Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 10165-86-3, Methyl 6-formylnicotinate, 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, 10165-86-3, blongs to pyridine-derivatives compound. COA of Formula: C8H7NO3

A mixture of methyl 6-formylnicotinate (1.000 g, 6.055 mmol) and 3-chloro-4-fluoroaniline (0.970 g, 6.66 1 mmol) in tetrahydrofuran (50 mL) was stuffed at the room temperature for 30 mm, and treated with sodium triacetoxyborohydride (1.925 g, 9.083 mmol). The reaction mixture was stuffed at the same temperature for additional 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / dichloromethane = 0 percent to 5 percent) to give methyl6-(((3-chloro-4-fluorophenyl)amino)methyl)nicotinate as brown solid (0.510 g, 28.6percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10165-86-3, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); 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.884494-34-2, name is 2-Ethynyl-5-fluoropyridine, molecular formula is C7H4FN, molecular weight is 121.11, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Step 3: Preparation of ethyl 5-(5-fluoropyridin-2-yl)isoxazole-3-carboxylate To a solution of 2-ethynyl-5-fluoropyridine (1.5 g, 12.4 mmol) in N,N-dimethylformamide (20 mL) at 23 C. was added (Z)-Ethyl 2-chloro-2-(hydroxyimino)acetate (2.81 g, 18.6 mmol). The reaction mixture stirred for 1 h before triethylamine (1.88 g, 18.6 mmol) was added. The mixture was heated at 90 C. for 16 h. The mixture was diluted with brine (100 mL), extracted with ethyl acetate (100 mL*2) and purified by column chromatography (silica, petroleum ether/ethyl acetate=20/1) to give ethyl 5-(5-fluoropyridin-2-yl)isoxazole-3-carboxylate (300 mg, 1.27 mmol, 10%) as a gray oil. LCMS (ESI) m/z: 237.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-34-2, 2-Ethynyl-5-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 87394-65-8 , The common heterocyclic compound, 87394-65-8, name is 1-(5-Chloro-2-pyridyl)piperazine, molecular formula is C9H12ClN3, 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.

To a solution of triphosgene (300 mg) in CH2CI2 (5 mL) was added 1- phenylpiperidin-4-ol (352 mg, 1.99 mmol) over 3 hr, followed by the addition of a solution of 5-[(tert-butyldimethylsilyl)oxy]pyridin-2-amine (448 mg, 2.00 mmol, 1.00 eq) in pyridine (1 mL) over 16 hr. The resulting solution was stirred an additional 16 h at rt, then extracted with 2×30 mL of CH2CI2. The combined organic layers were concentrated under vacuum and purified with silica gel chromatography using CH2CI2 / MeOH (20: 1) to afford 270 mg (32%) of the title compound as an off-white solid. LC-MS: (ES, m/z) 428.

The synthetic route of 87394-65-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTAURUS THERAPEUTICS; ROMERO, Donna, L.; BLITZER, Jeremy; (242 pag.)WO2019/140188; (2019); 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. 13466-38-1, name is 5-Bromopyridin-2-ol. A new synthetic method of this compound is introduced below., Formula: C5H4BrNO

Synthesis of 5-bromo-2-(2-methoxyethoxy)pyridineTo a solution of 5-bromopyridin-2-ol (5.75 mmol, lg), triphenylphosphine (8.62mmol, 2.26 g), and 2-methoxyethanol (7.2 mmol, 0.55 g) in THF (25 mL), was added slowly diisopropyl azodicarboxylate (8.62 mmol, 1.7 mL) at RT. The mixture was stirred at RT overnight. The reaction was quenched with MeOH, diluted with water and extracted with DCM (25 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Crude was purified by flash chromatography (cyclohexane/EtOAc = 9/2 -> 7/3) to yield title product. Y: 1.05 g (79%), P>80%, rt=3.9 min (gradient A), (M+H)+ = 233.

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, 13466-38-1, 5-Bromopyridin-2-ol.

Reference:
Patent; EUROSCREEN S.A.; HOVEYDA, Hamid; DUTHEUIL, Guillaume; EL BOUSMAQUI, Mohamed; BERNARD, Jerome; WO2011/151434; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1150618-36-2, 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.1150618-36-2, name is 5-Bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H4BrF3N2, molecular weight is 265.03, as common compound, the synthetic route is as follows.

A mixture of 5-bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (0.250 g, 0.943 mmol), phenylmethanethiol (0.122 mL, 1.038 mmol), DIEA (0.329 mL, 1.887 mmol), Pd2(dba)3 (43.19 mg, 47.16 mumol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (54.58 mg, 94.33 mumol) in dioxane (10 mL) was stirred for 1 hour and heated to 150 C for 2 hours under microwave conditions. The mixture was cooled to RT and taken up in EtOAc. The organic layer was washed with NaHCO3(3x) and brine, dried (MgSO4), filtered and concentrated. The residue was purified via column chromatography (1:1EtOAc/hexane) to give the title compound as a yellow solid (0.78g, 95% yield). LCMS m/z = 309.4[M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1150618-36-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; TRAN, Thuy-Anh; ULLMAN, Brett; KRAMER, Bryan Aubrey; DO, Quyen-Quyen Thuy; SHIN, Young-Jun; (202 pag.)WO2019/113359; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 920979-04-0, 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, 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, Quality Control of 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, blongs to pyridine-derivatives compound. Quality Control of 2-Iodo-6-(trifluoromethyl)pyridin-3-amine

A solution of 2-iodo-6-(trifluoromethyl)pyri din-3 -amine (1.1 g, 3.82 mmol), triethylamine (1.60 mL, 11.5 mmol), palladium (II) acetate (231 mg, 1.03 mmol), tri(o- toly)lphosphine (86 g, 2.06 mmol), and methyl prop-2-enoate (1.6 g, 18.59 mmol, 5.00 equiv) in acetonitrile (100 mL) stirred overnight at 90 C in an oil bath. The resulting mixture was concentrated under vacuum. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate, and the combined organic phases were washed with 50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 :3 ethyl acetate/petroleum ether) to give methyl (2E)-3-[3-amino-6- (trifluoromethyl)pyridin-2-yl]prop-2-enoate (900 mg, 96%) as a yellow solid. MS: (ESI, m/z): 247[M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,920979-04-0, 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, the common compound, a new synthetic route is introduced below. Recommanded Product: 53937-02-3

To a solution of Compound 11 (1 g, 4.97 mmol) in DMF (10 mL) was slowly added sodium hydride (219 mg, 5.47 mmol) under ice-cooling, and the obtained reaction mixture was stirred under ice-cooling for 45 minutes. Methyl 2-bromopropionate was added dropwise thereto, and the obtained reaction mixture was warmed up to room temperature and then stirred overnight. To the reaction liquid was added water, followed by extraction with ethyl acetate. The organic layer was washed twice with water and then dried with magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The concentrated residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1 to 1:4) to obtain Compound 12 (1.03 g, 72%) as a yellow solid. Compound 12; 1H-NMR (CDCl3) delta: 1.62 (3H, d, J=7.60 Hz), 3.75 (3H, s), 4.99 (2H, s), 5.54 (1H, q, J=7.44 Hz), 5.99 (1H, d, J=2.53 Hz), 6.04 (1H, dd, J=7.60, 2.53 Hz), 7.19 (1H, d, J=7.60 Hz), 7.35-7.40 (5H, m).

The synthetic route of 53937-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; Kojima, Eiichi; Tonogaki, Keisuke; Tanaka, Nobuyuki; Katou, Manabu; Ino, Akira; Iwatsu, Masafumi; Fujioka, Masahiko; Hinata, Yu; Ohyabu, Naoki; (119 pag.)US9567330; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 499-51-4, 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. 499-51-4, name is 4-Hydroxypyridine-2,6-dicarboxylic acid. A new synthetic method of this compound is introduced below.

15 g of monohydric chelidamic acid (0.075 mol, I eq.) are dissolved in 120 mE of thionyl chloride under argon. The suspension is cooled to 00 C. and 3 mE DMF are added. The reaction mixture is then stirred for 12 hours with reflux. Volatiles are evaporated afier several toluene additions to remove the last traces of SOd2. The resulting yellowish solid is then dissolved in methanol and the mixture is refluxed for 12 hours to complete the reaction. After evaporation of the solvent, the residue is taken up by dichloromethane and washed successively with a saturated solution of NaHCO3, water and brine. The organic phase is then dried on Na2SO4, filtered and evaporated. Pure compound 12 is obtained by recrystallization in methanol to obtain 8.3of white crystalline powdet (R=44%). ?H-NMR (300 MHz, CDC13) oe (ppm)=8.29 (s,2H), 4.03 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,499-51-4, its application will become more common.

Reference:
Patent; ECOLE NORMALE SUPERIEURE DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE CLAUDE BERNARD LYON I; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; MAURY, Oliver; GIRARD, Eric; ENGILBERGE, Sylvain; RIOBE, Francois; (76 pag.)US2018/362550; (2018); 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C12H11NO2

g) tert-Butyl 8-(4-benzyloxy)-2-oxopyridin-1(2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (0.12 g, 0.33 mmol), 4-benzyloxy pyridinone (65 mg, 0.33 mmol), and Cs2CO3 (0.12 g, 0.38 mmol) were suspended in DMSO (2.0 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar, and 8-hydroxyquinoline (14 mg, 0.098 mmol) and copper iodide (74 mg, 0.39 mmol) were added to the suspension. The evacuation/Ar flushing process was repeated twice more, and the reaction mixture was heated at 133 C. for 18 h under N2. The mixture was cooled, diluted with 5:1 MeOH/NH4OH (25 mL), and the resulting solution was stirred at ambient temperature for 30 min. The reaction was further diluted with CH2Cl2 (75 mL), and the resulting solution was filtered through silica gel. The filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2 and washed with H2O (1*25 mL) and brine (3*50 mL). The organic solution was dried over Na2SO4, filtered and concentrated to dryness. Flash chromatography (12 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 10 column volumes, increased to 50:50 over 20 column volumes and held for 5 column volumes) gave the title compound (88 mg, 54%) as a yellow foam: 1H NMR (500 MHz, CDCl3) delta 7.63-7.52 (m, 2H), 7.42-7.36 (m, 5H), 7.31 (d, J=7.5 Hz, 1H), 6.99 (d, J=7.0 Hz, 1H), 6.10-6.09 (m, 1H), 6.04-6.03 (m, 1H), 5.05 (s, 2H), 4.71-4.62 (m, 2H), 4.14-4.10 (m, 5H), 2.97-2.96 (m, 2H), 2.04-2.03 (m, 2H), 1.44-1.37 (m, 9H).

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, 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 29681-43-4, 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.29681-43-4, name is Methyl 4-methoxypyridine-2-carboxylate, molecular formula is C8H9NO3, molecular weight is 167.16, as common compound, the synthetic route is as follows.

b) Lithium aluminum hydride (16 ml of a 1.0 N solution in diethyl ether, 16 mmol) was added to a solution of methyl 4-methoxypicoline-2-carboxylate (2.70 g, 16 mmol) in diethyl ether (50 ml) at ambient temperature. The reaction was stirred for 1 hour, poured into an aqueous solution of Rochelle’s salt (250 ml) and the reaction mixture extracted with ethyl acetate (3*50 ml). Purification of the crude product by flash chromatography on silica gel, eluding with dichloromethane-ethyl acetate, yielded 2-(hydroxymethyl)-4-methoxypyridine (800 mg, 36% yield) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 29681-43-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AstraZeneca AB; US7081461; (2006); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem