Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 885588-12-5, 2-Bromo-5-fluoro-4-pyridinecarboxylic acid, 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, 885588-12-5, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Bromo-5-fluoro-4-pyridinecarboxylic acid

To a cooled solution of 2-bromo-5-fluoroisonicotinic acid (3.0 g, 13.6 mmol) in benzene (20 ml) and methanol (10 ml) is dropwise over a period of 15 min added under stirring and cooling (trimethylsiliyl)diazomethane (2 M in ether, 14 ml, 28 mmol). The yellow solution is stirred for 1.5 h without cooling and evaporated to dryness. Purification of the residue (3.3 g) bychromatography on a 50 g Silicycle silica cartridge using a heptane / ethyl acetate 10-50% gradient affords methyl 2-bromo-5-fluoroisonicotinate (2.82 g, 88.4%) as a light yellow solid, mp.: 43 – 6C. MS: m/z= 233.9 (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,885588-12-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GOBBI, Luca; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; PETERS, Jens-Uwe; WO2012/76430; (2012); 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. 1065267-14-2, name is (3,5-Difluoropyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. name: (3,5-Difluoropyridin-2-yl)methanol

[Step 2] Production of 4-chloro-2-[(3,5-difluoropyridin-2-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridine To 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (200 mg) and (3,5-difluoropyridin-2-yl)methanol(185 mg) was added THF (8 mL) and then added NaH (60% dispersion in oil, 59 mg) under ice water cooling, then the mixture was stirred at room temperature for 3 hours. After that phosphorus trichloride (175 mg) was added to the mixture under ice water cooling, and the mixture was stirred for 30 minutes. The reaction mixture was added with aqueous sodium bicarbonate solution, water and ethyl acetate, and subjected to extraction. The organic layer was dried over anhydrous sodium sulfate, filtered off, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (63 mg) as a white powder.

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, 1065267-14-2, (3,5-Difluoropyridin-2-yl)methanol.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; TSUJI, Takashi; SHIRAI, Masaaki; EP2891656; (2015); 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. 5315-25-3, name is 2-Bromo-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Bromo-6-methylpyridine

Preparative Example 65 (0977) (0978) Step A (0979) To a stirred solution of n-butyllithium (1 L, 1.6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at -10 C. under an N2 atmosphere for 30 minutes. The ice bath was removed and the reaction mixture was cooled to -78 C. A solution of 2-bromo-6-methyl pyridine (100 g, 0.58 mol) in THF (1.6 L) was added and the color changed pale yellow to dark brown. The mixture was stirred for 1 hour at the same temperature and then N,N?-dimethylformamide (200 mL, 2.147 mol) was added. After 60 minutes at -78 C., methanol (1.6 L) and acetic acid (160 mL, 2.49 mol) were added. Then sodium borohydride (28 g, 0.557 mol) was added at -78 C. and the mixture was allowed to come to room temperature and was stirred overnight. The color changed dark brown to yellow color. The reaction mixture was diluted with ethyl acetate (3.0 L) and 10% citric acid solution (1.5 L) and was extracted with EtOAc (2×2 L), and washed with brine (1 L). The combined organic extracts were dried over Na2SO4 and solvents were removed under reduced pressure. The residue was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate/n-heptane (30/70) to afford the title compound as a pale yellow oil (90 g, 76.5%). (0980) 1H-NMR (400 MHz, CDCl3): delta=7.43 (t, 1H), 7.34 (d, 1H), 7.16 (d, 1H), 4.02 (q, 2H), 3.09 (t, 1H), 3.01 (t, 2H)

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, 5315-25-3, 2-Bromo-6-methylpyridine.

Reference:
Patent; AC IMMUNE SA; PIRAMAL IMAGING SA; KROTH, Heiko; NAMPALLY, Sreenivasachary; MOLETTE, Jerome; GABELLIERI, Emanuele; BENDERITTER, Pascal Andre Rene; FROESTL, Wolfgang; SCHIEFERSTEIN, Hanno; MUELLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; (228 pag.)US2017/2005; (2017); A1;,
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. 142266-62-4, name is 2,5,6-Trichloronicotinamide. A new synthetic method of this compound is introduced below., Quality Control of 2,5,6-Trichloronicotinamide

To a mixture of 2,5,6-trichloronicotinamide (Intermediate P; 1.4 g, 6.1 mmol) in THF (12 mL) was added oxalyl chloride, 2 M solution in DCM (3.3 mL, 6.5 mmol) at rt and the mixture was stirred and heated at 65 C. for 3 h. The mixture was cooled to 0 C. To the cooled mixture was added a solution of 1,4-diisopropyl-1H-pyrazol-5-amine (Intermediate 161; 1.03 g, 6.13 mmol) in THF (5 mL) and the mixture was stirred at rt for 15 h. The reaction mixture was quenched with satd NaHCO3 (100 mL), extracted with EtOAc (2*50 mL), washed with brine (1*50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (eluent: 0-50% EtOAc-EtOH (3:1)/heptane) to provide 2,5,6-trichloro-N-((1,4-diisopropyl-1H-pyrazol-5-yl)carbamoyl)nicotinamide (2.43 g, 5.79 mmol, 94% yield) as orange syrup. 1H NMR (400 MHz, DMSO-d6) delta 11.36 (br s, 1H), 9.39 (br s, 1H), 8.63 (s, 1H), 7.33 (s, 1H), 4.37 (dt, J=13.3, 6.6 Hz, 1H), 2.64-2.75 (m, 1H), 1.33 (d, J=6.4 Hz, 6H), 1.13 (d, J=7.0 Hz, 6H), m/z (ESI, +ve ion): 417.6 (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, 142266-62-4, 2,5,6-Trichloronicotinamide.

Reference:
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); 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. 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde, the common compound, a new synthetic route is introduced below. Formula: C6H4FNO

A suspension of 6-fluoronicotinaldehyde 31 (1.809 g, 14.46 mmol), methyl 4-hydroxybenzoate 32 (2 g, 13.15 mmol), and K2CO3 (1.998 g, 14.46 mmol) in DMF (26.3 ml) was stirred at 110 C. for 4 h. LCMS indicated the reaction was complete. Upon cooling, the reaction was quenched with water. The resulting solid was collected by filtration and rinsed with water and dried in vacuo to yield compound 33 (3.30 g, 12.84 mmol, 95.1% yield). LCMS ESI: calculated for C14H11NO4=258.1 (M+H+), found 258.0 (M+H+). 1H NMR (400 MHz, CHLOROFORM-d) delta 10.01 (s, 1H), 8.63 (d, J=2.4 Hz, 1H), 8.23 (dd, J=8.6, 2.4 Hz, 1H), 8.17-7.97 (m, 2H), 7.27-7.22 (m, 2H), 7.10 (d, J=8.6 Hz, 1H), 3.93 (s, 3H).

The synthetic route of 677728-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; POUDEL, Yam B.; GANGWAR, Sanjeev; HE, Liqi; SIVAPRAKASAM, Prasanna; BROEKEMA, Matthias; COX, Matthew; TARBY, Christine M.; ZHANG, Qian; (75 pag.)US2020/38403; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1004294-58-9, 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 1004294-58-9, name is 6-Bromo-5-chloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Di-tert-butyl dicarbonate (19 g, 87 mmol) was added to a stirring mixture of 6-bromo-5-chloro-2-pyridinamine (8.6 g, 42 mmol, from Step 1), dichloromethane (83 mL), and N,N-diisopropylethylamine (22 mL, 120 mmol) at room temperature under a nitrogen atmosphere. After 14 h, 4- (dimethylamino)pyridine (0.51 g, 4.2 mmol) was added. After an additional 3 h, the reaction mixture was concentrated under a vacuum, and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was isolated, and was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate), filtered, and concentrated under a vacuum. The residue was dissolved with dichloromethane, silica gel (40 g) was added to the solution, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (9: 1 hexane- ethyl acetate). The isolated material was dissolved with dichloromethane, silica gel (20 g) was added to the solution, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (19: 1 hexane-ethyl acetate) to give di-tert-butyl (6-bromo-5-chloro-2- pyridinyl)imidodicarbonate (6.3 g) as a colorless solid.

According to the analysis of related databases, 1004294-58-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1702-17-6, 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 1702-17-6, name is 3,6-Dichloropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

(Step 1) Synthesis of: 3,6-dichloro-N-(1-methyl-1H-pyrazol-3-yl)pyridine-2-carboxamide; To a pyridine (500 ml) solution of 30 g of 3,6-dichloro-2-pyridinecarboxylic acid were successively added 16.7 g of 1-methyl-1H-pyrazol-3-amine and 38.9 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and the mixture was stirred at room temperature for 3 hours. Pyridine was distilled off under reduced pressure, and 700 ml of water was added to the obtained residue, and the mixture was stirred for 1 hour to crystallize, thereby giving 36.7 g of the title compound as a pale yellow solid.

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 1702-17-6, 3,6-Dichloropicolinic acid.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2236507; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17228-64-7, 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. 17228-64-7, name is 2-Chloro-6-methoxypyridine, molecular formula is C6H6ClNO, 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 the solution of Compound 57 (10.0 g, 69.6 mmol, 1.00 eq) in THF (200 mL) andNMP (20.0 mL) was added Fe(acac)3 (1.23 g, 3.48 mmol, 0.05 eq). Then i-PrMgC1 (2 M, 41.79 mL, 1.20 eq) was added dropwise at -30 C within 30 mm. The mixture was stirred at 0 C for 1 h. The reaction mixture was quenched with saturated aqueous NH4C1 (80 mL) at 0 C. Then the two phases were separated and the aqueous phase was extracted with methyl t-butyl ether (80 mL). The combined organic phases were washed with water (4 x 50 mL). Then the organic phase was dried over anhydrous Na2504, filtered and concentrated to give compound 58 (7.10 g, 46.9 mmol, 67% yield) as a yellow liquid which was used for the next step without purification.?H NMR (400MHz, Chloroform-d) oe = 7.48 (t, J 7.7 Hz, 1H), 6.72 (d, J 7.1 Hz, 1H), 6.54 (d, J 7.9 Hz, 1H), 3.93 (s, 3H), 2.95 (td, J 6.8, 13.7 Hz, 1H), 1.28 (d, J= 7.1 Hz, 6H).

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 17228-64-7, 2-Chloro-6-methoxypyridine.

Reference:
Patent; AFFERENT PHARMACEUTICALS INC.; HAWLEY, Ronald Charles; IBRAHIM, Prabha; FORD, Anthony, P.; GEVER, Joel, R.; (171 pag.)WO2017/160569; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 171178-45-3, 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. 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate, molecular formula is C10H13ClN2O2, 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.

(c) 5-(tert-Butoxycarbonyl)-2-chloroisonicotinic acid. To a solution of tert-butyl 6-chloropyridin-3-ylcarbamate (1O g, 0.045 mol) and N, N, N’, N’-tetramethyleethylenediamine (20 mL) in dry Et2O (200 mL) was added n- BuLi (2.5 M solution in hexanes, 84 mL) dropwise with stirring at -78C. After the addition, the reaction mixture was warmed to -15C and stirred at the same temperature for 2 hours. The mixture was cooled to -78C and CO2 gas was bubbled into the reaction solution at -78C for 1 hour. The reaction mixture was then stirred at room temperature overnight, cooled to 0C and quenched with water. The pH of the aqueous phase was adjusted to pH=3 with IN hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over anhydrous MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the residue was dried in vacuo to give the title compound.

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 171178-45-3, tert-Butyl (6-chloropyridin-3-yl)carbamate.

Reference:
Patent; AMGEN INC.; WO2008/76425; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 881-86-7, 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 881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of pyridine-2,5-dicarboxylic acid dimethyl ester (3.55 g, 18.2 mmol.) in MeOH (100 mL) was added ammonium hydroxide (30percent, 100 mL). The reaction was stirred at room temperature for 15 min., concentrated to dryness, and purified by column chromatography (70percent ethyl acetate/hexane) to yield the product amide (1.57 g, 8.74 mmol., 48percent). 1H NMR (DMSO-d6): delta 9.10 (s, 1H), 8.48 (d, J=8 Hz, 1H), 8.27 (s, 1H), 8.18 (d, J=8 Hz, 1H), 7.83 (s, 1H), 3.92 (s, 3H). Calculated mass=180.2, [M+H]+=181. HPLC (method D) rt=4.2mins. (85.1percent).

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 881-86-7, Dimethyl pyridine-2,5-dicarboxylate.

Reference:
Patent; Wyeth; US2006/19965; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem