Pyridine-derivatives

Electric Literature of 130722-95-1, 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. 130722-95-1, name is 3-(Benzyloxy)-5-bromopyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 3-(benzyloxy)-5-bromopyridine (1 g, 3.7 mmol) in toluene (25 mL), were added tris(dibenzylideneacetone)dipalladium(0) (169 mg, 0.185 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (230 mg, 0.37 mmol) and sodium tert-butoxide (710 mg, 7.4) and the flask was purged with argon. Thiomorpholine 1,1-dioxide (766 mg, 5.68) was added to the mixture and heated to 80 oC for 14 hours. After the completion of the reaction (monitored by TLC) the solvent was removed under vacuum. Water was added (10 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified on silica gel (Biotage; eluting solvents DCM: MeOH 10/1 ratio) to obtain red oil (720 mg, 60% yield); 1H NMR (500 MHz, CDCl3) delta 7.96 (m, 2H), 7.41-7.34 (m, 5H), 6.75 (t, J = 2.2 Hz, 1H), 5.10 (s, 2H), 3.85 – 3.83 (m, 4H), 3.08 – 3.06 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130722-95-1, 3-(Benzyloxy)-5-bromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Lamani, Manjunath; Malamas, Michael S.; Farah, Shrouq I.; Shukla, Vidyanand G.; Almeida, Michael F.; Weerts, Catherine M.; Anderson, Joseph; Wood, JodiAnne T.; Farizatto, Karen L.G.; Bahr, Ben A.; Makriyannis, Alexandros; Bioorganic and Medicinal Chemistry; vol. 27; 23; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67515-76-8, 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 67515-76-8 as follows.

The substrate 2,4-dichloro-6-hydroxybenzaldehyde (84 mg, 0.44 mmol)Dissolved in 10mL of 1,2-dichloroethane,To the solution was added 5-amino-2-methoxycarbonylpyridine (67 mg, 0.44 mmol)And titanium tetraisopropoxide (250 mg, 0.88 mmol). The reaction solution was stirred under reflux for 4 hours.Cool to room temperature and add 1 drop of acetic acid and sodium cyanoborohydride (83 mg, 1.32 mmol).Continue to reflux and stir overnight. Quenched with water, extracted with dichloromethane, combined, dried,The crude compound 29A (200 mg) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67515-76-8, its application will become more common.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
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. 635712-99-1, name is 6-(Benzyloxy)nicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-(Benzyloxy)nicotinaldehyde

To a stirred suspension of potassium tert-butoxide (0.440 g, 1.7 equiv) in methylene chloride (25 mL) at-20C was added N-benzyloxycarbonyl-a- phosphonoglycine trimethyl ester (1.3 g, 1.7 equiv) in methylene chloride (5 mL). The resulting solution was stirred for 5 min and treated with the 6-benzyloxy- pyridine-3-carbaldehyde (0.49 g, 2.28 mmol) in methylene chloride (5 mL). The reaction was stirred at-20C for 1 h, allowed to gradually warm to [0C,] and poured into a separatory funnel containing water and diethyl ether. The reaction was extracted with diethyl ether (2x), washed with brine, dried over magnesium sulfate, and concentrated to give 0.98 g (quant. ) as an oil which was used without purification. Mass spec.: 419.32 [(MH)] [+.]

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, 635712-99-1, 6-(Benzyloxy)nicotinaldehyde.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/104236; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 101990-70-9, Adding some certain compound to certain chemical reactions, such as: 101990-70-9, name is 5-(Chloromethyl)-2-methoxypyridine,molecular formula is C7H8ClNO, 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 101990-70-9.

tert-Butyl (5S)-2-[(6-methoxypyridin-3-yl)methyl]-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate tert-Butyl (5S)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate (1.33 g, 5.55 mmol) was initially charged in acetonitrile (30 ml). Caesium carbonate (4.52 g, 13.9 mmol), 5-(chloromethyl)-2-methoxypyridine (963 mg, 6.11 mmol) and sodium iodide (5.00 mg, 0.03 mmol) were subsequently added. After stirring for 4 days, the reaction mixture was admixed at room temperature with water and ethyl acetate. The organic phase was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. The residue was purified via column chromatography (silica gel, eluent: cyclohexane/ethyl acetate gradient). The product-containing fractions were concentrated under reduced pressure, and 751 mg (37% of theory) of the title compound were obtained. LC-MS (Method 3): Rt=1.56 min; MS (ESIpos): m/z=361 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.385 (16.00), 2.048 (0.54), 2.058 (0.48), 2.525 (0.41), 3.825 (6.81), 4.424 (0.60), 4.791 (2.68), 6.785 (0.78), 6.807 (0.84), 7.574 (0.51), 7.580 (0.52), 7.595 (0.49), 7.602 (0.50), 8.074 (0.67), 8.080 (0.65).

According to the analysis of related databases, 101990-70-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BIBER, Nicole; BROCKSCHNIEDER, Damian; GERICKE, Kersten Matthias; KOeLLING, Florian; LUSTIG, Klemens; MEDING, Joerg; MEIER, Heinrich; NEUBAUER, Thomas; SCHAeFER, Martina; TIMMERMANN, Andreas; ZUBOV, Dmitry; TERJUNG, Carsten; LINDNER, Niels; BADOCK, Volker; MOOSMAYER, Dieter; MIYATAKE ONDOZABAL, Hideki; MOORE, Steven; SCHULZ, Alexander; (458 pag.)US2019/160048; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 88139-91-7, Adding some certain compound to certain chemical reactions, such as: 88139-91-7, name is 5-Bromo-2-hydroxymethylpyridine,molecular formula is C6H6BrNO, 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 88139-91-7.

NaH (0.525 g, 13.1 mmol, 60% in mineral oil) was added to a solution of alcohol 41 (1.872, 10.1 mmol) and 5-bromo-2-(chloromethyl)pyridine (58) (prepared by chlorination of (5-bromo-2-pyridinyl)methanol, as reported by van den Heuvel et al., 2004) (2.5 g, 12.1 mmol) in anhydrous DMF (40 rnL) at 5 0C. The resulting mixture was stirred at room temperature for 2 h and then quenched with water (300 mL). The precipitate was filtered off, washed with water and dried to give (6S)-6-[(5-bromo-2-pyridinyl)methoxy]-2-nitro-6,7- dihydro-5H-imidazo[2,l-6][l,3]oxazine (59) (3.087 g, 86%) as a light brown solid: mp 171-173 0C; 1H NMR [(CD3)2SO] delta 8.65 (dd, J= 2.3, 0.4 Hz, 1 H), 8.04 (dd, J = 8.4, 2.4 Hz, 1 H), 8.02 (s, 1 H), 7.35 (dd, J = 8.4, 0.4 Hz, 1 H), 4.72-4.66 (m, 3 H), 4.49 (br d, J= 12.0 Hz, 1 H), 4.35- 4.21 (m, 3 H). Anal. (Ci2HnBrN4O4) C, H, N. HPLC purity: 99.4%.

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. 88139-91-7, 5-Bromo-2-hydroxymethylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; DENNY, William, Alexander; THOMPSON, Andrew, M.; BLASER, Adrian; MA, Zhenkun; PALMER, Brian, Desmond; SUTHERLAND, Hamish, Scott; KMENTOVA, Iveta; WO2011/14774; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884494-37-5 ,Some common heterocyclic compound, 884494-37-5, molecular formula is C6H5BrFN, 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.

[00415] Intermediate 44A. Methyl l-(3-fluoro-4-methylpyridin-2-yl)-lH-imidazole-4- carboxylate: A suspension of methyl lH-imidazole-4-carboxylate (83 mg, 0.658 mmol), 2-bromo-3-fluoro-4-methylpyridine (200 mg, 1.053 mmol), copper (I) iodide (125 mg, 0.658 mmol) and potassium carbonate (546 mg, 3.95 mmol) in DMSO (2 mL) was heated at 120 for 90 min under microwave conditions. The reaction mixture was quenched with H20, and the solid was suspended in EtOAc and MeOH. The combined organic layer was concentrated in vacuo, yielding oily residue, which was purified by reverse phase HPLC to give the desired product (5 mg, 3%). MS(ESI) m/z: 236.1 (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. 884494-37-5, 2-Bromo-3-fluoro-4-picoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 164513-39-7, Adding some certain compound to certain chemical reactions, such as: 164513-39-7, name is 5-Bromo-2-methoxy-4-methylpyridine,molecular formula is C7H8BrNO, 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 164513-39-7.

2-Methoxy-4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan2-yl)-pyridineA mixture of 5-bromo-2-methoxy-4-methyl-pyridine (0.26 g, 1.29 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (0.36 g, 1.42 mmol), potassium acetate (0.39 g, 4.0 mmol), and palladium acetate (9.0 mg, 2.8 mol %) in dimethylformamide (5 mL) was heated at 90 C. for 3 hours. The reaction was allowed to cool to room temperature, filtered, filtrate concentrated to dryness to give the crude title compound which was used directly in the Suzuki coupling reaction.

According to the analysis of related databases, 164513-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 607373-83-1, 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 607373-83-1, name is 2-Chloro-4-methoxy-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-chloro-4-methoxy-5-nitropyridine (0.6 g, 3.19 mmol), thiophene-2-boronic acid (0.45 g, 3.5 mmol), [l,l ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.26 g, 0.32 mmol) and cesium carbonate (1.55 g, 4.8 mmol) in DMF (12 mL) were stirred and heated in a sealed tube at 90C for 18h. The reaction mixture was cooled to room temperature, filtered through Celite and washed through with DCM. The filtrate was washed with water, dried (hydrophobic frit) and concentrated in vacuo. The residue was purified by column chromatography using silica gel and eluting with EtOAc in hexane (0-30%) to give the desired compound.

According to the analysis of related databases, 607373-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; SCHMITT, Benoit Antoine; GENEY, Raphael Jean Joel; DOYLE, Kevin James; PEACH, Joanne; PALMER, Nicholas John; JONES, Graham Peter; HARDY, David; DUFFY, James Edward Stewart; WO2013/117645; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89-00-9, 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. 89-00-9, name is Pyridine-2,3-dicarboxylic acid, molecular formula is C7H5NO4, 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.

To the solution of pyridine-2,3-dicarboxylic acid (50 g, 300 mmol) in MeOH (300 mL) was added SOCl2 (44 mL, 600 mmol), and the mixture was refluxed overnight. Volatiles were removed under vacuum, sat. Na2CO3 was added, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and evaporated under vacuum to give dimethyl pyridine-2,3-dicarboxylate as a colorless oil. Yield 32 g, 54percent.

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 89-00-9, Pyridine-2,3-dicarboxylic acid.

Reference:
Patent; MICURX PHARMACEUTICALS, INC.; WO2008/108988; (2008); 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. 13534-90-2, name is 3,4-Dibromopyridine, molecular formula is C5H3Br2N, 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. Computed Properties of C5H3Br2N

Aniline (86 mg, 0.929 mmol, 1.1 equiv.) was added to a pressure tube that was charged with 3,4-dibromopyridine 1 (200 mg, 0.844 mmol, 1 equiv.), Pd(OAc)2 (9 mg, 42 mumol, 0.05 equiv.), PPh3 (22 mg, 84 mumol, 0.1 equiv.) and sodium tert-butoxide (243 mg, 2.53 mmol, 3 equiv.) under argon. The tube was backfilled with argon several times. The degassed anhydrous toluene (7 mL) was added under argon. The reaction mixture then heated at 110 C for 5 h. After cooling, the reaction mixture was diluted with dichloromethane (10 mL), and the resulting mixture was filtered through a pad of Celite, which was washed three times with dichloromethane (30 mL). The filtrate was concentrated in vacuo. The crude product was purified by flash chromatography (silica gel; hexane/ethyl acetate, 10:1) to yield 8a (151 mg, 72%) as a colorless oil; 1H NMR (500 MHz, Chloroform-d) delta 8.48 (s, 1H), 8.13 (d, J = 5.7 Hz, 1H), 7.44 – 7.37 (m, 2H), 7.28 – 7.19 (m, 3H), 6.91 (d, J = 5.7 Hz, 1H), 6.52 (s, 1H); 13C NMR (126 MHz, Chloroform-d) delta 151.54, 148.79, 148.11, 138.47, 129.76, 125.54, 123.44, 108.39, 107.78.

With the rapid development of chemical substances, we look forward to future research findings about 13534-90-2.

Reference:
Article; Hung, Tran Quang; Hieu, Do Trung; Van Tinh, Dinh; Do, Ha Nam; Nguyen Tien, Tuan Anh; Van Do, Dang; Son, Le Thanh; Tran, Ngoc Han; Van Tuyen, Nguyen; Tan, Vu Minh; Ehlers, Peter; Dang, Tuan Thanh; Langer, Peter; Tetrahedron; vol. 75; 40; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem