Category: pyridine-derivatives

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. 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol, the common compound, a new synthetic route is introduced below. Recommanded Product: (6-(Trifluoromethyl)pyridin-2-yl)methanol

Step 3; (6-Trifluoromethylpyridin-2-yl)methanol (760 mg, 4.3 mmol) was dissolved in CH2Cl2 and thionyl chloride was added slowly at room temperature. The reaction mixture was stirred at room temperature for 4 h. Solvent was removed under the reduced pressure, the pH was adjusted to 5, and the product was extracted with EtOAc. Purification by flash column ( 5% EtOAc-Hexane) gave 2-chloromethyl-6-trifluoromethylpyridine (200 mg) as a white solid.

The synthetic route of 131747-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2006/34004; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1095823-39-4, Adding some certain compound to certain chemical reactions, such as: 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine,molecular formula is C6H4ClF3N2, 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 1095823-39-4.

Synthesis of Compound S.7. To a solution of S.6 (205 mg, 0.64 mmol) in methylene chloride (4 mL) at rt was added oxalyl chloride (160 muL, 0.0019 mol) followed by the addition of DMF (50 muL) and stirred at RT for 1 hr. Separately a solution of A.6 (132 mg, 0.000672 mol), acetonitrile (2 ml) and pyridine (520 muL, 0.0065 mol) was stirred at RT followed by the addition of chlorotrimethylsilane (100 muL, 0.0008 mol). The acid chloride was concentrated under reduced pressure to a tan solid and redissolved in acetonitrile (2 mL). To the acid chloride solution was added the activated aniline. After 3 hr, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with dilute citric acid (50 mL), aqueous sodium bicarbonate (50 mL) and water. The organic layer was dried over sodium sulfate and concentrated to a residue which was purified by to give compound S.7. MS m/z: 498.95 [M+1]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); 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.1074-98-2, name is 3-Methyl-4-nitropyridine 1-oxide, molecular formula is C6H6N2O3, molecular weight is 154.13, as common compound, the synthetic route is as follows.HPLC of Formula: C6H6N2O3

[0334] 3-Methyl-4-nitropyridine 1-oxide (24.1a, 12.0 g, 0.07786 mol) was dissolved in acetyl chloride (60.00 mL). The reaction was heated to reflux for 2 hours. After cooling the reaction was poured onto ice and was basified with anhydrous sodium carbonate and extracted with chloroform. The extract was dried with potassium carbonate and filtered. The chloroform was evaporated off to yield the desired product in high purity. (85% yield) The MP was taken and found to be at 124 C, which matches literature references.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1074-98-2, 3-Methyl-4-nitropyridine 1-oxide, and friends who are interested can also refer to it.

Reference:
Patent; ADOLOR CORPORATION; WO2008/63625; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 182181-42-6, 2-(Chloromethyl)-8-methylimidazo[1,2-a]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, 182181-42-6, blongs to pyridine-derivatives compound. SDS of cas: 182181-42-6

67(D) 8-Methyi-2-(4-(trimethyisiiyi)but-3-ynyl)-imidazo[1,2-a]pvridine ;To a solution of trimethyl(prop-1-ynyl)silane (259 mg, 2.31 mmol) in THF (7.5 mL) at -78C was added n-BuLi 2.5M in hexane (1.1 mL, 2.8 mmol). After 90min at -78C 2-(chloromethyl)-8-methyl-imidazo[1,2-a]pyridine (500 mg, 2.8 mmol) in THF (5 mL) was added dropwise. The solution became blue-green at-78C. The solution was stirred at-78C for an additional 1h. The reaction was quenched with water and the solvent was removed under reduced pressure. The crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent) to afford 590 mg of 8-methyl-2-(4-(trimethylsilyl)but-3-ynyl)- imidazo[1,2-a]pyridine (Yield : 100%) as an yellow oil. LCMS (RT) : 0.59-2.61min; MS (ES+) gave m/z : 257.1 Rf (DCM/MeOH : 95/5) : 0.22

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,182181-42-6, its application will become more common.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2005/123703; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6945-67-1 ,Some common heterocyclic compound, 6945-67-1, 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.

Combine 2-bromo-4-nitropyridine (1.00g, 4.93mmol), 4-methylpiperidin-4-ol(709.23mg, 6.16mmol) and cesium carbonate(2.41g, 7.39mmol) dissolved in 30mL In 1,4-dioxane solution, react overnight at 100C. LC-MS detection, the reaction is over,Cool to room temperature, filter, concentrate the filtrate and purify by column chromatography to obtain the title compound.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6945-67-1, 2-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Wang Yazhou; Quan Xu; Liu Haixuan; Wang Xiaowei; Zhang Yan; Li Xue; Cao Chen; Guo Zhuang; Lv Kunzhi; Wang Hai; Zheng Guochuang; (126 pag.)CN111196804; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 386704-06-9 , The common heterocyclic compound, 386704-06-9, name is 2-Chloro-6-(trifluoromethyl)nicotinonitrile, molecular formula is C7H2ClF3N2, 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.

2-Chloro-6-(trifluoromethyl)nicotinonitrile (340 mg, 1.65 mmol) was diluted with toluene (2.0 rnL), placed under nitrogen and cooled to -78C. DIBAL-H (3292 mul, 3.29 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 00C and acetic acid (1 mL) was added followed by 5 mL of water. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle’s salt, dried over MgSO4, filtered and concentrated. The material was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes to yield the desired compound(115 mg, 0.549 mmol, 33.3 % yield) as a clear oil.

The synthetic route of 386704-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1227573-02-5, 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.1227573-02-5, name is 3-Bromo-5-fluoroisonicotinaldehyde, molecular formula is C6H3BrFNO, molecular weight is 204, as common compound, the synthetic route is as follows.

To a solution of 3-bromo-5-fluoroisonicotinaldehyde (5.0 g, 24.5 mmol, 1.0 eq) in DME (25.0 mL) was added Eta2 Eta220 (25.0 mL) and the reaction mixture was heated at 110 C overnight. After the reaction was complete, the solvent was concentrated. The resulting residue was diluted by water, extracted by EA (100.0 mL X 3), washed by brine, dried over Na2S04, concentrated. The resulting residue was purified by column chromatography (PE: EA = 2: 1) to provide 4-bromo-lH-pyrazolo[3,4-c]pyridine (1.5 g, 31.3%) as a white solid. LCMS (M+H+) m/z calculated 198.1, found 198.2.

The chemical industry reduces the impact on the environment during synthesis 1227573-02-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 160590-36-3, name is 2-Methoxy-3-nitro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Methoxy-3-nitro-4-methylpyridine

BrSodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4-methyl-3-nitropyridine (250 g, 1.49 mol) in acetic acid (1.5 L) at ambient temperature, then bromine (639g, 4.00 mol) was added and the reaction was heated at 80 C for 12 h. The mixture was then quenched by the addition of 10% aqueous NaOH (1.5 L) and saturated aqueous Na2SO3 (1.5 L) at 0 C. The resulting solid was collected by filtration and washed with water, dried under vacuum to give the title compound (302 g, 82.2% yield) as a light yellow solid. ?H NMR (400MHz, DMSO-d6): oe 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 160590-36-3.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ADLER, Marc; BURDICK, Daniel, J.; CRAWFORD, Terry; DUPLESSIS, Martin; MAGNUSON, Steven; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TSUI, Vickie Hsiao-Wei; WANG, Shumei; (276 pag.)WO2016/123391; (2016); 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. 201937-23-7, name is 6-Chloronicotinimidamide hydrochloride. A new synthetic method of this compound is introduced below., name: 6-Chloronicotinimidamide hydrochloride

2-(6-chloropyridin-3-yl)-4-(2-methoxyethoxy)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (O-l) A suspension of 1-tert-butyl 3 -ethyl 4-oxopiperidine-l,3-dicarboxylate (A-I, 41.5 g, 153 mmol), -chloropyridine-S-carboximidamide hydrochloride (43.9 g, -85% pure, 194 mmol), and K2CO3 (59.8 g, 433 mmol) in DMF (457 mL) was treated with 2-bromoethyl methyl ether (26.3 ml, 280 mmol) with stirring. The mixture was heated to 65 ºC and stirred for 24 hr, adding additional small equivalents of 2-bromoethyl methyl ether and K2CO3 to drive reaction to completion if needed. The reaction mixture was diluted with EtOAc (1.5 L), and washed with water (2 L), sat. aq. NaHCO3 (2 L), water (2 L), and brine (1 L). The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to provide unpurified Boc-protected intermediate (~62 g), which was used in the subsequent step without further purification.

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, 201937-23-7, 6-Chloronicotinimidamide hydrochloride.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
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. 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine, molecular formula is C6H5BrFN, 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. Product Details of 100202-78-6

Dissolve (+/-)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile (6.88 g, 21.0 mmol) and 2-bromomethyl-6-fluoro-pyridine (3.99 g, 21.0 mmol) in DMF (80 mL). Add cesium carbonate (7.51 g, 23.1 mmol, 1.10 equivalents) and stir the reaction mixture at room temperature under nitrogen for 48 h. Dilute the reaction with ethyl acetate, wash with water (3×), dry over anhydrous sodium sulfate, filter, and concentrate to obtain a semi-solid (8.10 g). Purify the crude product on a 120 g silica gel column eluting with 0 to 100% ethyl acetate/hexanes to obtain 6.7 g of a tan/brown solid. Suspend the product in ether (100 mL) at room temperature overnight. Filter the solid, rinse with ether, and dry under high vacuum to obtain the title compound as a tan solid (5.70 g, 62%). LCMS 437.1 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 100202-78-6.

Reference:
Patent; Gavardinas, Konstantinos; Green, Jonathan Edward; Jadhav, Prabhakar Kondaji; Matthews, Donald Paul; US2010/69404; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem