Day: June 22, 2021

Application of 88912-26-9, Adding some certain compound to certain chemical reactions, such as: 88912-26-9, name is 2,5-Dichloroisonicotinic acid,molecular formula is C6H3Cl2NO2, 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 88912-26-9.

To a methanolic solution of 2, 5-dichloro- isonicotinic acid was added H2SO4 (cone) (0.5 mL) and the solution was heated to reflux for 12 h. The mixture was cooled to room temperature, neutralized with aqueous NaHCO3, extracted into EtOAc and evaporated to afford the methyl ester (6-2) in 89% yield.

According to the analysis of related databases, 88912-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOTA SCIENTIFIC MANAGEMENT PTY LTD; WO2008/141385; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884495-37-8, 2-Chloro-5-fluoropyridin-3-amine, 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, Recommanded Product: 2-Chloro-5-fluoropyridin-3-amine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-fluoropyridin-3-amine

A degassed solution of 2-chloro-5-fluoro-3-amino-pyridine (3.5 g), 4- (4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,6-dihydro-2/f-pyridine-l-carboxylic acid tert-butyl ester (8.89 g) (prepared as described in WO 2006/003494) and bis(triphenylphosphine)palladium(II) chloride (0.84 g) in dioxane (157 ml) was treated with a degassed solution of sodium carbonate (7.6 g) in water (72 ml). The reaction mixture was stirred at reflux for 1 hour, cooled to ambient temperature and the solvent evaporated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel (eluent: cyclohexane / ethyl acetate 8:2) afforded 3-amino-5-fluoro-3′,6′-dihydro-2’H-[2,4′]bipyridinyl-r-carboxylic acid tert-hutyl ester (4.6 g) as a solid. MS (ES+) 294 (MEta+), 238 (M-isoprene); IH NMR (400 MHz, CDCl3) 1.48 (s, 9H), 2.53 (m, 2H), 3.64 (t, 2H), 3.99 (m, 2H), 4.08 (m, 2H), 5.99 (m, IH), 6.70 (dd, IH), 7.85 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884495-37-8, 2-Chloro-5-fluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; CASSAYRE, Jerome Yves; CORSI, Camilla; MAIENFISCH, Peter; WO2010/9968; (2010); 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.58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Recommanded Product: 58584-86-4

(a) Ethyl6-{4-[(benzylsulfonyl)carbamoyl]piperidin-1-yl}-2-chloronicotinate A micro wave vial was charged with DIPEA (2.73 g, 21.1 mmol), ethyl2,6-dichloronicotinate (Example 43(a)) (1.547 g, 7.03 mmol), N-(benzylsulfonyl)piperidine-4-carboxamide (Example 6(d)) (2.28 g, 8.08 mmol) and DMF and the mixture was heated to 120 C. for 10 minutes followed by 150 C. for 10 minutes using microwave single node heating. Ratio of the two possible regioisomers was ca. 1:1 together with some bis-addition adduct. The crude product was purified by first using HPLC (Kromasil C8, 10 mum, using a gradient of MeCN with an acidic second eluent (H2O/MeCN/AcOH, 95/5/0.1)) followed by flash chromatography using a stepwise gradient of heptane/EtOAc 1/1 then heptane/EtOAc 1/1+0.15% FA and finally heptane/EtOAc 1/2+0.15% FA. (Rf product (heptane/EtOAc 1/2+0.15% FA)=0.47) to give ethyl6-{4-[(benzylsulfonyl)carbamoyl]piperidin-1-yl}-2-chloronicotinate. Yield: 610 mg (19%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-86-4, Ethyl 2,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; US2008/171732; (2008); 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. 944401-77-8, name is 2-Amino-4-fluoropyridine, the common compound, a new synthetic route is introduced below. name: 2-Amino-4-fluoropyridine

Step 1. 5-bromo-4-fluoropyridin-2-amine To a solution of 4-fluoropyridin-2-amine (400 mg, 3.57 mmol) in acetonitrile (35. 7 mL) was added NBS (648 mg, 3.64 mmol) in three portions at 0 C. The reaction mixture was stirred at 0 C. for 20 min. LCMS showed the reaction complete. After quenched with sat Na2S2O3 and NaHCO3, stirred for 30 min. The reaction mixture was extracted with EtOAc 3 times. Washed by sat NaHCO3, water and brine. Dried and concentrated. The crude material was triturated with ether and taken to the next step without further purification. LCMS (m/z): 192.9 (MH+), 0.32 min.

The synthetic route of 944401-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
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

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

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 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 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

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