Category: pyridine-derivatives

Reference of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

Intermediate S-9 sodium 2-methoxy- -(trifluoromethyl)pyridine-4-thiolate Step a: To a -78 C solution of diisopropylamine (0.966 mL, 6.77 mmol) in THF (20 mL) was added ra-BuLi (1.6 M in hexanes, 4.23 mL, 6.77 mmol) dropwise and the reaction mixture was stirred for 5 min at -78 C. A solution of 2-methoxy-3- (trifluoromethyl)pyridine (1.2 g, 6.77 mmol) in THF (10 mL) was added and the resulting mixture was stirred for 2 h at -78 C. I2 (1.72 g, 6.77 mmol) in THF (5 mL) was added at -78 C and the resulting mixture was allowed to warm to RT within 30 min and was further stirred at this temperature for 30 min. The volatiles were removed under reduced pressure, the residue was dissolved in Et20 (200 mL) The organic layer was washed sequentially with sat. aq. Na2S2( (200 mL), sat. aq. NH4CI (200 mL), and sat. aq. NaHC03 (200 mL), dried over MgS04, filtered, and the volatiles were removed under reduced pressure. The residue was purified by silica chromatography (0 to 25% gradient of EtO Ac/heptane) to give 4-iodo-2-methoxy-3- (trifluoromethyl)pyridine (540 mg, 1.354 mmol). MS m/z, 304.0 (M+H)+.

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CHEN, Zhuoliang; FORTANET, Jorge Farcia; JOUK, Andriana; KARKI, Rajesh; LAMARCHE, Matthew J.; LIU, Gang; PALERMO, Mark G.; PEREZ, Lawrence Blas; SARVER, Patrick James; SHULTZ, Michael David; SENDZIK, Martin; TOURE, Bakary-Barry; YU, Bing; (173 pag.)WO2016/203406; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 139585-48-1, 2-Chloro-5-methoxypyridine, 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: 2-Chloro-5-methoxypyridine, blongs to pyridine-derivatives compound. name: 2-Chloro-5-methoxypyridine

5) 2-Hydrazino-5-methoxypyridine; A solution of the2-chloro-5-methoxypyridine (4.0 g) in hydrazine monohydrate (30 ml) was stirred at 100C for 24 hours. After cooling with air, the reaction solvent was evaporated under reduced pressure. To the residue was added chloroform and 1N aqueous sodium hydroxide and the phases were separated. The organic layer was dried over anhydrous magnesium sulfate. After filtration,_the solvent was evaporated under reduced pressure to give 2-hydrazino-5-methoxypyridine (705 mg, 18%) as an oily product. LC-MSm/z: 140 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139585-48-1, 2-Chloro-5-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1698626; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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, Recommanded Product: tert-Butyl (2-methoxypyridin-3-yl)carbamate, blongs to pyridine-derivatives compound. Recommanded Product: tert-Butyl (2-methoxypyridin-3-yl)carbamate

49. Preparation of t-Butyl N-(4-Fluoro-2-methoxy-3-pyridinyl)carbamate To a solution of 8 g (35.7 mmol) of t-butyl N-(2-methoxy-3-pyridyl)carbamate in 200 mL of dry tetrahydrofuran was added with stirring at -60 C., 46.2 mL (78.5 mmol) of 1.7M t-butyl lithium in pentane. The resulting solution was allowed to warm slowly with stirring to -20 C. over a 20 to 30 min period. It was then cooled to about -60 C. and 12.2 g (38.7 mmol) of N-fluorodibenzenesulfonimide was added with stirring all at once. The mixture was allowed to warm to -20 C. and was poured into 500 mL of ether. The resulting ethereal solution was washed with a mixture of 2.5 g (41.7 mmol) of acetic acid and 150 mL of water. The aqueous phase was extracted with 200 mL of ether. The ethereal extracts were combined, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by flash chromatography to obtain 6.7 g (77 percent of theory) of the title compound as a colorless solid melting at 75-77 C. Elemental Analysis C11 H15 FN2 O3 Calc.: %C, 54.5; %H, 6.24; %N, 11.6 Found: %C, 54.2; %H, 6.39; %N, 11.4 1 H NMR (CDCl3): 7.88 (dd, 1H, j=5.8, 7.6); 6.68 (dd, 1H, j=5.8, 8.9); 5.9 (br, 1H); 3.9 (s, 3H); 1.45 (s, 9H).

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DowElanco; US5571775; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1, 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.1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, molecular formula is C7H5BrFNO, molecular weight is 218.02, as common compound, the synthetic route is as follows.

Step 4. (R,E)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide To a solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (10.93 g, 50.1 mmol) in THF (100 ml) was added (R)-(+)-2-methyl-2-propanesulfinamide (12.15 g, 100 mmol) and titanium (IV)-ethoxide (20.75 mL, 100 mmol). The resulting mixture was then heated at reflux for 1 h. The mixture was cooled to RT and brine (300 mL) was added. The mixture was stirred at RT for 15 min, then filtered and the solid was washed with DCM (2*100 mL). The organic layer was collected and the aqueous layer was dried over MgSO4 and concentrated. The residue was then dissolved in DCM (10 mL) and purified by silica gel chromatography, eluent 0%-100% EtOAc/hexane, to give 14.9 g of the title compound as a yellow solid. MS (ESI, positive ion) m/z: 321, 323 (M+H).

Statistics shows that 1111637-74-1 is playing an increasingly important role. we look forward to future research findings about 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1187830-47-2, 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.1187830-47-2, name is 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine hydrochloride, molecular formula is C6H10ClN3, molecular weight is 159.62, as common compound, the synthetic route is as follows.

a) 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine.HCl (319 mg, 2 mmol) was combined with Boc2O (480 mg, 2.2 mmol) and K2CO3 (1.3 mL, 3 M aqueous, 2 equiv) in CH2Cl2 (10 mL). After 15 hours, the starting amine was consumed (LCMS). The reaction slurry was washed with brine and the organic layer was dried on MgSO4, filtered, and concentrated to give a viscous yellow oil (446 mg, 96%) that was used without further purification. MS: (ES) m/z calculated for C11H18N3O2 [M+H]+ 224.1, found 224.2.

Statistics shows that 1187830-47-2 is playing an increasingly important role. we look forward to future research findings about 4,5,6,7-Tetrahydro-2H-pyrazolo[4,3-b]pyridine hydrochloride.

Reference:
Patent; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 716362-10-6, 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 716362-10-6, name is 6-Chloro-4-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 6-chloro-N,4-dimethoxy-N-methylnicotinamide (3) (0673) To a solution of 6-chloro-4-methoxynicotinic acid (1, 25.0 g, 133.6 mmol) in dichloromethane (300 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38.44 g, 200.5 mmol), 1-hydroxybenzotriazole (30.40 g, 200.4 mmol) and N,N-diisopropylethylamine (69.8 mL, 400.8 mmol) were added at 0 C. and stirred the mixture for 5 min. N, O-dimethylhydroxylamine hydrochloride (2, 19.56 g, 200.53 mmol) was then added at same temperature and the reaction was stirred for 16 h at room temperature. After completion, reaction mass was diluted with dichloromethane and washed with cold water. The organic layer was separated and dried over sodium sulphate, filtered and concentrated to give crude. The crude was re-crystallised in ethanol to afford 6-chloro-N,4-dimethoxy-N-methylnicotinamide (3) as white solid. Yield: 19.3 g, 62%; MS (ESI) m/z 231.17 [M+1]+.

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 716362-10-6, 6-Chloro-4-methoxynicotinic acid.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; ERNST, Justin T.; REICH, Siegfried H.; SPRENGELER, Paul A.; TRAN, Chinh Viet; PACKARD, Garrick Kenneth; XIANG, Alan X.; NILEWSKI, Christian; MICHELS, Theo; (478 pag.)US2017/145026; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 898746-42-4 ,Some common heterocyclic compound, 898746-42-4, molecular formula is C7H5FN2, 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 6-fluoro-1H-pyrrolo[2,3-b]pyridine (2.50 g, 18.36 mmol) in DMF (50 mL) was added a solution of bromine (3.20 g, 20.00 mmol) in DMF (20 mL) at 0 C . After the addition, the mixture was stirred at rt for 2 h. To the mixture was added water (100 mL), then there was a lot of solid precipitated out. The mixture was filtered under reduced pressure, and the filter cake was washed with water (30 mL) for two times and then dried in vacuo at 60 C for 24 h to give the title compound as a white solid (3.44 g, 87%).MS (ESI, pos. ion) m/z: 217.1 [M+H]+1H NMR (400 MHz, DMSO-d6) (ppm): 12.20 (s, 1H), 8.04 – 7.95 (m, 1H), 7.67 (d, J = 2.5 Hz, 1H), 6.94 (t, J = 9.7 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,898746-42-4, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60010-03-9, 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloro-4-methyl-3-nitropyridine (6.5g; 31 .4 mmol) and TEA (10g; 3eq) in acetonitrile (200ml) was added (R)-(-)-3-fluoropyrrolidine hydrochloride (4.75g; 1 .2eq). The mixture was stirred for 4h at rt, after which the reaction mixture was quenched with sat NaHCOs(aq) (300ml), diluted with water and and EtOAc. The layers were separeted and the waterlayer was extracted with EtOAc (3x150ml_) untill no UV(254nm) active material was extracted). The combined organic layers were washed with brine and dried over Na2SO4(s). Filtration and in vacuo concentration resulted in a quantitative yield 8.36g of the title compound as a yellow/orange oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; STRØBAeK, Dorte; WO2011/26890; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 54221-93-1, 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 54221-93-1, name is 2,6-Dimethylisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

4-???2,6-????????????(3)2g?2,6-??????????(2)(??)?100ml?????????1ml?98%??24????????????????NaHCO3???????????60ml?CHCl3?5??????????????????????Na2SO4?????????????????????????50ml??????4????????????????????????????????????????????[?:???????/CH2Cl2(50/50)?CH2Cl2]????1g?4-???2,6-????????????(3)????

According to the analysis of related databases, 54221-93-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CIS BIO INTERNATIONAL, CIS; JP2004/509075; (2004); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1133879-69-2, 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.1133879-69-2, name is 3-Fluoro-5-vinylpyridine, molecular formula is C7H6FN, molecular weight is 123.1277, as common compound, the synthetic route is as follows.

General procedure: A mixture of tetrahydrocarbazole 5a (0.17 g,1 mmol), 5fluoro3vinylpyridine (6) (0.12 g, 1 mmol), CsF(0.1 g), and hydroquinone (0.02 g) in DMSO (1.5 mL) was heated with stirring at 130-140 C for 4 h, DMSO was evaporatedin vacuo (3 Torr), the product was extracted from residue withdichloromethane. The solvent was evaporated and the residuewas subjected to chromatography on silica gel (60 mesh), eluentmethanol-chloroform = 1 : 5. The yield was 0.22 g (75%), m.p.65-67 C. Found (%): C, 77.63; H, 6.43; N, 9.64. C19H19FN2.Calculated (%): C, 77.52; H, 6.45; N, 9.52. 1H NMR (DMSOd6), : 1.81 (m, 4 H, CH2); 2.29 (m, 2 H, CH2); 2.72 (m, 2 H,CH2); 3.05 (t, 2 H, CH2Py, J = 6.8 Hz); 4.25 (t, 2 H, CH2N,J = 6.9 Hz); 6.80 (dt, 1 H, CHPy, JHF = 9.3 Hz, JHH = 2.4 Hz);7.05-7.30 (m, 3 H, CHAr); 7.50 (d, 1 H, CHAr, J = 6.8 Hz); 8.14(s, 1 H, CHPy); 8.34 (d, 1 H, CHPy, JHH = 2.4 Hz). 19F NMR(DMSOd6), : -49.38 (d, JFH = 9.4 Hz).

Statistics shows that 1133879-69-2 is playing an increasingly important role. we look forward to future research findings about 3-Fluoro-5-vinylpyridine.

Reference:
Article; Sokolov; Aksinenko; Nikolaeva; Grigor’Ev; Kinzirsky; Bachurin; Russian Chemical Bulletin; vol. 63; 5; (2014); p. 1137 – 1141; Izv. Akad. Nauk, Ser. Khim.; 5; (2014); p. 1137 – 1141,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem