Category: pyridine-derivatives

Related Products of 19842-08-1 ,Some common heterocyclic compound, 19842-08-1, molecular formula is C7H8BrN, 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.

In a 2 L round-bottomed flask was charged n-butyllithium 2.5M hexanes (99 ml, 248 mmol) in Et2O (1680 ml) to give a colorless solution. The reaction was cooled to -78 C. n-Butyllithium 2.5M hexanes (99 ml, 248 mmol) was added dropwise keeping the temperature below -70 C. The reaction was stirred for 1 hour and N,N-dimethylformamide (36.6 ml, 473 mmol) was added keeping the temperature below -70 C. The reaction was stirred for 1 hour and quenched with saturated ammonium chloride solution (2 L). The organic layer was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure. The crude residue was purified by column chromatography eluting with 0-30% ethyl acetate to give 6-bromonicotinaldehyde. Yield 19.7 g, 44.8%In a 2 L round-bottomed flask was added Methyltriphenylphosphonium bromide (42.9 g, 120 mmol) in THF (600 ml) and cooled to -20 C. n-Butyllithium 2.5M hexanes (48.0 ml, 120 mmol) was added dropwise keeping the temperature below 0 C. The reaction was warmed to room temperature for 20 minutes and cooled back to 0 C. A solution of 6-bromonicotinaldehyde (18.6 g, 100 mmol) in THF (40 mL) was added. The reaction was warmed to room temperature and stirred overnight. The reaction was partitioned between water and diethyl ether (1 L) and the organic layer was dried over sodium sulfate, filtered and solvent removed at room temperature under reduced pressure. The product, 2-bromo-5-vinylpyridine, was purified by bulb to bulb distillation (600 mTorr, 80-100 C.). Yield 17.2 g, 93%2-Bromo-5-vinylpyridine (17.2 g, 40.1 mmol) was dissolved in ethanol (150 mL) and Adam’s Catalyst (PtO2, 75%, 1.4 g) was added. The mixture was hydrogenated at 3 psi of hydrogen, continually checking the progress of the reaction by LC and 1H NMR between each charge of hydrogen. After 10 psi was consumed, the data showed completion of the reaction with <5% of reduction of the bromine. The catalyst was filtered off and the solvent was removed under reduced pressure at 20 C. to give 2-bromo-5-ethylpyridine. Yield 17 g, 98%.In a 1 L round-bottomed flask was compound 6 (10 g, 53.8 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (13.83 g, 59.1 mmol) in Dioxane (300 ml) followed by saturated sodium bicarbonate (150 ml). The mixture was degassed by passing a stream of nitrogen through the mixture for 20 minutes. Tetrakis(triphenylphosphine) palladium(0) (3.36 g, 2.91 mmol) was added and the mixture was heated to reflux becoming very thick then finally going to solution. The reaction was heated for 2 hours, cooled to room temperature and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure. The residue was purified by column chromatography 0-100% ethyl acetate/heptane to give 3-(5-ethylpyridin-2-yl)-4-methylaniline. Yield 8.7 g, 77%The urea was formed from 3-(5-ethylpyridin-2-yl)-4-methylaniline and 4-(2-amino-5-tert-butylthiophene-3-carbonyl)-3,3-dimethylpiperazine-2-one. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19842-08-1, its application will become more common. Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5 ,Some common heterocyclic compound, 73406-50-5, molecular formula is C8H9NO3, 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.

2-(Pyrrolidin-1-yl)carbonyl-3-hydroxy pyridine 18 g (0.093 moles) of ethyl-3-hydroxypicolinate [J. Heterocyclic Chem. 23 , 665, 1986] were cooled at -5C and ml 250 of pyrrolidine were added under nitrogen atmosphere. After the addition, the solution was allowed to reach room temperature, stirred 24 h and then evaporated in vacuo to give 15 g of the title compound as a slight yellow oil which crystallized on standing.

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. 73406-50-5, Ethyl 3-hydroxypicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smithkline Beecham Farmaceutici S.p.A.; EP447704; (1991); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-53-0, Adding some certain compound to certain chemical reactions, such as: 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol,molecular formula is C7H6F3NO, 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 131747-53-0.

3.78 g of carbon tetrabromide and 2.78 g of triphenylphosphine were added to a solution containing 1.70 g of the (6-trifluoromethylpyridin-2-yl) methanol obtained in (4) dissolved in 30 ml of methylene chloride followed by stirring for 1 hour at room temperature. 30 ml of acetonitrile, 1.52 g of N-(t-butoxycarbonyl) hydroxylamine and 1.74 g of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) were added to this reaction solution followed by stirring for 3 hours at room temperature. Following completion of the reaction, aqueous ammonium chloride solution was added to the reaction mixture followed by extraction with ethyl acetate. The ethyl acetate layer was dried by addition of anhydrous magnesium sulfate followed by filtration and distilling off the solvent from the filtrate under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate = 3:1 (volume ratio)) to obtain 1.54 g of the target compound of t-butyl N-[(6-trifluoromethylpyridin-2-yl)methyloxy] carbamate (yield: 59%). [1H-NMR Data of t-Butyl N-[(6-trifluoromethylpyridin-2-yl)methyloxy] Carbamate 1H-NMR (CDCl3/TMS, delta ppm): 7.90(dd,1H), 7.73(d,1H), 7.62(d,1H), 7.44(bs,1H), 1.48(s,9H)

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. 131747-53-0, (6-(Trifluoromethyl)pyridin-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Soda Co., Ltd.; EP2218711; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a stirred solution of 1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine dihydrochloride (7 g, 35.70 mmol, 1 equiv.) and 4,5-dichloro-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (10.7 g, 42.84 mmol, 1.2 equiv.) in DMA(100 mL) was added DIEA(13.8 g, 107.10 mmol, 3 equiv.) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred for overnight at 100 degrees Celsius under nitrogen atmosphere. The reaction was monitored by LCMS. The resulting mixture was extracted with EtOAc (100 x mL). The combined organic layers were washed with brine (3×100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. This resulted in 4-chloro-2-(oxan-2-yl)-5- [1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridin-5-yl]-2,3-dihydropyridazin-3-one (8.5 g, 70.91%) as a light y

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62002-31-7, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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. 20970-75-6, name is 2-Cyano-3-methylpyridine, the common compound, a new synthetic route is introduced below. Product Details of 20970-75-6

General procedure: To a 25 mL round-bottom flask equipped with magnetic stirrer were added nitrile (2 mmol), acetaldoxime (6 mmol), sodium molybdate (VI) dihydrate (0.2 mmol) and H2O (10 mL). The mixture was heated to reflux for 5-16 h. After cooling to room temperature, the solution was directly evaporated to dryness and the residue was purified by column chromatography on silica gel (ethylacetate/n-hexane) to give the corresponding amide.

The synthetic route of 20970-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Xiaoyun; He, Ying; Lu, Ming; Synthetic Communications; vol. 44; 4; (2014); p. 474 – 480;,
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 60186-15-4, name is 2,4-Difluoro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H2F2N2O2

2-Fluoro-5-nitro-4-(2,2,2-trifluoroethoxy)pyridine.A solution of 2,4-difluoro-5- nitropyridine (0.1523 g, 0.951 mmol) intetrahydrofuran (2 mL) was cooled to 0 C. 2,2,2-Trifluoroethanol (0.082mL, 1.142 mmol) was added to the mixture. After 5 min, triethylamine (0.265 mL,1.903 mmol) was added. The reaction was stirred at 0 C for 1 h, and thenallowed to warm to rt. The reaction was stirred at rt for 4.5 h. The solventwas removed in vacuo and the crude product carried on without furtherpurification.

With the rapid development of chemical substances, we look forward to future research findings about 60186-15-4.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
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. 1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine, the common compound, a new synthetic route is introduced below. Safety of 2-Chloro-3-fluoro-5-nitropyridine

Step 2 To a stirred solution of 2-chloro-3-fluoro-5-nitropyridine (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) under nitrogen atmosphere were added tributylvinyl tin (3.42 g, 10.8 mmol), Pd2(dba)3 (0.42 g, 0.45 mmol) and trifuryl phosphene (0.2 g, 0.9 mmol). The reaction mixture was deoxygenated thoroughly and was heated to 60 C. for 6 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3*25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5% ethyl acetate in n-hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine (1.5 g, 96%).

The synthetic route of 1079179-12-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 886365-47-5 ,Some common heterocyclic compound, 886365-47-5, molecular formula is C7H5BrClNO, 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.

Starting material l-(5- bromo-2-chloropyridin-3-yl)ethanone (5.8 g, 24.7 mmol) and 100 ml anhydrous hydrazine was charged into 500 ml round bottom flask and the resulting mixture was allowed to stir at room temperature for overnight. After removing the excess hydrazine via rotatory evaporation under reduced pressure, the remaining residue was diluted with distilled water and solid was appeared. After filtering the water, the resulting solid was taken up in ethylacetate and saturated aqueous sodium bicarbonate and was extracted by ethylacetate twice. The combined organic layer was washed with water and brine and dried over sodium sulfate. The crude product was eluted through a short silica gel column (3 inch in length) with ethylacetate as a white solid (4.0 g, y=77%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,886365-47-5, its application will become more common.

Reference:
Patent; AMGEN, INC.; WO2006/44860; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22353-40-8, 2,3-Dichloro-5-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, name: 2,3-Dichloro-5-nitropyridine, blongs to pyridine-derivatives compound. name: 2,3-Dichloro-5-nitropyridine

2,3-Dichloro-5-nitropyridine (3.9 g) and iron powder (3.0 g) were added to isopropyl alcohol (40 ml) and water (8 ml) and the mixture refluxed for 4 hours. The mixture was then cooled to room temperature and filtered (celite). The filtrate was evaporated under reduced pressure and chromatographed ?SiO2; hexane:ethyl acetate (80:20) to[(50:50)] to give 5-amino-2,3-dichloropyridine (1.71 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22353-40-8, 2,3-Dichloro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Zeneca Limited; US5922732; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884494-82-0, 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. 884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid, molecular formula is C7H6FNO3, 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.

In a round bottom flask, 5-fluoro-2-methoxy-nicotinic acid (150, 250 mg, 1.46 mmol) was combined with thionyl chloride (3.00 mL, 41.1 mmol) and the suspension was stirred at room temperature for 3 hours. The reaction was concentrated to dryness under vacuum to provide the desired compound, used in the next step without further purification.

According to the analysis of related databases, 884494-82-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Plexxikon Inc.; Zhang, Jiazhong; Ibrahim, Prabha N.; Bremer, Ryan; Spevak, Wayne; Cho, Hanna; US9096593; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem