to room temperature and quenched with water, extracted with EtOAc for 3 times, combined the organic layer, washed with brine, dried over Na2S(X filtered, concentrated under reduced pressure, purified by HPLC to give G3-2 (126 mg, 42%) as a yellow solid. NMR (DMSO-ifc, 300 MHz): delta 5.53 (s, 2H), 7.38-7.42 (m, 1H), 7.99 (d, J = 8.1 Hz, 1H), 8.27 (s, 1H), 8.41 (d, J = 4.5 Hz, 1H); LCMS [mobile phase: 20-95% Acetonitrile +0.02% NHtOAc] purity is >95%, Rt = 3.365 min; MS Calcd.: 290; MS Found: 291 (M+l)+.

The synthetic route of 185315-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; BECKWITH, Jonathan Roger; DUTTON, Rachel; ESER, Markus; LANDETA, Cristina; BLAZYK, Jessica L.; MEEHAN, Brian M.; HATAHET, Feras; BOYD, Dana; WO2015/143164; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1079179-12-6 ,Some common heterocyclic compound, 1079179-12-6, molecular formula is C5H2ClFN2O2, 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 a solution of 2-chloro-3-fluoro-5-nitropyridine (3.0 g, 15.3 mmol) in DMF (30 mL) was added thiomorpholine (1.6 g, 15.3 mmol) and DIEA (5.3 mL, 30.6 mmol). The mixture was stirred at 60C for 16 hours. The reaction was cooled to roomtemperature, and then then was diluted with water (50 mL). The precipitated solid was collected by filtration, and dried to give 4-(3-fluoro-5-nitropyridin-2-yl)thiomorpholine asa solid. ?HNMRoe 8.87 (s, 1H), 7.98 (dd, J= 2.0, 13.6Hz, 1H), 4.15-4.12 (m, 4H), 2.76-2.74 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1079179-12-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YANG, Lihu; OLSEN, David B.; YOUNG, Katherine; SU, Jing; MANDAL, Mihir B.; SUZUKI, Takao; YOU, Lanying; (85 pag.)WO2017/66964; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, molecular formula is C7H6ClNO2, 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.

At -78 C., 19.6 ml of 1.9 mol/L solution of hexamethyldisilazane sodium in THF was added dropwise to 100 ml of THF solution containing 2.00 g of 2-(2-chloropyridin-3-yl)acetic acid, and the mixture was stirred for 10 minutes. Next, 1.50 ml of methyl p-fluorobenzoate was added dropwise. The mixture was then brought from -78 C. to room temperature and was stirred for 1 hour. Saturated aqueous ammonium chloride solution was added thereto, and the mixture was stirred. Thereafter, ethyl acetate was added, and the resultant liquid mixture was separated. The obtained organic layer was washed with saturated brine and was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography. The title compound was obtained as a colorless amorphous compound weighing 1.45 g. 1H-NMR(CDCl3)delta:8.36(1H,dd,J=4.6,1.9 Hz),8.11-8.07(2H,m),7.62(1H,dd,J=7.4,1.9 Hz),7.27-7.24(1H,m),7.21-7.17(2H,m),4.42(2H,s).

According to the analysis of related databases, 61494-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUI CHEMICALS AGRO, INC.; UMETANI, Hideki; FUKUMOTO, Takeshi; NAITO, Ryohei; IKISHIMA, Hideaki; KOUNO, Toshiyuki; NISHIDA, Akihiro; YANAGI, Masanori; KITAJIMA, Kazuki; YUTANI, Satoshi; SHIRAKAWA, Tomomi; OHARA, Toshiaki; (170 pag.)US2019/380340; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90395-45-2 ,Some common heterocyclic compound, 90395-45-2, molecular formula is C13H11NO, 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-(4-Pyridin-3-ylphenyl)-ethanone (33 g, 166.8 mmole),3,5-Dibromo-benzaldehyde (42.06 g, 159.34 mmole), and 840 ml of ethanol were added to the reaction flask for stirring.Finally, sodium tert-butoxide (22.94 g, 239 mmole) was added and stirred at room temperature.After the reaction has been completed, 200 ml of deionized water is added and stirred for filtration. The solid is filtered and washed with deionized water and methanol. The solid is then filtered with 100 ml of deionized water and 200 ml of methanol for 30 minutes, and repeated twice. Dry the solid to give 55 g of pale yellow solid 3-(3,5-dibromophenyl)-1-(4-pyridin-3-ylphenyl)-acetone(3-(3,5-Dibromo-phenyl)-1-(4-pyridin-3-yl-phenyl)-propanone),The yield was 77.89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90395-45-2, its application will become more common.

Reference:
Patent; E-ray Optoelectronics Technology Co Ltd; Huang, Heh Lung; Guo, Huang Ming; Chao, Teng Chih; Lin, Chi Jen; Chang, Min Jong; (53 pag.)TW2019/30287; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256785-86-0, 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.1256785-86-0, name is 1-(4-Aminopyridin-2-yl)ethanone, molecular formula is C7H8N2O, molecular weight is 136.15, as common compound, the synthetic route is as follows.

Example 20 (2R,5S)-N-(2-Acetyl-4-pyridyl)-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carboxamide While stirring with ice-cooling, 12.5 ml of trifluoroacetic acid was added to 12.5 ml of chloroform solution containing 1.41 g of 2-acetyl-4-pyridinylcarbamic acid t-butyl ester.. The mixture was immediately warmed up to room temperature and stirred for 2 hours and 40 minutes.. The solvent was evaporated under reduced pressure to obtain a crude amine.. This compound was dissolved in 25 ml of pyridine, and the solution was mixed with 0.83 ml of phenyl chloroformate while stirring with ice-cooling and then immediately warmed up to room temperature.. After 8 hours and 30 minutes, this was mixed with 10 ml of pyridine solution containing 1.4 g of (2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile and heated under reflux for 1 hour.. The reaction mixture cooled to room temperature was mixed with water and extracted with chloroform.. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure.. The residue was purified by a silica gel column chromatography to obtain 1.03 g of the title compound from methanol-chloroform (1:99, v/v) elude. NMR: 1.10 (3H, d, J=7), 1.20 (3H, d, J=7), 2.61 (3H, s), 3.34-3.52 (2H, m), 3.75 (1H, d, J=14), 3.92 (1H, d, J=14), 4.28-4.45 (1H, m), 4.46-4.62 (I H, m), 7.20-7.35 (2H, m), 7.78-7.91 (2H, m), 8.12 (1H, d, J=2), 8.48 (1H, d, J=6), 9.24(1H, s)

The chemical industry reduces the impact on the environment during synthesis 1256785-86-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co. Ltd.; US6673799; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1083057-12-8, 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 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate. This compound has unique chemical properties. The synthetic route is as follows.

The 3-butyl 3-(3-methylpyridin-2-yl)benzoate (1.0 eq.) was dissolved in EtOAc (6 EtOAc). Water (0.3 vol) and hydrogen peroxide urea (3 eq.) were added in that order. Phthalic anhydride (3 equivalents) was then added portionwise to the mixture in solid form at a rate to maintain the temperature in the reactor below 45 C. After the addition of phthalic anhydride was completed, the mixture was heated to 45 C. After stirring for another 4 hours, the heater was turned off. A 10% w/w aqueous Na2SO3 solution (1.5 eq.) was added via an addition funnel. After the addition of Na2SO3 was completed, the mixture was stirred for additional 30 min and the layers were separated. The organic layer was stirred and a 10% wt/wt aqueous Na2CO3 solution (2 eq.) was added. After stirring for 30 minutes, the layers were separated. The organic phase was washed with a 13% w/v NaCl aqueous solution. The organic phase was then filtered and concentrated to give crude 2-(3-(t-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) which was used directly in the next step .

According to the analysis of related databases, 1083057-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, MARINUS JACOBUS; ALARGOVA, ROSSITZA GUEORGUIEVA; KAUSHIK, RITU ROHIT; KADIYALA, IRINA NIKOLAEVNA; YOUNG, CHRISTOPHER; (118 pag.)TWI636051; (2018); B;,
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.72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

240 mg (1.19 mmol) of 2-chloro-5-(trifluoromethyl)pyridin-3-amine and 357 mg (1.31 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid were dissolved together with 0.39 ml (4.78 mmol) of pyridine in 20 ml of dioxane, 367 mg (2.39 mmol) of phosphoryl chloride were added, and the mixture was stirred at reflux for 90 min. The mixture was concentrated, the residue was taken up in ethyl acetate and washed with water, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography purification with a cyclohexane/ethyl acetate gradient (80:20 to 40:60) as eluent. (log P (neutral): 5.71; MH+: 412; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 1.37 (t, 3H), 3.12 (q, 2H), 7.74-7.84 (m, 2H), 8.07-8.14 (m, 2H), 8.49 (s, 1H), 8.70 (s, 1H), 9.02 (s, 1H), 11.12 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; HAGER, Dominik; HOFFMEISTER, Laura; KAUSCH-BUSIES, Nina; WILCKE, David; WILLOT, Matthieu; GOeRGENS, Urich; ILG, Kerstin; MOSRIN, Marc; PORTZ, Daniela; TURBERG, Andreas; US2018/305353; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0 ,Some common heterocyclic compound, 628691-93-0, molecular formula is C6H3ClFNO2, 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.

Carbonyldiimidazole (1.80 g, 1 1.1 mmol) was added to a solution of 2-chloro-3-fluoro- isonicotinic acid (1.3 g, 7.41 mmol) in THF (21.2 mL). The reaction mixture was stirred at RT overnight and was then added to a cold (0C) solution of NaBH4 (1.40 g, 37 mmol) in water (52.9 mL). The mixture was stirred for 10 min at 0C, and 1 M HCI was then added carefully to quench the reaction (caution: H2 evolving). Volatiles were removed via rotary evaporation and the residue was dissolved in saturated aqueous NaHC03. The mixture was extracted repeatedly with CH2CI2, the combined organics were dried (phase separator) and concentrated in vaccuo. Purification by flash column chromatography on silica gel (eluent gradient: c- hexane/EtOAc 4: 1 to 2: 1) afforded the title compound as a white solid. TLC, Rf (c- hexane/EtOAc 1 :1) = 0.37; MS (LC/MS): 162.0 [M+H]+; tR (HPLC conditions b): 1.60 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628691-93-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; SIMIC, Oliver; VULPETTI, Anna; ROGEL, Olivier; WO2012/93101; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem