Pyridine-derivatives

Application of 1122-72-1, 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. 1122-72-1, name is 6-Methyl-2-pyridinecarboxaldehyde, molecular formula is C7H7NO, 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.

(i) 6-Methyl-2-hydroxymethylpyridine 6-Methylpyridine-2-carboxaldehyde (0.44 mmole) in 50 ml methanol was reduced with 20.6 mmole sodium borohydride at 0-5 C. After reduction was complete, the mixture was neutralized (pH 7.5) with 2N sulfuric acid, filtered, the filtrate concentrated and partitioned between chloroform and water. Evaporation of solvent from the organic layer gave 3.32 g of red-black oil which was used in the next step.

According to the analysis of related databases, 1122-72-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US4826833; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 36953-37-4, 4-Bromopyridin-2(1H)-one, 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, name: 4-Bromopyridin-2(1H)-one, blongs to pyridine-derivatives compound. name: 4-Bromopyridin-2(1H)-one

Sodium chloro(difluoro)acetate (5.26 g, 34.5 mmol) and potassium carbonate (3.57 g, 25.8 mmol) were added to a solution of 4-bromopyridin-2(1 /-/)-one (3.00 g, 17.2 mmol) in /V,/V-dimethylformamide (30 mL), and the reaction mixture was stirred at 95 C for 2 hours. Water (100 mL) was added, and the resulting mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed sequentially with water (200 mL) and with saturated aqueous sodium chloride solution (150 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Eluent: 15: 1 petroleum ether / ethyl acetate) afforded the product as a pale yellow oil. Yield: 1.5 g, 6.7 mmol, 39%. 1H NMR (400 MHz, CDCI3) delta 8.04 (d, J=5.5 Hz, 1H), 7.44 (t, JHF=72.6 HZ, 1H), 7.27 (dd, J=5.4, 1.6 Hz, 1H), 7.12 (br d, J=1.5 Hz, 1H).

The synthetic route of 36953-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BECK, Elizabeth Mary; BRODNEY, Michael Aaron; BROWN, Matthew Frank; BUTLER, Christopher Ryan; GILBERT, Adam Matthew; LACHAPELLE, Erik Alphie; MCALLISTER, Laura Ann; UCCELLO, Daniel Paul; ZHANG, Lei; (140 pag.)WO2018/234953; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65169-42-8, 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 65169-42-8, name is Methyl 6-chloro-5-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 3; 5-Formyl-3-methyl-2-pyridinecarbonitrile (Used to prepare Example 32) (a) (6-Chloro-5-methyl-3-pyridinyl)methanolTo a solution of methyl 6-chloro-5-methyl-3-pyridinecarboxylate (84 mg, 0.453 mmol) in DCM (2 ml), DIBAL-H (1.5 M solution in toluene, 0.905 ml, 1.358 mmol) was added dropwise under N2 at -78 C. The reaction mixture was allowed to attain rt and stirred overnight. After 18 h, TLC showed no starting material. The reaction was quenched by addition of sodium-potassium tartrate saturated solution, extracted with DCM, dried, filtered, and concentrated to afford (6-chloro-5-methyl-3-pyridinyl)methanol (63 mg, 0.400 mmol, 88% yield) pure enough to be used in the next step.1H-NMR (delta ppm, CDCl3): 8.17 (s, 1H), 7.60 (s, 1H), 4.69 (s, 2H), 2.37 (s, 3H).

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 65169-42-8, Methyl 6-chloro-5-methylnicotinate.

Reference:
Patent; Alemparte-Gallardo, Carlos; Barfoot, Christopher; Barros-Aguirre, David; Cacho-Izquierdo, Monica; Fiandor Roman, Jose Maria; Hennessy, Alan Joseph; Pearson, Neil David; Remuinan-Blanco, Modesto Jesus; US2009/306089; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3279-76-3 , The common heterocyclic compound, 3279-76-3, name is 6-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, 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.

Step A. 2-Methoxy-6-methyl-pyridine. To a mixture of 6-methyl-pyridin-2-ol (10.0 g, 91.6 mmol) and Ag2CO3 (34.5 g, 125.1 mmol) in CHCl3 (300 mL) was added Mel (64.4 mL, 1.04 mol) over 30 min. The mixture was stirred for 48 h at rt in the dark, then was filtered through a pad of SiO2, washing with Et2O. The filtrate was concentrated to provide the title compound (9.03 g, 80%). MS (ESI): mass calcd. for C7H9NO, 123.07; m/z found, 124.3 [M+H]+. 1H NMR (CDCl3): 7.46-7.41 (m, 1H), 6.70 (d, J=7.2, 1H), 6.53 (d, J=8.2, 1H), 3.91 (s, 3H), 2.44 (s, 3H).

The synthetic route of 3279-76-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Carruthers, Nicholas I.; Keith, John M.; Letavic, Michael A.; Shah, Chandravadan R.; US2006/287292; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1221171-70-5, 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 1221171-70-5 as follows.

To a solution of 2-chloro-6-(trifluoromethoxy)pyridine (5.0 g, 25.3 mmol, 1 equiv) in MeOH (120 mL) was added triethylamine (7.7 g, 75.9 mmol, 10.5 mL, 3.00 eq) and Pd(dppf)Cl2 (930 mg, 1.27 mmol, 0.05 equiv). The suspension was degassed and purged with CO several times. The mixture was stirred at l00C under CO (50 Psi) for 48 hours. The reaction mixture was cooled to 20C and concentrated in vacuo. The residue was purified by silica gel chromatography (eluted with PE/EtOAc = 10/1) to afford the title compound methyl 6-(trifluoromethoxy)picolinate as a yellow oil (3.85 g, 68% yield). LC-MS: m/z 222.0 (M+H) +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221171-70-5, its application will become more common.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1221171-70-5, 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. 1221171-70-5, name is 2-Chloro-6-(trifluoromethoxy)pyridine. A new synthetic method of this compound is introduced below.

2-Bromo-6-trifluoromethoxypyridine (55); A solution of 2-chloro-6-trifluoromethoxypyridine (2, 7.0 g, 35.4 mmol) in hydrobromic acid (33% in acetic acid, 100 mL) was heated for 3 days at 100 0C. The reaction mixture was cooled down to 0 0C before being slowly neutralized by addition of saturated aqueous solution of sodium hydrogencarbonate (500 mL). After extraction with ethyl acetate (4 x 100 mL), the combined organic layers were dried over sodium sulfate before being evaporated. The crude oil was distilled under vacuum (67-69 0C / 15 mbar) to afford pure 2-bromo-6-trifluoromethoxypyridine (2, 4.2 g, 17.3 mmol, 48%) as a colorless oil.1H NMR (CDCl3, 300 MHz): delta = 7.58 (t, J = 7.9 Hz, 1 H), 7.37 (d, J = 7.7, 1 H), 6.92 (d, J = 8.0, 1 H). – 19F NMR (CDCl3, 282 MHz): delta = -56.5 – 13C NMR (CDCl3, 75MHz): delta = 154.5, 141.0, 138.1, 125.1, 119.0 (q, J= 260 Hz), 110.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (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. 62150-47-4, name is Ethyl 4-bromopicolinate, molecular formula is C8H8BrNO2, 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. COA of Formula: C8H8BrNO2

At a temperature of less than 40 C,Dissolve 1300 g of Cpd 2 in 7 L of ethanol.Add 400g of sodium borohydride in batches,Stir at room temperature overnight;2N hydrochloric acid was added dropwise at a temperature of less than 20 C to adjust the pH to weakly alkaline,Rotate most of the ethanol,add water,Adjusted to strong alkaline with potassium carbonate,Extracted with ethyl acetate (EA),Wash the product to the aqueous phase with 1N hydrochloric acid.Extracted with EA,The aqueous phase is added with potassium carbonate to adjust to strong alkalinity,EA extraction, sodium chloride washing,Dry over anhydrous sodium sulfate and spin dry.Through the column, 4-bromopyridine-2-methanol (Cpd 3) 650 g was obtained. The yield was 62%.

With the rapid development of chemical substances, we look forward to future research findings about 62150-47-4.

Reference:
Patent; Tianjin Quan He Cheng Science And Technology Co., Ltd.; Song Yanmin; Wan Jiaqiang; Li Weide; (11 pag.)CN108516953; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 670253-37-9 ,Some common heterocyclic compound, 670253-37-9, molecular formula is C5H4ClIN2, 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.

In a one-neck round bottom flask, 90.7 g (357.1 mmol) of a 1F compound was added to 500 ml of NMP, and 21.4 g (182.1 mmol) of Zetan(CN)2 was added, followed by rapid addition of 41 g (35.7 mmol) of Pd(PPh3)4, 135 C reaction for 5h. The reaction was completed to give a brown oily liquid. The mixture was slowly poured into 3 L of ice water under stirring, and a large amount of a tan solid was precipitated, which was filtered, washed with water and dried to give Compound 1G

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,670253-37-9, its application will become more common.

Reference:
Patent; Chengdu Huajian Pending Technology Co., Ltd.; Zhang Lei; (14 pag.)CN109928968; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1440519-73-2, 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.1440519-73-2, name is 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, molecular formula is C15H13ClN2O2, molecular weight is 288.7289, as common compound, the synthetic route is as follows.

To a solution of 2-chloro-6-(4-methoxy-benzyl)-6,7-dihydro-pyrrolo [3 ,4-b]pyridin-5-one (5.8 g, 20.0 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 1.7 g, 42.0 mmol) at room temperature. The resulting reaction mixture was stuffed for 30 mmbefore iodomethane (6.0 g, 42.0 mmol) was added. After stirring at room temperature overnight, the mixture was quenched with water and extracted with EtOAc. The organic layer was then washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give the crude product which was then purified by flash column chromatography (silica gel 20 g, 5% to 20% ethyl acetate in DCM). The title compound was obtained (3.8 g, 57%) as a white solid. MS: 316.2 (M+Hj.

Statistics shows that 1440519-73-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LI, Dongbo; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; WU, Jun; ZHOU, Mingwei; WO2014/191336; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69422-72-6, 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.69422-72-6, name is 2,4,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, molecular weight is 226.4446, as common compound, the synthetic route is as follows.

To 1.7 (1.0 g, 4.42 mmol, 1.0 eq) was added SOCl2(5.0 mL) followed by DMF (catalytic) and reflux ed for 16 h. Reaction mixture was concentrated under reduced pressure to obtain acyl chloride. Methyl hydrazine (0.20 g, 42.5 mmol, 1.0 eq) was dissolved in CH2C12(20.0 mL) followed by addition of solution of NaOH (0.72 g, 177 mmol, 4.0 eq) in water (5.0 mL). To the solution was added previously made acyl chloride solution in CH2C12(20.0 mL) dropwise. Reaction mixture was refluxed for 15 min. After completion of reaction, reaction mixture was transferred into water and extracted with CH2C12. Organic layers were combined, washed with brine, dried over Na2S04and concentrated under reduced pressure to pressure to obtain crude which was purified by column chromatography to provide 1.8. (1.1 g, 97.0 %). MS(ES): m/z 255.5 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 69422-72-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem