Category: pyridine-derivatives

Electric Literature of 932-35-4, 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. 932-35-4, name is 3-Hydroxypicolinonitrile. A new synthetic method of this compound is introduced below.

(1) A suspension prepared by adding 2.73 g of 2-cyano-3-hydroxypyridine to 60 mL of a mixed solution of acetonitrile/water=5/1 was cooled to 0 C. A reaction mixture prepared by adding 4.85 g of N-bromosuccinimide slowly to the suspension was stirred for 2 hours under a nitrogen atmosphere. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with brine, then dried, and concentrated in vacuo to give 5.39 g of a crude product of 6-bromo-2-cyano-3-hydroxypyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,932-35-4, 3-Hydroxypicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; TEIJIN PHARMA LIMITED; KAWANA, Asahi; KANAZAWA, Chikashi; TERA, Masayuki; TAKAHASHI, Yoshimasa; IMAZEKI, Mariko; TAKAHASHI, Hiroyuki; TANOKURA, Akira; (51 pag.)US2016/39784; (2016); A1;,
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. 153034-80-1, name is 2-Fluoro-4-iodo-3-picoline. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 153034-80-1

A mixture of the product from the previous step (22 g, 93 mmol), Pd(OAc)2 (2.2 g, 9.8 mmol), l ,l’-bisdiphenylphosphino ferrocene (5.1 g, 9.2 mmol), and NaHC03 (46.7 g, 556 mmol) in MeOH (1 L) was stirred overnight in a CO atmosphere at 80 C. The mixture was cooled to room temperature, then water and sat. aq. (0516) NaHC03 solution were added. The mixture was then extracted with EtOAc. The organic layers was washed with saturated brine, and then dried over anhydrous sodium sulfate. The mixture was filtered and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (Petroleum ether : EtOAc = 4: 1) to give the title compound as a colorless oil (12 g, 77%).MS (ES+) C8H8FN02 requires: 169, found: 170 [M+H]+.

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, 153034-80-1, 2-Fluoro-4-iodo-3-picoline.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; JONES, Philip; CROSS, Jason; BURKE, Jason; MCAFOOS, Timothy; KANG, Zhijun; (154 pag.)WO2019/213318; (2019); 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.14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.SDS of cas: 14432-12-3

Under nitrogen protection, 2-chloropyridin-4-amine (301) (15 g, 0.116 mol, 1 eq) was dissolved in acetonitrile (200 mL) and heated to 70 C. in an oil bath, and then N-iodosuccinimide (NIS) (33 g, 0.139 mol, 1.2 eq) was added slowly. The reaction was stirred for 16 hours and cooled to room temperature. Saturated sodium thiosulfate solution was added until the reaction system turned to milk white. The pH of the reaction system was adjusted to 9-10 by an addition of saturated aqueous sodium carbonate solution and extracted with ethyl acetate (500 mL). The organic phase was separated which was washed with saturated brine (100 mL) twice, dried over anhydrous sodium sulfate, concentrated in vacuo and separated and purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=20/1) to obtain 2-chloro-5-iodopyridin-4-amine (23 g, yield: 78.1%). LCMS (ESI): m/z 255 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14432-12-3, 4-Amino-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; GUANGZHOU BEBETTER MEDICINE TECHNOLOGY CO., LTD.; CAI, Xiong; QIAN, Changgeng; LI, Junqi; QING, Yuanhui; WANG, Yanyan; XUE, Weicai; YOU, Huajin; (23 pag.)US2018/297995; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1008-91-9, 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. 1008-91-9, name is 1-(Pyridin-4-yl)piperazine, molecular formula is C9H13N3, 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.

809.9 g (3 mmol) of genistein, 60 ml of methanol, 240 muL (3 mmol) of 37% formaldehyde were added to a 100 ml round-bottomed flask, and stirred at 30 C. for 30 minutes under reflux.583.4 mg (3.6 mmol) of 1- (4-pyridyl) piperazine was added to a round bottom flask.Stir reflux at 35 C for 8h, and react at room temperature for 8h.The reaction was then stopped, suction filtered under reduced pressure, and solid-liquid separation.Collect the solid. The solid contains a small amount of 1-(4-pyridyl) piperazine.Formaldehyde and a small amount of genistein and products; the liquid contains genistein,1-(4-pyridyl)piperazine in methanol.Wash the solid 6 times with methanol, 10 ml of methanol each time,This gave 1022.8 mg of a white solid with a yield of 76.61%.

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 1008-91-9, 1-(Pyridin-4-yl)piperazine.

Reference:
Patent; Beijing Normal University; Yan Xi; Yu Meixuan; Song Jinglei; (16 pag.)CN110483465; (2019); A;,
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 1122-71-0, name is 6-Methyl-2-pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Methyl-2-pyridinemethanol

0411-1 Triethylamine (1 mL) was added to a solution of (6-methylpyridin-2-yl)methanol (302 mg) in tetrahydrofuran (5.8 mL) at room temperature, and methanesulfonyl chloride (0.28 mL) was added thereto at a temperature of from 0 C. to 5 C., followed by stirring at room temperature for 2 hours. The insolubles were filtered off using celite, and the solvent was distilled off under reduced pressure, thereby obtaining (6-methylpyridin-2-yl)methyl methanesulfonate (555 mg) as brown oily substance. MS m/z (M+H): 202.

With the rapid development of chemical substances, we look forward to future research findings about 1122-71-0.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); 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.113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.Formula: C6H4BrNO

Steps 1 To a mixture of 5-bromopyridine-3-carbaldehyde (XXXVIII) (6.00 g, 32.26 mmol, 1.0 eq), 3,3-difluoropyrrolidine (5.56 g, 38.71 mmol, 1.20 eq) and TEA (5.39 mL, 38.71 mmol, 1.2 Eq) in DCE (200 mL) was stirred at room temperature for 30 min, then added sodium triacetoxyborohydride (10.25 g, 48.38 mmol, 1.50 eq) in one portion at room temperature under N2. The mixture was stirred at room temperature for 6 hours. TLC showed the reaction was complete. The reaction was quenched with 1N NaOH (100 mL), extracted with DCE (100 mL*2). The combined organic layers were washed with brine (100 mL), dried and concentrated. The residue was purified by silica gel chromatography (column height: 50 mm, diameter: 50 mm, 300-400 mesh silica gel, DCM/MeOH=30/1?20/1) to give 3-bromo-5-((3,3-difluoropyrrolidin-1-yl)methyl) pyridine (XL): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). 1H NMR (CDCl3, 400 MHz) delta ppm 2.30 (spt, J=7.2 Hz. 2H), 2.75 (t, J=6.8 Hz, 2H), 2.91 (t, J=13.2 Hz, 2H), 7.85 (s, 1H), 8.45 (s, 1H), 8.59 (d, J=2 Hz, 1H); ESIMS found for CloHiiBrF2N2 m/z 277.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (262 pag.)US2016/68547; (2016); 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. 16063-69-7, name is 2,4,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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. category: pyridine-derivatives

n-BuLi (35 mL, 2.5 M in hexanes) was added dropwise to a stuffed solution of 2,4,6-trichloropyridine (15 g, 82.22 mmol, 1.00 equiv) in anhydrous THF (200 mL) at -78 C under nitrogen. After 30 minutes ethyl formate (10 mL, 215.31 mmol) was added at -78 C . The resulting solution was diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:10) to give the title compound (13 g, 75%) as a white solid. LC-MS(ES, mlz): 210 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 16063-69-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5825-71-8, 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 5825-71-8 as follows.

Reference Example 43-1 (R)-2-methyl-N-((R)-1-(pyrazolo[1,5-a]pyridin-2-yl)ethyl)propane-2-sulfinamide Pyrazolo[1,5-a]pyridine-2,3-dicarboxylic acid dimethyl ester (3.35 g, 14 mmol) was dissolved in 50% sulfuric acid (110 mL), and the solution was stirred for 2.5 hours at 80C. The reaction liquid was cooled to 0C, and a 8 M aqueous solution of sodium hydroxide was added thereto to adjust the pH to 9. Subsequently, the pH was adjusted to 3 with 6 M hydrochloric acid. A suspension liquid thus produced was separated by filtration, and crystals were washed with water and then dried under reduced pressure. Thus, pyrazolo[1,5-a]pyridine-2-carboxylic acid (pale brown crystals, 1.88 g, 81%) was obtained. In a nitrogen atmosphere, pyrazolo[1,5-a]pyridine-2-carboxylic acid (941 mg, 5.8 mmol) thus obtained was dissolved in THF (30 mL), and the solution was stirred for a while at room temperature. Subsequently, a THF solution of a borane-THF complex (20 mL, 18 mmol, 0.9 M) was added to the solution, and the mixture was stirred for 3.5 hours at 70C. The reaction liquid was cooled to 0C, water was added thereto, and the mixture was stirred for a while. Subsequently, 6 N hydrochloric acid was added thereto, and the mixture was heated to reflux for one hour. The solvent was distilled off under reduced pressure, subsequently methanol was added thereto, and the solvent was distilled off again. A residue thus obtained was diluted with ethyl acetate, and the organic layer was washed with a 1 N aqueous solution of sodium hydroxide, water, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, insoluble matters were filtered, and then the solvent was distilled off under reduced pressure. Thus, pyrazolo[1,5-a]pyridin-2-ylmethanol was obtained. According to a technique similar to that of Reference Example 13-3, pyrazolo[1,5-a]pyridine-2-carboaldehyde was obtained using pyrazolo[1,5-a]pyridin-2-ylmethanol thus obtained. According to a technique similar to that of Reference Example 1-2, (R)-2-methyl-N-(pyrazolo[1,5-a]pyridin-2-ylmethylene)propane-2-sulfinamide was obtained using pyrazolo[1,5-a]pyridine-2-carboaldehyde thus obtained and (R)-2-methylpropane-2-sulfinamide. According to a technique similar to that of Reference Example 1-3, the title compound (pale yellow oily material, 498 mg, 65%) was obtained using (R)-2-methyl-N-(pyrazolo[1,5-a]pyridin-2-ylmethylene)propane-2-sulfinamide thus obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5825-71-8, its application will become more common.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; Kinki University; TANAKA Hiroto; OOI Isao; MOGI Yuzo; HIROSE Masaaki; ENDO Tsuyoshi; OGAWA Toru; KAWABATA Atsufumi; (171 pag.)EP3404021; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 116118-99-1, 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid hydrochloride, 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: C8H10ClNO2S, blongs to pyridine-derivatives compound. Formula: C8H10ClNO2S

Synthesis Example 16c 4,5,6,7-Tetrahydro-thieno[3,2-c]pyridine 4,5,6,7-Tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid hydrochloride (260 mg, 1.2 mmol) was mixed with 47% hydrogen bromide aqueous solution (3 ml) and heated under reflux for 4 hours. The reaction solution was returned to room temperature and alkalified by adding sodium hydroxide aqueous solution (5 N), and the reaction product was extracted with diethyl ether, washed with saturated brine and then dried with anhydrous magnesium sulfate. By evaporating the solvent from the organic layer under a reduced pressure, 160 mg (1.1 mmol, 95% in yield) of the title compound was obtained. 1H-NMR (CDCl3): delta 2.80 (2H, t, J=5.6 Hz), 3.15 (2H, t), 3.93 (2H, t, J=1.7 Hz), 6.74 (1H, d, J=5.1 Hz), 7.07 (1H, d); MW 139.22 (C7H9NS); Mass spectrum EI-MS m/z 139 (M)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116118-99-1, 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Meiji Seika Kaisha, Ltd.; US6498251; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 93683-65-9, 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. 93683-65-9, name is 6-Chloro-3-nitropicolinonitrile. A new synthetic method of this compound is introduced below.

beta-chloro-S-nitro-pyridine-l-carbonitrile (100 mg, 0.54 mmol) is taken up in EtOH (1 niL), combined with SnCl2 (413 mg, 2.18 mmol) and heated to 900C for 3 h. Then the solvent is removed, the residue is taken up in ethyl acetate and first of all washed with NaHCO3 to pH 7, then washed with NaOH (2 M) to pH 8-9. Then the residue is filtered throughCelite, the filtrate is extracted again with ethyl acetate and the combined organic phases are dried on Na2SO4. The solvent is eliminated in vacuo and 3-amino-6-chloro-pyridine-2- carboxylic acid amide is obtained (HPLC-MS: tRet. = 0.78 min, MS(M+H)+ = 172, method LCMSBASl).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,93683-65-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; BOEHMELT, Guido; KOFINK, Christiane; KUHN, Daniel; MCCONNELL, Darryl; STADTMUELLER, Heinz; WO2010/7116; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem