Day: March 25, 2022

Reference of 1256834-13-5 , The common heterocyclic compound, 1256834-13-5, name is 4-Bromo-6-chloronicotinic acid, molecular formula is C6H3BrClNO2, 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 6-bromo-4-chloronicotinic acid (3 g, 12.69 mmol) in DMF (42 mL) was added HATU (6.27 g, 16.49 mmol), (R)-4-amino-3-fluoro-2-methylbutan-2-ol hydrochloride (2.4 g, 15.23 mmol), and N,N-Diisopropylethylamine (5.62 ml, 32.26 mmol). The resulting solution was stirred at room temperature overnight and subsequently diluted with ethyl acetate. The organic solution was washed with saturated aqueous lithium chloride (3 times), then dried over Na^SCri. and then concentrated. The residue was purified by silica gel chromatography (eluent: EtO Ac/hexanes) to provide (R)-6-bromo-4-chloro-N-(2-fluoro-3-hydroxy-3- methylbutyl)nicotinamide.ES/MS: 341.1 (M+H+).

The synthetic route of 1256834-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; AMMANN, Stephen; BACON, Elizabeth M.; BRIZGYS, Gediminas; CHIN, Elbert; CHOU, Chienhung; COTTELL, Jeromy J.; NDUKWE, Marilyn; TAYLOR, James G.; WRIGHT, Nathan E.; YANG, Zheng-Yu; ZIPFEL, Sheila M.; (138 pag.)WO2020/36979; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4966-90-9 ,Some common heterocyclic compound, 4966-90-9, molecular formula is C6H6N2O4, 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)2,4-dichloro-6-methyl-3-nitropyridine 6-methyl-3-nitropyridin-2,4-diol (1.7 g, 10 mmol) was dissolved in 10 mL POCl3, heated to 95C, and stirred for 1.5 h. The excess POCl3 was removed through centrifugation. 100 mL ice water was carefully added. The reaction solution was extracted with ethyl acetate (80 mL*3). The organic phase was combined, washed with saturated brine, dried with anhydrous Na2SO4 and spinned to dryness to afford 1.773 g yellow powder with a yield of 85.7 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4966-90-9, its application will become more common.

Reference:
Patent; Xuanzhu Pharmaco., Ltd.; EP2524917; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77199-09-8, 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 77199-09-8, name is Ethyl 5-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Example 593-(((5-(l-(4-(2,3-Dimethylphenoxy)butanoyl)-l,2,3,4-tetrahydroquinolin-5-yl)pyridin-2- yl)methoxy)carbonylamino)propanoic acid[00204] To a solution of NaBH4 (0.822 g, 21.73 mmol) in MeOH (25 mL) was added ethyl 5-bromopicolinate (1.0 g, 4.35 mmol) portion-wise over a period of 10 min at room temperature. The mixture was stirred at room temperature for 10 min and then heated to 70 C for 30 min. The solvent was removed in vacuo, and the resulting residue was diluted with EtOAc and water. The aqueous phase was adjusted to pH 7 with 1 N aq. HCl, and extracted with EtOAc. The combined organic layer was dried over MgS04, filtered, and concentrated in vacuo to afford the title compound (0.65 g, 80% yield) as a white solid. LCMS, [M+H]+ = 187.9.

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 77199-09-8, Ethyl 5-bromopicolinate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ROBL, Jeffrey A.; LI, Jun; KENNEDY, Lawrence J.; WALKER, Steven J.; WANG, Haixia; WASHBURN, William N.; AHMAD, Saleem; NGU, Khehyong; WO2012/149236; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72716-80-4, 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 72716-80-4, name is 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 3-cyano-5,6-dimethyl-2-pyridone (1-013-02) (12.0 g) in water (293 mL) was added conc. hydrochloric acid (293 mL), and the reaction mixture was reflux with stirring in oil-bath at 135 C. After 3 days, the reaction mixture was cooled, and evaporated under reduced pressure. To the residue (24.75 g) were added chloroform (300 mL) and methanol (15 mL), and the reaction mixture was heated in a water bath at 65 C, and the dissolble material was filtered off. Furthermore, the dissolble material was treated by chloroform (200 mL) and methanol (10 mL) in a similar manner to described above. The combined filtrates were evaporated under reduced pressure. To the obtained residue (13.26 g) were added methanol (150 mL) and potassium carbonate (10 g). After stirred at room temperature for 30 min, the dissolble material was filtered off. The filtrate was evaporated under reduced pressure. To the obtained residue (14.7 g) was added chloroform (200 mL), and the dissolble material was filtered off again. The filtrate was evaporated under reduced pressure to give 5,6-dimethyl-2-pyridone (1-013-03) (9.41 g, 94.3%, m.p.: 202-207 C)1H NMR (300 MHz, CDCl3): delta 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J = 9.0 Hz, 1H), 7.26 (d,J = 9.0 Hz, 1H), 13.17 (br s, 1H).

According to the analysis of related databases, 72716-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1477186; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-96-8, 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 22282-96-8, name is 2-Bromo-6-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 6-bromo-2-methyl-3-nitropyridine (XIV) (250 g, 1.15 mol, 1.00 eq) and NH4C1 (300 g, 5.61 mol, 4.88 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 65C. To this mixture was added Fe (130 g, 2.33 mol, 2.02 eq) and HC1 (15.3 g, 419 mmol, 0.36 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 L x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-2-methylpyridin-3-amine (XV) as brown solid (373 g, 1.99 mol, 86.7% yield) which was used for the next step without any purification. ?H NMR (DM50-cl6, 400 MHz) ppm 6.01 (dd, J= 2.3, 7.9 Hz, 2H), 7.03 (d, J= 8.2 Hz, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).

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 22282-96-8, 2-Bromo-6-methyl-5-nitropyridine.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23993; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866775-18-0, 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 866775-18-0 as follows.

Step 1: 3-Amino-6-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)picolinic acid3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) (500 mg, 1.672 mmol), PdCl2(dppf).CH2Cl2 adduct (205 mg, 0.251 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (383 mg, 1.839 mmol) and Cs2CO3 (6.69 ml, 6.69 mmol) in THF (12 ml) under N2, was heated using microwave radiation at 150 C. for 10 minutes. 2M NaOH (5 ml) was added and the mixture was stirred at RT overnight. The mixture was filtered through Celite (filter material) and the organic solvent was removed. The resulting aqueous layer was washed with EtOAc and acidified to pH1. The product was extracted with DCM and concentrated in vacuo to afford the title compound;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,866775-18-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; US2011/230483; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 777931-67-6, 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 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.

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 777931-67-6, 3-Bromo-2-chloro-6-methoxypyridine.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
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. 947249-27-6, name is 2-Bromo-3-(difluoromethoxy)pyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-3-(difluoromethoxy)pyridine

To a steel bomb were charged with 2-methoxyethanol (20ml), 2-bromo-3-(difluoromethoxy)pyridine (1.95g, 8.7 mmol), cone. aqueous NH4OH (28-30%, 5 ml, 79 mmol) and Cu2O (0.25 g,, 1.7 mmol). The reaction mixture was heated at 100 0C for 23 h, then cooled to 0 0C, and partitioned between mixture of EtOAc/aq. 3 N NaOHZH2O (40ml/10ml/30ml). The organic phase layer was collected, washed with saturated aqueous NaHCO3 solution (30ml), brine (40ml), dried (Na2SO^, and concentrated to produce 1.12 g of 3-(difiuoromethoxy)pyridin-2-amine which was carried forward without further purification: LCMS (m/z, MH+): 161.0, tR = 0.31min.

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, 947249-27-6, 2-Bromo-3-(difluoromethoxy)pyridine.

Reference:
Patent; NOVARTIS AG; WO2009/115572; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 185041-05-8 ,Some common heterocyclic compound, 185041-05-8, molecular formula is C7H5ClINO2, 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.

Containing 4 g of 2-chloro-4-iodo-nicotinate (12.87 mmol) in 50 ml dimethylformamide solution, was added 3.6 g of t-butyl cyanoacetate (25.75 mmol, 2 eq.), 7.1 g potassium carbonate (51.5 mmol, 4 equiv.) and 13 mg of cuprous iodide (0.1 mmol, 0.01 eq.) and the solution was stirred overnight at 50 deg.] C, the solvent is removed to give residue was purified with silica gel column to give the product, 4- (2-tert-butoxy-1-cyano-2-oxoethyl) -2-chloro-nicotinic acid methyl ester (2.8 g, 66% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,185041-05-8, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; ARNDT, JOSEPH; CHAN, TIMOTHY; GUCKIAN, KEVIN; KUMARAVEL, GNANASAMBANDAM; LEE, WEN-CHERNG; LIN, EDWARD YIN-SHIANG; SCOTT, DANIEL; SUN, LIHONG; THOMAS, JERMAINE; VAN VLOTEN, KURT; WANG, DEPING; ZHANG, LEI; ERLANSON, DANIEL; (469 pag.)TWI525093; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19235-89-3, 4-Chloropyridine-2-carbonitrile, 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: 4-Chloropyridine-2-carbonitrile, blongs to pyridine-derivatives compound. name: 4-Chloropyridine-2-carbonitrile

Potassium carbonate (9.00 g) was dried in vacuo with heating, cooled to RT under nitrogen. 4-amino-3-ntrophenol (3.355 g), 4-chloro-2-cyanopyridine (3.00 g) and DMSO (30 mL, anhydrous) were added. The system was stirred under nitrogen as it was heated to 103 C., and held at this temperature 1 hr. The reaction was then cooled to RT, poured onto ice/H2O (500 mL) the precipitate was collected, washed (H2O), dissolved (EtOAc), dried (Na2SO4), filtered and stripped to a solid. This was suspended (Et2O), collected, air-dried 4.1015 g (73.5%) a second crop was collected (0.5467 gm, 10%). M/z=257 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19235-89-3, 4-Chloropyridine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Amiri, Payman; Fantl, Wendy; Levine, Barry Haskell; Poon, Daniel J.; Ramurthy, Savithri; Renhowe, Paul A.; Subramanian, Sharadha; Sung, Leonard; US2004/122237; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem