Day: March 23, 2022

Reference of 401892-47-5, 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 401892-47-5, name is 5-Bromo-2-chloro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-bromo-2-chloro-4-iodopyridine (20.0 g, 63.09 mmol) in DMF (200 mL), methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (16.15 mL, 126.18 mmol) and Cul (24.02 g, 126.18 mmol) were added at RT under argon atmosphere. The reaction mixture was heated to 100 C for 6 hours. The reaction mixture was diluted with water (200 mL) filtered off and washed with w-pentane (2 X 500 mL) and cold water (3 X 1000 mL). The separated organic layer dried over with sodium sulfate and concentrated under reduced pressure at 30 C to give the crude compound. That was purified by column chromatography (5% pet ether: EtO Ac) that resulted in the title compound (9.0g, 44%) as a liquid compound. TLC: 5% EtO Ac in pet ether. LCMS [M+H]+ = 261.0 g/mol.

According to the analysis of related databases, 401892-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; (316 pag.)WO2017/147701; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 3430-18-0, 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. 3430-18-0, name is 2,5-Dibromo-3-methylpyridine. A new synthetic method of this compound is introduced below.

Under an argon atmosphere, a solution of 2 M isopropylmagnesium chloride in THF (5.5 ml) was cooled to -78 C., and a solution of 2,5-dibromo-3-methylpyridine (2.5 g) in THF (10 ml) was added dropwise. After stirring at the same temperature for 30 minutes, a solution of morpholine-4-carboaldehyde (1.26 g) in THF (5 ml) was added dropwise thereto, followed by elevating the temperature to 0 C. over 30 minutes, followed by stirring at 0 C. for 2 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 6-bromo-5-methyl nicotine aldehyde (1.42 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3430-18-0, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; US2012/184520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15862-50-7, 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 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Morpholine (54 mul), cesium carbonate (336 mg), Pd2(dba)3 (57 mg), and Xantphos (72 mg) were added to a 1,4-dioxane (3 ml) solution containing 3-bromo-2-methoxy-5-nitropyridine (96 mg) in a nitrogen atmosphere, followed by stirring at 100C for 10 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane : ethyl acetate = 4:1 to 2:1), and a yellow solid of 2-methoxy-3-morpholino-5-nitropyridine (54 mg) was thus obtained. MS (ESI m/z): 240 (M+H) RT (min): 1.21

According to the analysis of related databases, 15862-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; FUJIWARA, Hideyasu; SATO, Kimihiko; MIZUMOTO, Shinsuke; SATO, Yuichiro; KURIHARA, Hideki; KUBO, Yohei; NAKATA, Hiyoku; BABA, Yasutaka; TAMURA, Takashi; KUNIYOSHI, Hidenobu; HAGIWARA, Shinji; YAMAMOTO, Mari; (630 pag.)EP2589592; (2018); B1;,
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.2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, molecular weight is 111.1169, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Diisopropylamine (910.7 mg, 1.261 mL, 9.000 mmol) was dissolved in dry TetaF(20mL) and cooled to -78 0C, n-Buli (3.600 mL of 2.5 M, 9.000 mmol) was added slowly dropwise and the resultant mixture was then allowed to warm to -20 0C over 40min before being cooled back down to -78 0C.[ 00363 ] A solution of 2-fluoro-5-methyl-pyridine (1.0 g, 9.000 mmol) in dry THF(1OmL) was added dropwise and the solution was stirred at this temp for 2 hours. A solution of iodine (2.284 g, 463.3 muL, 9.000 mmol) in THF (1OmL) was then added and the resultant mixture stirred for a further 1 hour at this temp before being quenched with water. The resulting mixture was partitioned between sodium thiosulfate solution and Et2theta, organics separated and washed further with saturated NaCl. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a colourless oil. The resulting mixture was purified by column chromatography (30% EtOAc in hexanes, ~200mL silica) to give a colourless foam (1.409g, 66% Yield). 1 H NMR (400.0 MHz, DMSO) d 1 .42 (s, 1 H) and 7.07 – 7.12 (s, 2H) ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2369-19-9, 2-Fluoro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/73300; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 96630-88-5, 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.96630-88-5, name is 4-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.5444, as common compound, the synthetic route is as follows.

a) A solution of diazenedicarboxylic acid diethyl ester (0.1572 mol) in THF (163 ml) was added dropwise to a mixture of 4-chloro-3-pyridinol (0.1429 mol), 2-propen-1-ol (0.1572 mol) and triphenyl-phosphine (0.1572 mol) in THF (276 ml), that was cooled with an ice-water bath and under nitrogen flow.The formed mixture was stirred on the ice-water bath for 15 minutes and at room temperature overnight.The mixture was concentrated under vacuum and the residue was washed with a saturated Na2CO3- solution.The mixture was extracted with DCM and the separated organic layer was dried, filtered and the solvent was evaporated until dry.The residue was treated with DIPE and the formed solid was filtered off and discarded.The filtrate was evaporated until dry and the residue was treated with diethyl ether and the formed solid was filtered off and discarded again.The filtrate was evaporated until dry and the residue was purified by open column chromatography over silica gel (eluent: DCM/2-propanone 99/1;98/2).The product fractions were collected and the solvent was evaporated, yielding 7.9 g of 4-chloro-3-(2-propenyloxy)-pyridine (intermediate (44).

The chemical industry reduces the impact on the environment during synthesis 96630-88-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Van Emelen, Kristof; De Bruyn, Marcel Frans Leopold; Alcazar-Vaca, Manuel Jesus; Andres-Gil, Jose Ignacio; Fernandez-Gadea, Francisco Javier; Matesanz-Ballesteros, Maria Encarnacion; Bartolome-Nebreda, Jose Manuel; US2004/19051; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, 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, Formula: C6H3F3INO, blongs to pyridine-derivatives compound. Formula: C6H3F3INO

To a solution of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (4.0 g, 13.8 mmol) in DMF (50 mL), CuCN (2.48 g, 27.7 mmol) was added. The mixture was degassed with 3 vacuum-nitrogen cycles and stirred at 120 C for 16 h. The reaction was cooled to room temperature, poured into water (60 mL), diluted with 3 M HC1 (30 mL) then extracted with EtOAc (3 x 80 mL). The combined organic layers were washed with brine (2 c 60 mL), dried over Na2S04, filtered, and concentrated to give 6-hydroxy-5-(trifluoromethyl)nicotinonitrile (2.5 g, crude) as an oil. 1H NMR (400 MHz, CDCI3): d 8.03 (s, 2H); MS: 189.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; HUDSON, Andrew R.; CHEN, Mi; NAGASAWA, Johnny Y.; (265 pag.)WO2019/241751; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 727356-19-6, 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 727356-19-6 as follows.

Potassium pthalimide (1.23 kg, 6.0 mol), potassium carbonate (2.07 kg, 15 mol) were dissolved in DMF (12.5L). A214.1a was added slowly and the reaction stirred at room temperature overnight. TLC analysis indicated disappearance of starting material. The product was filtered to yield A214.1 (2.5kg wet weight- used in next step without further drying).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,727356-19-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 204378-41-6, 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 204378-41-6, name is Methyl 6-chloro-4-methoxypicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 6-chloro-4-methoxypicolinate 25 (600 mg, 2.98 mmol) and cyclopentylzinc bromide (12 mL of a 0.5 M solution in THF) in dioxane (10 mL) Pd(dppf)Cl2 (25 mg, 30 mol) was added. The mixture was stirred at 75°C for 18 h. The mixture was cooled the rt and the reaction was quenched by carefully adding water (20 mL). The mixture was filtered and the filtrate was extracted with EA (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The crude product was purified by CC on silica gel eluting with heptane:EA 4:1 to give methyl 6-cyclopentyl-4-methoxypicolinate 30 (580 mg, ~80percent) as a pale yellow oil containing approx. 30percent of cyclopentyl 6-cyclopentyl-4-methoxypicolinate

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 204378-41-6, Methyl 6-chloro-4-methoxypicolinate.

Reference:
Article; Bolli, Martin H.; Lescop, Cyrille; Birker, Magdalena; De Kanter, Ruben; Hess, Patrick; Kohl, Christopher; Nayler, Oliver; Rey, Markus; Sieber, Patrick; Velker, Joerg; Weller, Thomas; Steiner, Beat; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 326 – 341;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 17322-91-7, name is 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one, molecular formula is C7H6N2O, 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. Quality Control of 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one

5-hydroxy -1H- pyrrolo [3,2] pyridine (10 mmol)Soluble in 40 ml of dichloromethane solution,Add 10 ml of triethylamine to it,Control temperature below 10 C,Add to the systema solution of 2-chloroacetyl chloride (12 mmol) in dichloromethane,After the addition is completed, return to room temperature.Stir at room temperature for 10 hours,The reaction system was then washed with 50 ml of a 5% aqueous solution of sodium carbonate.The organic phase is dried over anhydrous Na2SO4.After evaporating the solvent,The obtained solid is separated by flash column chromatography,Get 1.9 g light yellow2-Chloro-1-(5-hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-ethanone solid,The yield was 90%.

With the rapid development of chemical substances, we look forward to future research findings about 17322-91-7.

Reference:
Patent; Sang Qi; (10 pag.)CN108218865; (2018); A;,
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. 42182-27-4, name is 2-Amino-4-cyanopyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Amino-4-cyanopyridine

NaN02 (0.99 g, 14.3 mmol) was added in small portions to a well stirred solution of the product of Step B (0.96 g, 8.1 mmol) in a premixed solution of concentrated H2S04 (1 .2 ml) and H20 (1 1 .5 ml) while the temperature of the reaction mixture was kept at ) 0 – 5C. The clear solution became heterogenous with evolution of N2. The mixture was allowed to warm up to room temperature with stirring, than heated on the water bath (reflux) for 30 min and cooled to room temperature. The solid formed was filtered off, washed with H20 and dried in vacuo to give the title product (0.9 g, 92%) as colourless solid. 1 H NMR (DMSO-d6) 8.21 (d, 1 H, J = 2.4 Hz), 7.61 (dd, 1 H, 2.4, 9.6 Hz), 6.38 (d, 1 H, J = 9.6 Hz), 3.3 (broad s, 1 H + 2H20).

The synthetic route of 42182-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AKAAL PHARMA PTY LTD; GROBELNY, Damian W; GILL, Gurmit S; WO2014/63199; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem