Day: April 21, 2022

Application of 89364-04-5 , The common heterocyclic compound, 89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, 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.

After the phenoxazine 20.0g (109.16mmol), 3-Bromo-4-nitro-pyridine 25.21 g (120.08mmol), the NaO (t-Bu) 15.73 g (163.75 mmol), the Pd 2 (dba) 3 2.99 g (3.27 mmmol) was suspended in the toluene 436 mL P (t-Bu) 31.58 mL (6.55 mmol) was put and it mixed reflux underthe nitrogen air current for 24 hours. It extracts in thedichloromethane and distilled water and the organic layer the silica gel is filtered. Hexane the organic solution is removed: it recrystallized as the dichloromethane andethyl acetate and it obtained the intermediate product(I) 23.33 g (yield : 70 %) by the dichloromethane = 7 :3 (v/v) after the silica gel column.

The synthetic route of 89364-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheil Industries Co., Ltd.; Jang, Yuna; Hong, Jin Suk; Kang, Dong Min; Sin, Ji Hun; Yu, Dong Gyu; Yu, Uhn Sun; Lee, Byung Kwan; Lee, Sang Sin; Lee, Han Ir; Jung, Su Young; Han, Su Jin; (34 pag.)KR2015/41508; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 121643-44-5, 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 121643-44-5 as follows.

Preparation Example 36 2-Methoxy-3-(trifluoromethyl)pyridine (8 g), 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (17 g), and trifluoroacetic acid (32 mL) were mixed, followed by stirring at room temperature for 22 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added diisopropyl ether. The precipitated solid was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine (9.4 g) as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; KOIKE, Takanori; NEGORO, Kenji; TANAKA, Hiroaki; MAEDA, Jun; YOKOYAMA, Kazuhiro; TAKAMATSU, Hajime; (146 pag.)EP3153511; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84487-03-6, 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. 84487-03-6, name is 6-Chloro-5-nitropyridin-2-amine, molecular formula is C5H4ClN3O2, 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 mixture of 6-chloro-5-nitropyridin-2-amine(0.26 g, 1.50 mmol), benzylmercaptan (0.19mL, 1.65 mmol), K2CO3 (0.25 g, 1.83 mmol) and DMF (2.1 mL) was stirred at 80 C for 3.5 h. The mixture was poured into water and extracted with CH2CI2 (3×15 mL). The combined organic layers were dried over anhydrous Na2S04 and concentrated. The residue was dissolved in CH2CI2, and the product was precipitated by addition of hexane to give the sub-title compound (0.32 g, 83 %).

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 84487-03-6, 6-Chloro-5-nitropyridin-2-amine.

Reference:
Patent; OBLIQUE THERAPEUTICS AB; PELCMAN, Benjamin; SUNA, Edgars; STAFFORD, William; PRIEDE, Martins; (90 pag.)WO2018/146472; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19230-55-8 ,Some common heterocyclic compound, 19230-55-8, molecular formula is C6H6ClN, 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.

EXAMPLE 81 COMPOUND 81: N1-(3-chloro-5-methyl-pyridin-2-ylmethyl)-N1-(3-isopropyl-pyridin-2-ylmethyl)-butane-1,4-diamine (HBr salt) At -78 C., under N2, BuLi (2.5 M in hexanes, 0.80 mL, 2.0 mmol) was added to a solution of TMEDA (0.30 mL, 2.0 mmol) in dry Et2O (20 mL). After addition the mixture was warmed to room temperature. After stirred at room temperature for 30 min the mixture was cooled to -78 C., and added to a solution of 3-chloro-5-methyl-pyridine (0.255 g, 2.00 mmol) (Bushby et al. J. Chem. Soc. Perkin Trans. 11978, 1578) in dry Et2O (10 mL) pre-cooled at -78 C. The mixture was stirred at -78 C. for 30 min and then warmed to room temperature for 1 h. Water (15 mL) was added, and the mixture was extracted with Et2O (3*40 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (CH2Cl2) to afford 3-chloro-5-methyl-pyridine-2-carbaldehyde (0.096 g, 31%). 1H NMR (CDCl3) delta 2.44 (s, 3H), 7.65 (s, 1H), 8.54 (s, 1H), 10.28 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19230-55-8, its application will become more common.

Reference:
Patent; Bridger, Gary; McEachern, Ernest J.; Skerlj, Renato; Schols, Dominique; US2004/209921; (2004); A1;,
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.953780-40-0, name is Methyl 5-fluoro-6-methoxynicotinate, molecular formula is C8H8FNO3, molecular weight is 185.15, as common compound, the synthetic route is as follows.SDS of cas: 953780-40-0

A mixture of methyl 5-fluoro-6-methoxynicotinate (3.5 g, 18.9 mmol) and KOH (4.2 g, 61.5 mmol) in MeOH (70 ml) was stirred at room temperature for 5 h. After concentration, the residue was dissolved in water, and the obtained solution was washed with ether. The aqueous phase was acidified to pH = 1 with dilute hydrochloric acid, and extracted with ether, and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum to afford S-fluoro–methoxynicotinic acid (3.2g, 98%) as a white solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,953780-40-0, Methyl 5-fluoro-6-methoxynicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2007/120729; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89282-03-1 , The common heterocyclic compound, 89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, 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.

General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

The synthetic route of 89282-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Hee Jung; Kim, Ji-Eun; Yum, Eul Kgun; Kim, Young Hoon; Han, And Chang-Woo; Bulletin of the Korean Chemical Society; vol. 36; 1; (2015); p. 211 – 218;,
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. 35590-37-5, name is 5-Bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3BrN2

To a degassed solution of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)aniline (1.0 equiv.), 5-bromonicotinonitrile (1.1 equiv.) and Na2CO3 (5 equiv., 2M aq. sln) was added PdCl2(dppf).CH2Cl2 adduct (0.15 equiv.). This mixture was heated to 120 C for 15 min in the microwave and cooled to room temperature. Water was added, the phases were separated and the water mixture was extracted with ethyl acetate. The organic phases were pooled, dried with MgSO4 and the volatiles removed in vacuo to give 5-(5-amino-2- methylphenyl)nicotinonitrile in 99% yield. LCMS (m/z) (M+H) = 210.0, Rt = 0.43 min.

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, 35590-37-5, 5-Bromonicotinonitrile.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 211308-81-5, 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.211308-81-5, name is 2-Amino-5-chloro-3-iodopyridine, molecular formula is C5H4ClIN2, molecular weight is 254.46, as common compound, the synthetic route is as follows.

Pyruvic acid (0. 43ML, 6. 24MMOL) was added to a solution of 5-chloro-3- iodopyridin-2-ylamine (Preparation 56, 500MG, 2.08mmol), palladium acetate (23mg, 0. 10MMOL) and DABCO (700mg, 6. 24MMOL) in anhydrous DMF (20ml). The reaction mixture was degassed with argon for 20min, then heated to 110C for 16h. The solvent was removed in vacuo and the residue suspended in water (lOml) and acetic acid (5ML) and then filtered. The solid was dissolved in EtOAc (50ML), extracted into 2N NAOH solution (50ML) and the organic layer discarded. The aqueous solution was acidified with concentrated HC1 and extracted into EtOAc (2 x 40ML). The combined organics were dried (MgS04) and concentrated in vacuo to give the title compound as a beige solid. aH (CD30D): 7.14 (1H, s), 8.14 (1H, d), 8.35 (1H, d).

Statistics shows that 211308-81-5 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-chloro-3-iodopyridine.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 821791-58-6, Adding some certain compound to certain chemical reactions, such as: 821791-58-6, name is Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate,molecular formula is C9H10ClNO3, 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 821791-58-6.

(step 3) To ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (6.0 g, 28 mmol) obtained in step 2 were added N-chlorosuccinimide (4.1 g, 31 mmol) and DMF (130 mL), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water (200 mL), and the mixture was extracted with ethyl acetate. The organic layer was washed with hydrochloric acid, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0-70/30) to give ethyl 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (5.5 g, 79%). ESIMS m/z: 250 (M + H)+

According to the analysis of related databases, 821791-58-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; NAKAMURA, Rina; ARATAKE, Seiji; UCHIDA, Kenji; UENO, Kimihisa; MOTOSAWA, Maasa; KABEYA, Takahiro; EP2930170; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5006-66-6, 6-Oxo-1,6-dihydropyridine-3-carboxylic 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, COA of Formula: C6H5NO3, blongs to pyridine-derivatives compound. COA of Formula: C6H5NO3

step A) methyl 5-bromo-6-methoxynicotinate Bromine (0.60 mL) was added to a solution of 6-hydroxynicotinic acid (1.02 g) in acetic acid (5 mL) and the mixture was stirred at 60C for 16 hr. The solvent was evaporated under reduced pressure and the residue was dissolved in phosphorus oxychloride (5 mL). Phosphorus pentachloride (3.05 g) was added and the mixture was stirred at 100C for 2 hr. The solvent was evaporated under reduced pressure, and the residue was dissolved in methanol (5 mL), and the mixture was refluxed for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in methanol (10 mL). A methanol solution (28%, 2.2 mL) of sodium methoxide was added and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.18 g) as white crystals. 1H NMR (400 MHz, CDCl3) delta3.92 (3H, s), 4.08 (3H, s), 8.40 (1H, d, J = 1.8 Hz), 8.75 (1H, d, J = 1.6 Hz).

The synthetic route of 5006-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; EP2816032; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem