Tag: M.W:200-300

Application of 75806-86-9, 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 75806-86-9 as follows.

Example 3: General procedure A: Synthesis of 5-chloro-3-nitro-2-aryloxy- pyridines and 5-chloro-3-nitro-2-arylsulfanyl-pyridines; [00383] A mixture of the appropriate hydroxyaryl or thioaryl (1.3 equiv), 2- bromo-5-chloro-3-nitro-pyridine (1 equiv) and K2CO3 (1.5 equiv) in DMF was heated at 80 C overnight. The resulting mixture was cooled to room temperature, and diluted with water and CH2CI2. The biphasic mixture was separated and the aqueous portion was extracted with CH2CI2. The combined extracts were washed with saturated aqueous NaHCO3, brine and dried (Na2SO4). It was then filtered and filtrate was concentrated under reduced EPO pressure and the product was purified by flash column chromatography on silica gel to provide desired product.; Example 4: 5-Chloro-3-nitro-2-phenoxy-pyridine; [00384] This compound was prepared according to the general procedure described above using 2-bromo-5-chloro-3-nitro-pyridine (500 mg, 2.11 mmol), phenol (258 mg, 2.75 mmol), K2CO3 (437 mg, 3.16 mmol) and DMF (2 mL). MS m/z : 250.4 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75806-86-9, its application will become more common.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 942060-13-1, name is 3-(Bromomethyl)-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 942060-13-1

To a 100-mL round-bottomed flask were added 3-(bromomethyl)-2- methoxypyridine (1.10 g, 5.44 mmol), ethyl N-(diphenylmethylene) glycinate (1.46 g, 5.44 mmol, Acros, New Jersey) and 5N sodium hydroxide (5.44 mL, 27.2 mmol) in tetrahydrofuran (30 mL). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 50 mL). The organic extract was washed with saturated NaCl (20 mL) and dried over Na2S04. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give ethyl N-(diphenylmethylidene)-3-(2-methoxy-3- pyridinyl)alaninate (1.52 g) as viscous oil.

With the rapid development of chemical substances, we look forward to future research findings about 942060-13-1.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael David; BO, Yunxin; BRYAN, Marian C.; CROGHAN, Michael; FOTSCH, Christopher Harold; HALE, Clarence Henderson; KUNZ, Roxanne Kay; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis Dale; POON, Steve Fong; STEC, Markian Myroslaw; ST. JEAN, David, Joseph, Jr.; TAMAYO, Nuria A.; TEGLEY, Christopher Michael; YANG, Kevin Chao; WO2012/27261; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 436799-32-5, 5-Bromo-2-(trifluoromethyl)pyridine, 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: 5-Bromo-2-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. name: 5-Bromo-2-(trifluoromethyl)pyridine

In a dried 250 mL 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (16 mL, Aldrich, inhibitor free) followed by N, N-diisopropylamine (0.895 g, 8.85 mmol, Aldrich, redistilled 99.95% pure). After cooling the stirred solution to -70 0C, n-butyl lithium (3.54 mL of a 2.5M solution in hexanes, 8.85 mmol) was added dropwise, keeping the reaction temperature less than -60 0C. The resulting solution was stirred at -70 0C for a further 10 min, then warmed to -20 0C, before immediately cooling to -90 0C. A solution of 5-bromo-2-(trifluoromethyl)pyridine (2 g, 8.85 mmol) in anhydrous THF (8 mL, Aldrich, inhibitor free) was added dropwise, keeping the reaction temperature less than -85 0C. The resulting orange solution was stirred at -90 0C for 40 min.In a separate dried 250 mL 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (5 mL, Aldrich, inhibitor free) followed by methyl iodide (5 mL, 80 mmol). The solution was cooled to -90 0C. To this was added (via cannula) the solution of the pre-formed lithiated pyridine, controlling the rate so as to keep the reaction temperature of the receiving flask less than -80 0C. The resulting dark solution was stirred at -90 0C for a further 15 min (LCMS indicated reaction complete). The reaction was quenched with sat aq. NH4CI solution (50 mL), then allowed to slowly warm to room temperature. Organics were extracted with EtOAc (2 x 50 mL), then the combined organic layers washed with water (50 mL), then brine (50 mL), separated, dried over MgSO4, and then filtered. Concentration in vacuo gave 1.68 g of a brown oil which was purified via short-path vacuum distillation (45-46 0C, ca. 5 mmHg) to give 5-bromo-4-methyl-2- (trifluoromethyl)pyridine 1-2 (0.289 g, 14%) as a yellow oil (>97% pure). MS (M + H)+: 241.8, tR = 2.458 min (method 1 ); 1H NMR (CDCI3) delta 8.74 (1 H, s), 7.56 (1 H, s), 2.50 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,436799-32-5, 5-Bromo-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124610; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1026796-81-5, 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 1026796-81-5 as follows.

To a solution of N-(4-bromopyridin-2-yl)acetamide (350 mg, 1.6 mmol) in DCM (20 mL) was added mCPBA (1.26 g, 7.3 mmol) at 0 C. The reaction mixture was allowed to stir at rt for 3 h. The reaction mixture was then diluted with water and saturated K2CO3 solution, and extracted with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The crude compound was purified by column chromatography to provide N-(4-bromo-1-oxidopyridin-2-yl)acetamide (340 mg, 90%). LCMS (FA): m/z=231.3 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1026796-81-5, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17117-17-8, 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 17117-17-8 as follows.

(4E)-N-Methyl-N-(tert-butoxycarbonyl)-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine Under a nitrogen atmosphere, a mixture of 5-ethoxy-3-bromopyridine (1.20 g, 5.94 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.18 g, 5.94 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.5 mL, 10.8 mmol), and anhydrous acetonitrile (3 mL) was stirred and heated under reflux at 80-85 C. for 28 h. The resulting mixture, containing beige solids, was cooled to ambient temperature, diluted with water (20 mL), and extracted with CHCl3 (3*20 mL). The combined light-yellow CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried producing a yellow oil (1.69 g). The crude product was purified by column chromatography on silica gel (100 g), eluding with ethyl acetate-hexane (1:1, v/v). Selected fractions containing the product (Rf 0.20) were combined, concentrated by rotary evaporation, and the residue was vacuum dried to give 0.67 g (35.2%) of a light-yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17117-17-8, its application will become more common.

Reference:
Patent; Caldwell, William S.; Dull, Gary M.; Bhatti, Balwinder S.; Hadimani, Srishailkumar B.; Park, Haeil; Wagner, Jared M.; Crooks, Peter A.; Lippiello, Patrick M.; Bencherif, Merouane; US2003/125345; (2003); 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. 175204-82-7, name is Methyl 4-(trifluoromethyl)nicotinate, molecular formula is C8H6F3NO2, 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. Quality Control of Methyl 4-(trifluoromethyl)nicotinate

REFERENCE EXAMPLE 46 Production of (4-trifluoromethylpyridin-3-yl)-methanol; A solution of 0.37 g (9.7 mmoles) of lithium aluminum hydride dissolved in 100 ml of THF was cooled to -50 C. Thereto was gradually added dropwise a solution of 2.0 g (9.8 mmoles) of methyl 4-trifluoromethylnicotinate dissolved in 30 ml of THF. The mixture was stirred at -50 C. for 3 hours to give rise to a reaction. After confirmation of the completion of the reaction, ethyl acetate was added, followed by stirring for a while. Water was added, followed by stirring for a while. The reaction mixture was filtered under vacuum. The filtrate was extracted with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 0.6 g (yield: 35.3%) of (4-trifluoromethylpyridin-3-yl)-methanol as a yellow oily substance. 1H-NMR [CDCl3/TMS, delta (ppm)]: 9.00 (1H,s), 8.73 (1H,d), 7.51 (1H,d), 4.95 (2H,s)

With the rapid development of chemical substances, we look forward to future research findings about 175204-82-7.

Reference:
Patent; Takahashi, Satoru; Ueno, Ryohei; Yamaji, Yoshihiro; Fujinami, Makoto; US2005/256004; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75073-11-9, 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.75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.

PREPARATION 3 Diethyl 2-{[(5-iodo-6-methyl-2-pyridinyl)amino]methylene}malonate A solution of 2-amino-5-iodo-6-picoline (Prep 2 4.48 g) and diethyl ethoxymethylenemalonate (4.25 mL) is heated at 95 C. for 1.5 h. The reaction is cooled to room temperature. Hexanes (20 mL) are added and the resulting solid is filtered, washed with a minimal amount of hexanes, and dried to give the desired enamine (6.45 g, 83%). Physical Characteristics are as follows: m.p. 138-139 C.; 1H NMR (300 MHz, DMSO-d6) delta 10.70, 8.96, 8.11, 7.03, 4.21, 4.14, 1.26, 1.24; IR (drift) 2989, 1686, 1641, 1603, 1568, 1548, 1421, 1373, 1363, 1333, 1272, 1251, 1232, 1211, 800 cm-1; MS (ESI) m/z 404.9 (M+H)+, 402.9 (M-H)-; Anal. Calcd for C14H17IN2O4: C, 41.60; H, 4.24; N, 6.93; Found: C, 41.68; H, 4.35; N, 6.83.

Statistics shows that 75073-11-9 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-6-methylpyridin-2-amine.

Reference:
Patent; Vaillancourt, Valerie A.; US2002/7066; (2002); 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.23056-46-4, name is 2-Bromo-5-methyl-3-nitropyridine, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.Product Details of 23056-46-4

[00259] A round bottom flask was charged with 2-bromo-5-methyl-3- nitropyridine (60.53 g, 278.9 mmol) and CuCN (27.52 g, 307.3 mmol) The flask was evacuated, and back-filled with nitrogen. DMF (150 mL) was added via cannula. The solution was heated to 70 0C for 1.5 hours. After cooling to room temperature, the reaction mixture was poured into EtOAc (500 mL) and water (250 mL). Both phases were filtered through a 1 cm bed of celite. The layers were separated, and the organic phase washed with water (2 * 100 mL) then with a solution of 1 :1 sat. aq. NH4CI / NH4OH (2 x 100 mL). The combined aqueous layers were extracted with EtOAc (2 * 200 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (36.1Og, 79% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23056-46-4, 2-Bromo-5-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1196152-34-7, 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 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

(S)-2-Hydroxy-2,4-dimethylpentanoic acid (3073 g; 21 mol; 1.00 eq.), 4-dimethylaminopyridine (128 g; 1 mol; 0.05 eq.) and dichloromethane (24.5 L) are placed in a 100 L reactor. The reaction mixture is cooled to about 0 C. Pyridine (3.75 L) and dichloromethane (6 L) are added while maintaining the temperature at 0-5 C. (0238) Trimethylchlorosilane (5.8 L; 46 mol; 2.20 eq.) is added while maintaining the temperature below 5 C. The reaction mixture is warmed to 20 C. and stirred for 4 hours 30 minutes at this temperature, and then cooled to 0 C. N,N-Dimethylformamide (55 ml; 0.71 mol; 0.03 eq.) is added while maintaining the temperature below 5 C., and oxalyl chloride (1622 ml; 18.9 mol; 0.90 eq.) is then added while maintaining the temperature below 5 C. The reaction mixture is stirred for 1 hour at this temperature and N,N-dimethylformamide (27.50 ml; 0.36 mol; 0.02 eq.) is then added. The reaction mixture is warmed to about 20 C. and stirred for 1 hour at this temperature. (0239) A solution of 2-bromo-4-amino-6-methoxypyridine (3543 g; 17.4 mol; 0.83 eq.) in a dichloromethane (27.3 L)/pyridine (1.9 L) mixture is added to the preceding solution while maintaining the temperature below 25 C. The reaction mixture is stirred for 30 minutes at this temperature. The reaction progress is monitored by TLC with 5% control. (0240) A solution of acetic acid (23 L; 41 mol; 1.95 eq.) in ethanol (19 L) is prepared in a new disposable container of suitable volume and then poured into the reaction mixture while maintaining the temperature below 25 C. The reaction medium is stirred overnight at about 20 C. The reaction progress is monitored by TLC. (0241) An aqueous solution of hydrochloric acid (2.4 L; 12.00 M; 28.77 mol; 0.78 V) in water (27 L) is prepared in a new disposable container of suitable volume and then poured into the reaction medium and stirred for 10 minutes. The aqueous phase is discarded and the organic phase is then washed with water (30 L). The aqueous phase is discarded and the organic phase is then washed again with a solution prepared from NaOH (1 177.29 g; 29.43 mol; 1.40 eq.) in water (30 L). The aqueous phase is discarded and the organic phase is then washed again with water (30 L). (0242) The aqueous phase is discarded. The organic phase is clarified on a filter packed with active charcoal (921 g) and the cake is then washed with dichloromethane (10 L). The filtrate is then placed in the reactor and concentrated at reflux, distillate (37 L). Cyclohexane (43 L) is added to the reactor, which is then refluxed until the head temperature reaches 75 C. (distilled volume 22.5 L). Cyclohexane (10 L) is added and the reactor is allowed to cool to 27 C. An (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide initiator (138 g; 0.42 mol; 0.02 eq.) is added to promote the crystallization. The reaction mixture is cooled to 20 C. and then filtered through a 25 mum filter gauze. (0243) The reactor and the filter are rinsed with cyclohexane (10 L). The solid is dried in an oven at 45 C. under vacuum to give (S)-N-(2-bromo-6-methoxypyrid-4-yl)-2-hydroxy-2,4-dimethylpentanamide (3.7 kg; 65%). (0244) 1H NMR (400 MHz, DMSO-d6): 10.0 (bs, 1H); 7.73 (s, 1H); 7.33 (s, 1H); 5.70 (bs, 1H); 3.80 (s, 3H); 1.79-1.67 (m, 2H); 1.49 (dd, J=13.6 & 5.2 Hz, 1H); 1.32 (s, 3H); 0.89 (d, J=6.4 Hz, 3H); 0.78 (d, J=6.4 Hz, 3H)

According to the analysis of related databases, 1196152-34-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Galderma Research & Development; BOITEAU, Jean-Guy; DAVER, Sebastien; RODEVILLE, Nicolas; (19 pag.)US2019/10124; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 945954-94-9, name is Methyl 6-bromo-3-methoxypicolinate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 945954-94-9

A solution of methyl 6-bromo-3-methoxypicolinate (3.0 g, 12.19 mmol) andLiOHH2O (1.4 g, 33.36 mmol) in 1,4-dioxane / H20 (15 mL / 15 mL) was stirred at RT overnight. The mixture was filtered and the filtrate was adjusted to pH = 3 by aqueous HC1 (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2504 andconcentrated to give the crude product of 6-bromo-3-methoxypicolinic acid (2.1 g, yield: 73 %)without further purification. ?H-NMR (CDC13, 400 MHz) 10.05 (br s, 1H), 7.70 (d, J = 8.8 Hz,1H), 7.40 (d, J = 8.8 Hz, 1H), 4.01 (s, 3H). MS (M+H): 232 / 234.

With the rapid development of chemical substances, we look forward to future research findings about 945954-94-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem