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. 889939-26-8, name is 4-Bromo-2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C13H8BrIN2O2S

A sealed tube containing a suspension of 5-(2~iodo-1-(phenylsulfonyl)- 1 H-pyrrolo[2,3-b]pyridn-4-yl)-2-((tetrahydrQ-2H-pyran-4-yl)oxy)benzonitrile (100 mg, 0.171 mmol) and Pd(PPh?)4 (9 mg, 0.008 mmol) in a degassed mixture of dioxane/H20 (1.5mL, 4/1 ), was preheated at 85 C for 5 rnin. Next, K2C03 (59 mg, 0.43 mmol) and 2- (3,6-dhydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (54 mg, 0.257 mmol), were added to the mixture and the reaction was additionally heated at 100 C in the sealed tube for 15 hrs. Afterwards, the crude material was allowed to reach room temperature. It was concentrated to dryness; the residue was triturated with EtOH and filtered through a short pad of Celite, washing the solids with CH2CI2. The filtrate was concentrated to dryness. The residue was purified by flash column chromatography on silica gel to afford 5-(2-(3,6-dihydro-2H-pyran-4-yl)-1- (phenylsulfonyl)-l H-pyrroio [2,3-b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4- yl)oxy)benzonitrile. LCMS-ESI+ (m/z): [M+H]+ calcd for C30H27N3O5S: 542.2; found: 542.2

The synthetic route of 889939-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; DU, Zhimin; GUERRERO, Juan, Arnaldo; KAPLAN, Joshua, Aaron; KNOX, JR., John Edward; NADUTHAMBI, Devan; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William, J.; ZABLOCKI, Jeff; WO2015/187684; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 59237-53-5, Adding some certain compound to certain chemical reactions, such as: 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate,molecular formula is C7H5ClN2O4, 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 59237-53-5.

A suspension of methyl beta-chloro-S-nitronicotinate (1 eq), iron powder (5.2 eq), and NH4Cl3 (5.3 eq) in MeOH was heated at 75°C for 2 h. The mixture was passed through a pad of celite while hot and concentrated in vacuo to give methyl 5- amino-6-chloronicotinate (56 percent yield)

According to the analysis of related databases, 59237-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; OALMANN, Christopher; DISCH, Jeremy, S.; NG, Pui, Yee; PERNI, Robert, B.; WO2010/71853; (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.103999-77-5, name is 2,5-Dichloro-3-fluoropyridine, molecular formula is C5H2Cl2FN, molecular weight is 165.98, as common compound, the synthetic route is as follows.Product Details of 103999-77-5

(c) 5-chloro-2,3-difluoropyridine A suspension of 64.6 g (1.1 mol) of potassium fluoride and 11.25 g (0.075 mol) of cesium-fluoride in 240 ml of sulfolane (1,1-dioxo-tetrahydrothiophene) is heated to 140 C. By reducing the pressure 50 ml of sulfolane are distilled off. To the suspension a solution of 61.4 g (0.37 mol) of 2,5-dichloro-3-fluoropyridine in 20 ml of sulfolane is added. The reaction-mixture is then stirred for 35 hours at a temperature of 140, cooled and poured into ice/water. The organic material is extracted with ether. The ethereal layer is washed with water dried over magnesium sulfate, filtered and evaporated to yield 48.7 g of a colourless oil (88% of the theory) which boils at 65-66 at 133 mbar.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103999-77-5, 2,5-Dichloro-3-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Ciba Geigy Corporation; US4713109; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65515-28-8, Methyl 2,6-dichloronicotinate, 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, Application In Synthesis of Methyl 2,6-dichloronicotinate, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 2,6-dichloronicotinate

A 250 mL eggplant flask was sequentially charged with methyl 2,6-dichloronicotinate (3.09 g, 15 mmol), 4-methoxyphenol (1.86 g, 15mmol), and 18 mL of N, N-dimethylformamide for dissolving them. Triethylamine (2.7 ml, 19.5mmol) was added dropwise under stirring at room temperature, and after completion of the dropwise addition, triethylenediamine (252 mg, 2.25 mmol) was added. The mixture was stirred at room temperature for 4-5 hours and the solutionchanged from clear to turbid. Thin layer chromatography [V (petroleum ether) / V (ethyl acetate) = 6/1] detected thatmost of the raw material disappeared. Then, 1.30 mL of HOAc, 25 mL of isopropanol and 15 mL of ice water weresequentially added while the solution changed from turbid to clear, and stirred at room temperature for 0.5 hour. 40 mLof water was slowly dropwise added, and after completion of the dropwise addition, stirred at room temperature for 2hours. A large number of white solid precipitated and was filtered. The filter cake was washed with a mixed solution ofisopropyl alcohol / water = 1: 1 and dried under vacuum at 50 C for 8 hours to obtain 4.05 g of methyl 2-chloro-6-(4-methoxyphenoxy) nicotinate as a solid, 91.84%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65515-28-8, Methyl 2,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Shenyang Sunshine Pharmaceutical Co., Ltd.; ZHOU, Yunlong; CAI, Suixiong; WANG, Guangfeng; JIAO, Lingling; MIN, Ping; JING, Yu; GUO, Ming; (44 pag.)EP3275881; (2018); 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. 6969-71-7, name is [1,2,4]Triazolo[4,3-a]pyridin-3(2H)-one, the common compound, a new synthetic route is introduced below. name: [1,2,4]Triazolo[4,3-a]pyridin-3(2H)-one

Firstly, 1.35 g (10 mmol) of 1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one (1), 2.5 cm3 (26 mmol) of1-bromo-3-chloropropane (2a), 322 mg (1 mmol) of TBAB, 8.28 g (60 mmol) of K2CO3, and 5 cm3 ofacetonitrile were placed in a conical flask. The reactions were carried out under microwave radiation(Samsung M182DN; 300 W) for 50 s. After this time, 2.3 g (10 mmol) of 1-(3-chlorophenyl)piperazine hydrochloride (4) and 5 cm3 of acetonitrile were added to the reaction mixture. Reactions were carriedout in the presence of microwave radiation for another 90 s. The progress of the reaction was monitoredby TLC (eluent chloroform-methanol 9:1). After the reaction, 50 cm3 of water was added and theresulting product was filtered o on a Buechner funnel. Yield (Samsung M182DN; 300 W) 31%, yield(CEM Discover SP reactor; 100 W) 71%.

The synthetic route of 6969-71-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jaskowska, Jolanta; Zar eba, Przemys?aw; Sliwa, Pawe?; Pindelska, Edyta; Sata?a, Grzegorz; Majka, Zbigniew; Molecules; vol. 24; 8; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 947249-14-1, 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.947249-14-1, name is 3-(Difluoromethoxy)pyridin-2-amine, molecular formula is C6H6F2N2O, molecular weight is 160.1215, as common compound, the synthetic route is as follows.

To a solution of 3-(difluoromethoxy)pyridin-2-amine (2.3 g, 14.36 mmol) in acetonitrile (15 was added N-bromosuccinimide (2.61 g, 14.65 mmol) over 3 min at 0 C. The reaction mixture was stirred at the same temperature for another 20 min and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 60 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20% ethyl acetate in hexane) affording 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 93%): NMR (400 MHz, DMSO-d6) delta 7.89 (s, 1H), 7.51 (s, 1H), 7.16 (t, / = 73.6 Hz, 1H), 6.34 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 947249-14-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); 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. 153034-90-3, name is 2-Chloro-4-iodonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Chloro-4-iodonicotinaldehyde

Step 1. 2-chloro-4-iodonicotinonitrileTo 2-chloro-4-iodonicotinaldehyde (1.0 g, 3.7 mmol) dissolved in THF (11 mL) was added ammonium hydroxide (11 mL, 280 mmol) followed by iodine (1040 mg, 4.11 mmol), the reaction was held at ambient temperature 3.5 h, color visibly lightens as reaction progresses until the end when it is nearly colorless. LCMS indicates reaction to be complete. Reaction was quenched by addition of saturated NaHSO3, extracted into EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the crude product, 926 mg. Dissolved in CHCl3/MeOH and applied to 120 g silica gel column, the product fractions were concentrated in vacuo to give 728 mg product. The purified material was taken directly to next step.

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, 153034-90-3, 2-Chloro-4-iodonicotinaldehyde.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 586-95-8, 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.586-95-8, name is 4-Pyridinemethanol, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.

(l-Benzyl-l,2,3,6-tetrahydropyridin-4-yl)methanol. 4-Hydroxymethyl- pyridine (20 g, 183 mmol, 1.0 eq) was dissolved in DMF (80 mL) andbenzylbromide (24.2 mL; 202 mmol) was added and the solution was stirred at 100 C for 2 hours. The solution was allowed to cool to RT and diluted with EtOH (300 mL) and treated portionwise with NaBH4 (8.7 g; 230 mmol) and stirred at reflux for 3 hours. The solution was allowed to cool to RT and concentrated largely. The residue was taken up in EtOAc and water and the organic phase was dried (Na2S04), filtered and concentrated to give 35 g crude oil. The material was purified with a short plug (10 cm) of silica eluting with EtOAc to give the product (23.9 g; 64%) which was isolated as an oil. NMR (300 MHz, CDC13) delta ppm 7.39-7.2 (m, 5H), 5.69-5.63 (m, 1H), 4.03 (s, 2H), 3.58 (s, 2H), 3.0 (m, 2H), 2.6 (t, J= 6 Hz, 2H), 2.21-2.11 (m, 2H).

Statistics shows that 586-95-8 is playing an increasingly important role. we look forward to future research findings about 4-Pyridinemethanol.

Reference:
Patent; ABBOTT HEALTHCARE PRODUCTS B.V.; STOIT, Axel; IWEMA BAKKER, Wouter, I.; COOLEN, Hein K.A.C.; VAN DONGEN, Maria J.P.; LEFLEMME, Nicolas J.-L.D.; WO2012/4378; (2012); 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 98400-69-2, name is 4-(Boc-Amino)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H14N2O2

A 500 rnL two-necked round bottom flask equipped with nitrogen inlet adaptor and magnetic stirring bar was charged with tert-butyi pyridin-4-ylcarbamate (3.88 g, 20.0 mmol, prepared as described in Spivey, A. C. et al. J. Org. Chem. 64, pp. 9430-9443 (1999)), lambdaWlambda^-tetramethylethylenediamine (TMEDA) (8.15 mL, 54.0 mmol), and anhydrous tetrahydrofuran (THF) (10 mL). The resultant clear, colorless solution was degassed with several cycles of evacuation under reduced pressure followed by a nitrogen purge, then cooled to -78 0C with a dry ice/acetone bath. A solution of n-butyllithium in hexanes (20.0 mL of a 2.5 M solution, 50.0 mmol) was added via syringe under nitrogen atmosphere over 15 minutes (min), resulting in the formation of a thick tan slurry. After 10 min, the cooling bath was replaced with a 5 0C ice bath, and the slurry was allowed to stir for 2 hours. The slurry was then cooled again to -78 0C, and triisopropylborate (17.5 mL, 76.0 mmol) was added dropwise via syringe over 10 min. The reaction mixture was then warmed to ambient temperature and allowed to stir for 20 min. The reaction mixture initially became clear, and then a white precipitate formed. The resultant slurry was then poured into saturated aqueous ammonium choride (100 mL) and allowed to stir vigorously for an additional 20 min. The white precipitate was isolated by filtration, washed sequentially with water (100 mL) and diethyl ether (100 mL), and then dried overnight under reduced pressure, providing 3.10 g of 4-[(tert-butoxycarbonyl)amino]pyridin-3- ylboronic acid as a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 98400-69-2.

Reference:
Patent; COLEY PHARMACEUTICAL GROUP, INC.; WO2007/143526; (2007); A2;,
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. 13600-47-0, name is 5-Aminonicotinonitrile, molecular formula is C6H5N3, 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. Application In Synthesis of 5-Aminonicotinonitrile

(S)-4-Bromo-2,2-difluoro-7-((trifluoromethyl)sulfonyl)-2,3-dihydro-1H-inden-1-ol (23 mg, 0.060 mmol) was dissolved in 1,4-dioxane (0.20 mL) and treated with 3-pyridinecarbonitrile, 5-amino- (8.6 mg, 0.070 mmol), cesium carbonate (27.5 mg, 0.080 mmol), palladium (II) acetate (0.68 mg, 0.003 mmol), and Xantphos (3.5 mg, 0.010 mmol). After cooling, the mixture was diluted with water and ethyl acetate then separated. This mixture didn’t separate well and there was insoluble yellow solid present, which was removed by filtration. The aqueous was washed with ethyl acetate and the combined organics were washed with saturated NaHCO3, saturated NaCl, dried over Na2S04, and concentrated in vacuo to a dark residue. The crude material was chromatographed on Si02 eluting with a gradient of ethyl acetate / hexane. The product was recovered as light tan solid, (12 mg, 47%). LCMS ESI (+) m/z (M+H) 420; 1H MR (400 MHz, CDCl3 plus CD3OD): delta 8.66 (s, 1H), 8.60 (s, 1H), 7.79-7.75 (m, 2H), 7.22-7.20 (m, 1H), 5.30 (d, 1H), 3.92-3.90 (m, 1H), 3.46-3.32 (m, 1H), 3.31-3.21 (m, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 13600-47-0.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; JOSEY, John, A.; (281 pag.)WO2016/145045; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem