Pyridine-derivatives

Related Products of 78607-36-0 ,Some common heterocyclic compound, 78607-36-0, molecular formula is C5H3ClIN, 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.

EXAMPLE 31K 3-(4-tert-butylphenyl)-1-({2-[(2-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione To a solution of 0.8 g of 1-[(2-aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochloride obtained in stage c) of Example 7 in 50 mL of dioxane are successively added under argon 0.628 g of 2-chloro-3-iodopyridine, 2.8 g of caesium carbonate, 150 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (xantphos) and 49 mg of palladium diacetate. The reaction mixture is heated at 90 C. for 3 hours and then filtered, and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluding with a mixture of cyclohexane and ethyl acetate (70/30 by volume) to give 0.51 g of 3-(4-tert-butylphenyl)-1-({2-[(2-chloropyridin-3-yl)amino]pyridin-4-yl}methyl)-5,5-dimethylimidazolidine-2,4-dione, the characteristics of which are as follows: 1H NMR spectrum at 400 MHz: 1.31 (s, 9H); 1.43 (s, 6H); 4.57 (s, 2H); 6.89 (dd, J=1.5 and 5.5 Hz, 1H); 7.11 (broad s, 1H); 7.39 (m, 3H); 7.52 (d, J=8.5 Hz, 2H); 8.00 (dd, J=2.0 and 5.0 Hz, 1H); 8.10 (d, J=5.5 Hz, 1H); 8.55 (m, 2H). Mass Spectrum (ES): m/z=478 [M+H]+; m/z=476 [M-H]-

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. 78607-36-0, 2-Chloro-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2009/82379; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 110860-92-9, 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. 110860-92-9, name is 5,6-Dichloropyridin-3-ol. A new synthetic method of this compound is introduced below.

Sodium acetate (4.Og, 49.38mmoI) was added to a mixture of 5,6-dichloropyridin-3-ol (8g, 49.38mmol), Pd(OAc)2 (1.43g, 6.41 mmol) and Pd(dppf)C12 DCM complex (5.23g, 6.4lmmol) in EtOH (lOOmL) in an autoclave. The autoclave was filled with CO gas (22Opsi) and stirred at 90C for 6 h. The reaction mass was cooled to RT, excess gas evacuated in vacuo and the reaction mass was filtered through a celite bed. It was washed with EtOAc and the clear filtrate was concentrated under reduced pressure. Theresidue was purified by CC (0-40% EtOAc in PE) and the pure fractions were concentrated to get ethyl 3- chloro-5-hydroxypicolinate (9.2g, 93%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,110860-92-9, 5,6-Dichloropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (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.153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Chloro-4-iodopyridine

Intermediate 1; 4-Iodo-1H-pyridin-2-one; To 10.0 g (41.8 mmol) 2-chloro-4-iodopyridine in 100 mL AcOH are added 17.1 g (208 mmol) NaOAc and the reaction mixture is heated at 180 C. for 2 h in a microwave oven. DCM and water are added to the reaction mixture and the layers are separated. The organic layer is washed with water, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is triturated with TBME.C5H4INO (M=221.0 g/mol),ESI-MS: 222 [M+H]+ Rf (TLC): 0.3 (silica gel DCM/MeOH 9/1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214785; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53937-02-3, Adding some certain compound to certain chemical reactions, such as: 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone,molecular formula is C12H11NO2, 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 53937-02-3.

b) 4-(Benzyloxy)-1-(1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-8-yl)pyridin-2(1H)-one hydrochloride A suspension of 4-(benzyloxy)pyridin-2(1H)-one (71 mg, 0.35 mmol), tert-butyl 8-bromo-6-tosyl-1,2,4,5-tetrahydroazepino[4,5-b]indole-3(6H)-carboxylate (202 mg, 0.389 mmol), CuI (81 mg, 0.43 mmol), 8-hydroxyquinoline (62 mg, 0.43 mmol) and Cs2CO3 (127 mg, 0.389 mmol) in DMSO (10 mL) was degassed under reduced pressure for 45 min. The suspension was put under N2 and stirred at 135 C. for 4.5 h. The suspension was cooled, 9:0.9:0.1 CH2Cl2/MeOH/NH4OH (10 mL) was added, and the resulting suspension was stirred at 25 C. for 30 min. The suspension was passed through a plug of silica gel, and the filtrate was washed with brine. The resulting solution was dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded 190 mg of a yellow solid. NaOH (594 mg, 14.8 mmol) was added to a solution of the yellow solid in 1:1 MeOH/CH2Cl2 (20 mL) under N2, and the resulting suspension was stirred at reflux for 16 h. The reaction was cooled, H2O was added, and the resulting suspension was filtered. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) afforded a green solid. Preparative HPLC (Phenomenex Luna C18 (2), 250.0*50.0 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) afforded 50 mg of a white powder. 2 N HCl in Et2O (200 mL) was added to a solution of the white powder in 1:1 CH2Cl2/MeOH (4 mL) under N2, and the resulting suspension was stirred at 25 C. for 18 h. The suspension was filtered, and the solid was washed with Et2O to afford the title compound (35 mg, 23%) as a white solid: mp 258-260 C.; 1H NMR (500 MHz, DMSO-d6) delta 11.18 (s, 1H), 9.06 (br s, 2H), 7.57-7.35 (m, 7H), 7.25 (s, 1H), 6.90 (d, J=8.0 Hz), 6.11-6.07 (m, 1H), 5.96 (s, 1H), 5.15 (s, 2H), 3.45-3.30 (m, 4H), 3.20-3.15 (m, 2H), 3.12-3.06 (m, 2H); ESI MS m/z 386 [M+H]+.

According to the analysis of related databases, 53937-02-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); 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. 39919-65-8, name is 2,5-Dibromo-6-methylpyridine, molecular formula is C6H5Br2N, 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. name: 2,5-Dibromo-6-methylpyridine

Add to the reaction flask3,6-dibromo-2-methylpyridine (1.0 g, 3.9 mmol)And anhydrous ether (10 mL) were cooled to -78C,N-BuLi (1.6 M in hexanes, 2.4 mL, 3.9 mmol) was added dropwise,After stirring for 1 hour, anhydrous DMF (307 mg, 4.2 mmol) was added,The reaction was stirred at room temperature for 1 hour. Saturated ammonium chloride solution (10 mL) was added,Ethyl acetate (20 mL x 3). Combine organic phase,Saturated sodium chloride solution (20mL), dried over anhydrous sodium sulfate, suction filtration,Concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / petroleum ether = 1: 10)The resulting residue was purified to give the title compound (0.4 g, white solid) in 51% yield.

With the rapid development of chemical substances, we look forward to future research findings about 39919-65-8.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1214334-70-9, 5-Bromo-6-methoxypicolinic acid, 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, Computed Properties of C7H6BrNO3, blongs to pyridine-derivatives compound. Computed Properties of C7H6BrNO3

A solution of 5-bromo-6-methoxypicolinic acid (1.08 g, 4.45 mmol, 1.05 equiv.) in DCM (40.0 mL) at ambient temperature was treated with a catalytic amount of DMF (4 drops) and oxalyl chloride (1.17 mL, 13.4 mmol, 3.0 equiv.). The resultant mixture was stirred at ambient temperature for 1 h at which point LCMS monitoring showed completion of the reaction. The mixture was concentrated, diluted with anhydrous THF (20.0 mL), concentrated again and dried under high vacuum for 1 hour. The residue was diluted in anhydrous THF (20.0 ml), treated with triethylamine (1.86 mL, 13.4 mmol, 3.0 equiv.) and cooled to 0 C. A solution of (R)-2-(benzofuran-2-yl)-2-(4- methoxybenzylamino)ethanol (1.32 g, 4.45 mmol, 1.0 equiv.) in THF (20.0 ml) was quickly added and the resultant mixture was stirred at 0 C for 30 minutes. A saturated aqueous solution of NaHCO3 and EtOAc were then successively added. The layers were separated,and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography on silica (0-40% EtOAc / hexanes) to afford amide as white foam (1.78 g, 78%). LCMS (ES+) [M+Hj+: 511.2/513.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17282-40-5, 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 17282-40-5 as follows.

General procedure: Mixture of ethyl acetoacetate(1, 211 mg, 0.153 mmol), hydrazine (2, 81 mg, 0.153), 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde (4a, 406 mg,0.153 mmol), 1-(2-ethoxy-2-oxoethyl)pyridinium ylide (4, 272mg, 0.153 mmol), 0.1 equivalents of trimethylamine (16 mg,0.015 mmol) in15 mL EtOH were refluxed in a pre-heated oilbath (80 C) under the blanket of nitrogen for 30 min till the completion of reaction (TLC, 20 % dicholromethane in hexanes; Rf = 0.3). The reaction mixture was diluted with dichloromethane (10 mL) and the organic solution was washed with water (20 mL) and brine (20 mL) and dried over anhydrousNa2SO4. Column chromatographic purification on silica gelwith increasing amount of dichlormethane in hexanes provided 8a as a free flowing solid in about 88 % yield. Analytical samples were obtained through from the recrystallization in EtOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-40-5, its application will become more common.

Reference:
Article; Tangeti, Venkata Swamy; Vasundhara; Satyanarayana; Pavan Kumar, Kaja Srinivas; Asian Journal of Chemistry; vol. 29; 7; (2017); p. 1525 – 1532;,
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. 1427-06-1, name is Methyl 6-fluoropyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 6-fluoropyridine-3-carboxylate

( (2S) -5- (4- (trifluoromethyl) phenyl) piperidin-2-yl) methanol (294 mg, 1.13 mmol) , methyl 6-fluoropyridine-3-carboxylate (198 mg, 1.28 mmol) and K 2CO 3 (489 mg, 3.54 mmol) were dissolved in DMSO (3 mL) . The mixture was stirred for 24 h at an oil-bath temperature of 50 . The reaction mixture was cooled to room temperature, and to the mixture was added saturated NaCl solution (50 mL) , and the mixture was extracted with EtOAc (40 mL×2) . The combined organic layers were dried over anhydrous Na 2SO 4, and concentrated in vacuo to give a crude product, which was purified by silica-gel column chromatography (eluent: PET/EtOAc (v/v) = 5: 1) to give colorless oil (166 mg, 37%) . [2165] MS (ESI, pos. ion) m/z = 395.3 [M+1] +.

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, 1427-06-1, Methyl 6-fluoropyridine-3-carboxylate.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHONG, Xue; WANG, Feng; LI, Xuke; HE, Wei; PAN, Wei; HUANG, Jiuzhong; ZHANG, Yingjun; ZHENG, Changchun; (0 pag.)WO2020/11147; (2020); 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Quality Control of 5-Methylpyridin-2(1H)-one

General procedure: The coupling reaction was performed as follows: in a typical process, 5-methyl-2-(1H)-pyridone(1 mmol), aryl halide (1 mmol), base (2 mmol) and solvent (5 mL) were added to an oven-dried tube containing 5% (based on copper) MOF catalyst or copper salt. The mixture was stirred at desired temperature for 2 h. After being cooled to room temperature, the catalyst was filtrated and washed with ethyl acetate. The products were isolated by a series 1500 preparative high performance liquid chromatography system (SSI, Charlotte, NC, USA) equipped with a UV-VIS detector, using a Kromasil C18 column (50 x 250 mm) and gradient elution with a H2O (A)-acetonitrile (B) the mobile phase. The gradient program was 0 min, 10% B; 20 min, 35% B. The flow rate of mobile phase was 40 mL/min, and the detection wavelength was 220 nm. Fractions were collected and evaporated to afford the pure products.

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Article; Long, Wei; Qiu, Wenge; Guo, Chongwei; Li, Chuanqiang; Song, Liyun; Bai, Guangmei; Zhang, Guizhen; He, Hong; Kuznetsov, Maxim L.; Molecules; vol. 20; 12; (2015); p. 21178 – 21192;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56187-37-2, 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. 56187-37-2, name is 2-(3,5-Dichloro-4-oxopyridin-1(4H)-yl)acetic acid. A new synthetic method of this compound is introduced below.

In a dry reaction flask, 137.66 g of 3,5-dichloro-4-pyridone-1-acetic acid (0.62 mol) and 222.64 gDibenzothiazyl disulfide (DM, 0.6696 mol) was dissolved in 500 mL of dichloromethane and 54 g (0.682 mol) of pyridine was added.The reaction was stirred at room temperature for 1 hour, and then an aqueous solution of triethyl phosphite (118.47 g of triethyl phosphite dissolved in 150 mL of methylene chloride, 0.713 mol) was added dropwise slowly.1-2 hours dropwise addition is complete, the reaction temperature was controlled at 20-25 C for 1-2 hours, filtered and the filtrate cooled down to below 10 C,Crystals were precipitated, suction filtered and dried to give 234.8 g of cefoxitin side chain acid active ester (0.6063 mol). The yield was 97.1% and the HPLC purity was 99.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56187-37-2, 2-(3,5-Dichloro-4-oxopyridin-1(4H)-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Co., Ltd.; Wang Jun; Zuo Cuiyong; Gao Feifei; (10 pag.)CN105017286; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem