Tag: M.W:100-200

100-26-5 ,Some common heterocyclic compound, 100-26-5, molecular formula is C7H5NO4, 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.

Concentrated sulfuric acid (3.9 mL, 71.6 mmol) was added dropwise over 15 minutes to a stirred suspension of 2,5-pyridinedicarboxylic acid (3.0 g, 17.9 mol) in absolute ethanol (10 mL) and the resulting mixture heated to reflux for 18 hours. The solution was allowed to cool to room temperature and the solvents evaporated under reduced pressure. Saturated NaHCC>3 solution was added to the residue to adjust the pH to -8 then the aqueous phase was extracted with EtOAc (4 x 50 mL). The combined organic extracts were washed with brine (30 mL), dried (Na2S04) and evaporated under reduced pressure to leave the title compound (3.0 g, 75%) which was used without further purification.

According to the analysis of related databases, 100-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENTINEL ONCOLOGY LIMITED; BOYLE, Robert George; WALKER, David Winter; BOYCE, Richard Justin; (165 pag.)WO2018/197714; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16867-03-1, 2-Amino-3-hydroxypyridine, 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, 16867-03-1, blongs to pyridine-derivatives compound. 16867-03-1

Step-1 [0134] To a stirred solution of 2-amino 3-hydroxy pyridine 1 (2 g, 16.26 mmol) in THF (20 ml) was added CDI (2.63 g, 16.26 mmol) and the total reaction mass stirred at reflux temperature for 16 h. Reaction mass was cooled to room temperature, THF was distilled and the crude material was partitioned between water and ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under vacuum to afford the desired compound 2 (0.5 g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16867-03-1, its application will become more common.

Reference:
Patent; Rangarajan, Radha; Kumar, Rajinder; Prabhakar, BV; Chandrasekhar, P; Mallikarjuna, P; Banerjee, Ankita; US2014/249170; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

6419-36-9, 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. 6419-36-9, name is 2-(Pyridin-3-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

Example 1-Preparation of risedronic acid A mixture of (3-pyridyl) acetic acid hydrochloride (10 g 0.06 moles) and phosphorous acid (47 g, 0.58 moles) is slowly added with phosphorus oxychloride (28.8 g 0.19 moles). The fluid mixture is warmed up to 60-70C for 24 hours, then added with 60 ml water at the same temperature. The mixture is refluxed for 6 hours, added with 0.3 g charcoal and hot-filtered through celite. The clarified solution is added with 160 ml acetone. The resulting precipitate is filtered, suspended in 50 ml water, dissolved at pH 7.5 (+/-0.2) with 30% sodium hydroxide. The resulting solution is acidified to pH 0.8 (+/-0. 2) and the precipitate is filtered and dried under vacuum at 40-50C to constant weight. 9. 8 g pure risedronic acid is obtained (yield: 60%).

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. 6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYOGEN LIMITED; WO2005/63779; (2005); A2;,
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. 5446-92-4, name is 2-Methoxy-5-nitropyridine. A new synthetic method of this compound is introduced below., 5446-92-4

General procedure: A stirred mixture of nitroarene 1 (1 mmol), allyl sulfone 2 (1.1 mmol), MgCl2 (60 mg, 0.62 mmol), and bis-trimethylsilylacetamide (BSA, 0.51 g, 0.64 mL, 2.5 mmol) in HMPA (2 mL) was treated with DBU (0.76 g, 0.75 mL 5.0 mmol). Stirring was continued for 2 days. After completion (disappearing of the nitroarene, TLC control), the reaction mixture was poured into saturated aqueous NH4Cl and extracted with ethyl acetate (3¡Á25 mL). After drying with MgSO4 and removal of the solvent the crude product was chromatographed Colorless crystals; mp 173-176 C (hexane/ethyl acetate); 1H NMR (400 MHz, CDCl3) delta 1.50 (s, 9H), 2.40 (s, 3H), 3.96 (s, 3H), 7.06 (d, J=8.5 Hz, 1H), 7.26-7.29 (m, 2H), 7.98 (d, J=7.5 Hz, 2H), 8.16 (d, J=9.0 Hz, 1H), 8.51 (s, 1H); 13C NMR (100 MHz, CDCl3) delta 21.62, 30.13, 38.45, 54.69, 117.13, 120.36, 128.50, 129.18, 135.14, 138.14, 140.20, 142.27, 142.91, 144.23, 162.13, 167.12; numax (film from CH2Cl2) 2886, 1679, 1460, 1296, 1201, 1150, 1067, 984, 746 cm-1; EIMS (70 eV) m/z (% relative intensity): 355 (29), 307 (16), 306 (54), 305 (100), 292 (15), 291 (44), 275 (17), 264 (19), 249 (37), 138 (15), 91 (16); HRMS (EI) for C20H22N2O3S calcd 370.1351; found 370.1347.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5446-92-4, 2-Methoxy-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Article; Anczkiewicz, Karolina; Krolikiewicz, Magdalena; Wrobel, Zbigniew; Wojciechowski, Krzysztof; Tetrahedron; vol. 71; 23; (2015); p. 3924 – 3931;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-18-8 , The common heterocyclic compound, 5470-18-8, name is 2-Chloro-3-nitropyridine, molecular formula is C5H3ClN2O2, 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 3-nitro-2-chloropyridine (4.0 g, 25.2 mmol) in 15 mL 2-methoxyethanol was added methylamine (2.0 M in THF, 32 mL). The reactionwas stirred for 8 hr at 80 C in a sealed tube. After cooling to rt, the reaction mixture was evaporated to afford 15 quantitatively (3.6 g, 23.2 mmol). 1H NMR (500 MHz, CDCl3) delta 8.47 – 8.37 (m, 2H), 8.20 (s, 1H), 6.64 (dd, J = 8.3, 4.4 Hz, 1H), 3.17 (d, J = 4.8 Hz, 3H). 13C NMR (126 MHz, CDCl3) delta 156.0, 153.5, 135.4, 111.7, 28.4. HRMS (ESI+) m/z calcd for C6H8N3O2+ 154.0617, found 154.0610.

According to the analysis of related databases, 5470-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pollock, Julie A.; Kim, Sung Hoon; Katzenellenbogen, John A.; Tetrahedron Letters; vol. 56; 44; (2015); p. 6097 – 6099;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The common heterocyclic compound, 151213-42-2, name is (4aR,7aR)-Octahydro-1H-pyrrolo[3,4-b]pyridine, molecular formula is C7H14N2, 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. 151213-42-2

General procedure: A mixture of 6-chloro-4-cyclopropyl-7-fluoro-1-oxo-1,4-dihydronaphthalene-2-carboxylic acid 1a (1 g, 3.5 mmol) with N-ethylpiperazine 2c (0.6 g, 5.25mmol) was loaded in a small flask fitted with a micro condenser, placed in the microwave reactor and irradiated for 25 min at 150C under solvent free conditions. The reaction progress was monitored by TLC. Upon completion of the process, addition of hot absolute ethanol (10 mL) to the reaction mixture was followed by filtration. The filtrate was concentrated and stored at room temperature for precipitation. The solid was filtered off and recrystallized from absolute ethanol to give compound 3c.

The synthetic route of 151213-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirzaie; Lari; Vahedi; Hakimi; Russian Journal of General Chemistry; vol. 86; 12; (2016); p. 2865 – 2869; Zh. Obshch. Khim.; vol. 86; 12; (2016); p. 2865 – 2869,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some common heterocyclic compound, 626-55-1, molecular formula is C5H4BrN, 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.626-55-1

Stage 1Methylpyridin-3-ylamine An amount of 100.1 g (633 mmol) of 3-bromopyridine was stirred with 160 ml (1280 mmol) of 8M methylamine in ethanol, 4 g (27.5 mmol) of 8-hydroxyquinoline and 2.2 g (11.5 mmol) of copper(I) iodide in an autoclave at 120 for 16 hours. The mixture was filtered with suction over sand/silica gel and concentrated, aqueous citric acid and cyclohexane were added to the residue, the aqueous phase was saturated with sodium chloride, admixed with dilute aqueous sodium hydroxide solution to a pH of 10 and extracted 6 times with ethyl acetate, and the combined organic phases were dried over MgSO4 and evaporated. The residue was distilled in a bulb tube under a membrane pump vacuum.Yield: 46.8 g (63% of theory), 1H-NMR (CD3CN) 2.75 (s, 3H), 4.3 (br, 1H), 6.85 (m, 1H), 7.05 (m, 1H), 7.8 (m, 1H), 7.95 (m, 1H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 626-55-1.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/305124; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-63-3, 2-Chloro-6-methylpyridine, 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, 18368-63-3, blongs to pyridine-derivatives compound. 18368-63-3

1, 1-dimethylethyl (6-methyl-2-Dyridinyl)acetateTo a stirred solution of tert-butyl acetate (1.013 mL, 7.50 mmol), 2-chloro-6-methylpyridine (638 mg, 5 mmol), chloro(2-di-t-butylphosphino-2′,4′,6′-tri-/’-propyl-1 , 1 ‘-biphenyl)[2-(2- aminoethyl)phenyl]palladium(ll) (34.3 mg, 0.050 mmol) in Toluene (10 mL) at 0 C in a 100-mL round bottom flask under N2 was added a solution of LHMDS (1 M in toluene) (15.00 mL, 15.00 mmol) pre-cooled to 0 C. The reaction was stirred for 30 minutes. LCMS indicated the reaction was complete, so it was poured into ammonium chloride (aqueous, saturated) and water (1 :1 , 40 mL), and extracted with ethyl acetate (3 x 100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-25% EtOAc in hexanes) to afford 1 , 1 -dimethylethyl (6-methyl-2-pyridinyl)acetate (918 mg, 4.43 mmol, 89 % yield) as a yellow oil. LC-MS(ES) m/z = 208 [M+H]+. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1.41 (s, 9 H), 2.44 (s, 3 H), 3.68 (s, 1 H), 7.12 (t, J=7.33 Hz, 2 H), 7.64 (t, J=7.71 Hz, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 18368-63-3.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); 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.13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.13534-99-1

equipped with a mechanical stirring three 500mL flask, 30g2- amino-3-bromo-pyridine, 52.8 g as an associated boronic acid pinacol ester, 300mL1,4- dioxane, 4.2gPd (dppf)2Cl2, 59.3g of anhydrous potassium acetate, purged with nitrogen three times, heated to about 80 open overnight.TLC the reaction was complete, cooling, filtration, the filter cake washed twice with 30mL dichloromethane and the filtrate was concentrated to dryness, 200mL of methanol and 20g active carbon was stirred at room temperature overnight, filtration.Concentrated to dryness to give an oil, and petroleum ether was added 15mL 200mL MTBE heating overnight, filtered to give 28g2-amino-4-boronic acid pinacol ester in a yield of 72.8%.

Statistics shows that 13534-99-1 is playing an increasingly important role. we look forward to future research findings about 2-Amino-3-bromopyridine.

Reference:
Patent; Shanghai Rainbow Chemistry Co.,Ltd; Wu, Gang; Yan, taotao; Wei, xianli; (13 pag.)CN102786543; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

115473-15-9, Adding a certain compound to certain chemical reactions, such as: 115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, 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, 115473-15-9, blongs to pyridine-derivatives compound.

To a reaction flask equipped with a stirrer, a condenser and a thermometer was added 19.2 g of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one, which was then dispersed in 80 mL dichloromethane and cooled to 0 C. under stirring. 30.4 g of triethylamine were added to the mixture. After addition of 15.2 g of 3-cyanobenzyl bromide to the reaction system in batches, the reaction mixture was heated to reflux and continued to react for 5 h (completion of the reaction was monitored by TLC). The reaction liquid was washed with water (3¡Á80 mL). Then the dichloromethane layer was separated, fully dried over anhydrous sodium sulfate, and filtered. The dichloromethane was evaporated off under reduced pressure to obtain 20.8 g light yellow solid product (HPLC: 96.4%). Rf=0.45 [single point, developing solvent: v (petroleum ether): v (ethyl acetate)=1:2]. MS, m/Z: 270.0 (M).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115473-15-9, its application will become more common.

Reference:
Patent; TIANJIN INSTITUTE OF PHARMACEUTICAL RESEARCH; LIU, Dengke; LIU, Ying; YUE, Nan; CHEN, Furong; TAN, Chubing; ZHOU, Yunsong; LIU, Peng; ZHAO, Yigui; ZHI, Deguang; LIU, Mo; LIU, Bingni; HUANG, Changjiang; TANG, Lida; US2013/72521; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem