Tag: M.W:200-300

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. 670253-37-9, name is 4-Chloro-5-iodopyridin-2-amine. A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-5-iodopyridin-2-amine

In a one-neck round bottom flask, 90.7 g (357.1 mmol) of compound IF was added to 500 ml of NMP, and 21.4 g (182.1 mmol) of Zn(CN)2 was added, and 41 g (35.7 mmol) of Pd(PPh3)4 was quickly added, reacted at 135C for 5 h. After the reaction was completed, a brown oily liquid was given. The reaction mixture was slowly poured into 3 L of ice water under stirring, and a large amount of tan solid was precipitated, filtered, washed with water and dried to give compound 1G, ESI-MS m/z: 154.2 [M+H]+.

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, 670253-37-9, 4-Chloro-5-iodopyridin-2-amine.

Reference:
Patent; Shanghai Zheye Biotechnology Limited-Liability Company; LIU, Jianyu; ZHANG, Haidong; (30 pag.)EP3564242; (2019); 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. 849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 849068-61-7

Example 1; Methyl 5-bromo-l/7-pyrrolo [2,3-/>] pyridine-3-carboxylate; A solution of 5-bromo-l//-pyrrolo[2,3-6]pyridine (0.200 g, 1.01 mmol; described in: Mazeas,D. et al, Heterocycles 1999, 50, 1065-1080) in dichloromethane (12 mL) was added to asuspension of aluminum chloride (0.704 g, 5.28 mmol) in dichloromethane (5 mL) under anatmosphere of nitrogen. The resulting mixture was stirred at room temperature for 40 min togive a brownish solution. Trichloroacetyl chloride (0.56 mL, 5.0 mmol) was added and themixture was stirred at room temperature for 17 h. Methanol (10 mL) was added and thesolvent was evaporated in vacuo. The residue was treated with aqueous potassium hydroxide(3 M, 10 mL) and methanol (5 mL) and heated at 60 C for 1 h and 15 min. The mixture wasallowed to cool to room temperature and the pH was adjusted to 1-2 using aqueoushydrochloric acid (2 M). The aqueous phase was extracted with ethyl acetate, dried oversodium sulfate, and the solvent was evaporated to give a brown residue. Acetyl chloride (10mL) was added dropwise to cooled methanol (0 C, 20 mL). The resulting solution was addedto a solution of the brown residue in methanol (10 mL) at room temperature, and the resultingmixture was heated at reflux for 3 h. The mixture was allowed to cool to room temperatureand the solvent was evaporated to give a yellow solid. The crude product was purified on asilica gel column using a gradient, ethyl acetate/heptane mixture (10, 20, 30,40, 50% ethylacetate), as the eluent to give 0.165 g (64% yield) of the title compound as a pale pink solid:’H NMR (DMSO-d6, 300 MHz) 5 12.80 (br s, 1 H), 8.41 (s, 2 H), 8.30 (d, J= 3.0 Hz, 1 H),3.83 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) 6 163.9, 147.0, 144.1, 134.5,130.5, 119.6,113.1, 105.0, 51.1; MS (ES) m/z 255 and 257 (M++l).

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, 849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; WO2006/1754; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1026796-81-5, 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. 1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide. A new synthetic method of this compound is introduced below.

[00180] To a mixture of N-(4-bromopyridin-2-yl)acetamide (17.2 g, 80 mmol), 4,4,4,4,5,5,5,5?- octamethyl-2,2?-bi-1,3,2-dioxaborolane (26.4 g, 104 mmol), Pd(dppf)C12 (11.7 g, 16 mmol) and KOAc (23.6 g, 240 mmol) under an atmosphere of nitrogen was added anhydrous DMF (1500 mL). The mixture was allowed to stir at 80C for 3.5 h. The solvent was removed and the residue was diluted with EtOAc (1000 mL). Activated carbon (100 g) was added. The slurry was heated at reflux for 5 mm and then filtered. The organic solution was concentrated and the residue was recrystallized from EtOAc to give N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (6.1 g, 29%) as a white solid. 1H NEVER (400 JVEFIz, DMSO-ds): 6 1.29 (s, 12H), 2.09 (s, 3H), 7.24 (dd, J= 6.0, 1.2 Hz, 1H), 8.30-8.33 (m, 2H), 10.47 (br s, 1H).

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; WO2015/108861; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 132834-56-1, 1-(6-Chloro-5-(trifluoromethyl)pyridin-2-yl)piperazine, 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, 132834-56-1, blongs to pyridine-derivatives compound. Recommanded Product: 132834-56-1

4-(Thiophen-2-yl)butanoic acid (100 ??, 0.68 mmol), HOBt (1 10 mg, 0.816 mmol), TBTU (262 mg, 0.816 mmol), anhydrous triethylamine (152 ??, 1.08 mmol) and anhydrous DMF (2 mL) were placed in an oven-dried Schlenk tube under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 15 minutes. A second Schlenk tube was prepared containing 1-(6-chloro-5- (trifluoromethyl) pyridin-2-yl)piperazine (218 mg, 0.816 mmol) and anhydrous DMF (1 mL) under a nitrogen atmosphere. The resulting solution was stirred until complete dissolution of the piperazine had occurred. The piperazine solution was then transferred, via a cannula, to the first Schlenk tube containing the carboxylic acid. The resulting solution was stirred under nitrogen and monitored by TLC. After 24 hours, the DMF was removed under reduced pressure and the resulting oil was acidified using a 0.1 M HCI solution. The aqueous mixture was extracted with DCM (20 mL, followed by 4 x 10 mL) and the organic layer washed with a saturated sodium bicarbonate solution (3 x 20 mL) and brine (3 x 20 mL). The organic layer was dried over magnesium sulphate and the solvent removed in vacuo. The residue was purified using flash chromatography (3:2, EtOAc:n-hexane) to obtain the desired product in a 68% yield. H NMR (300 MHz, CDCI3) ? 7.66 (d, J = 8.7 Hz, 1 H), 7.10 (dd, J = 5.1 Hz, J = 1 .2 Hz, 1 H), 6.92-6.89 (m, 1 H), 6.80-3.79 (m, 1 H), 6.46 (d, J = 8.7 Hz, 1 H), 3.72- 3.67 (m, 4H), 3.97-3.57 (m, 2H), 3.52-3.49 (m, 2H), 2.88 (t, J = 7.5 Hz, 2H), 2.31 (t, J = 7.5 Hz, 2H), 2.09-1.99 (m, J = 7.2 Hz, 2H). 3C NMR (75 MHz, CDCI3) 171.2, 158.9, 147.5, 144.2, 137.6 (q, J = 3.75 Hz), 126.8, 124.5, 123.2, 1 17.8 (q, J = 268.5 Hz), 1 12.0 (q, J = 33 Hz), 103.3, 44.7, 44.5, 44.1 , 40.7, 31 .9, 29.2, 26.9. MS (+ESI) calcd for C18 H19 CI F3 N3 O S m/z: [M + H]+, 418.0962; found 418.0953 [Diff(ppm) = -2.23].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,132834-56-1, its application will become more common.

Reference:
Patent; NATIONAL UNIVERSITY OF IRELAND, MAYNOOTH; STEPHENS, John; FINDLAY, John; KINSELLA, Gemma; MARTIN, Darren; DEVINE, Robert; VELASCO-TORRIJOS, Trinidad; WO2013/60860; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Quality Control of 5-Bromo-N2-methylpyridine-2,3-diamine, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-N2-methylpyridine-2,3-diamine

To a suspension of 5-bromo-N2-methylpyridine-2,3-diamine (510 mg, 2.51 mmol) in AcOH (20 mL) was added MeC(OEt)3 (1 mL) and the solution was warmed to 80 C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The crude residue was purified by silica gel column chromatography (0-25% THF/CH2Cl2 gradient) to afford the desired product. 1H NMR (400 MHz, CDCl3) delta 8.36 (d, J=1.8 Hz, 1H), 8.06 (d, J=1.9 Hz, 1H), 3.80 (s, 3H), 2.65 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Babaoglu, Kerim; Brizgys, Gediminas; Cha, Jake; Chen, Xiaowu; Guo, Hongyan; Halcomb, Randall L.; Han, Xiaochun; Huang, Richard; Liu, Hongtao; McFadden, Ryan; Mitchell, Michael L.; Qi, Yingmei; Roethle, Paul A.; Xu, Lianhong; Yang, Hong; US2013/281433; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 889944-76-7, 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. 889944-76-7, name is 6-Chloro-4-methylpyridine-3-sulfonyl chloride. A new synthetic method of this compound is introduced below.

A mixture of 6-chioro-4-methyipyridine-3-sulfonyl chloride (0.25 g, 1.106 mmol) in THF (5 mL) was treated with Hunig’s Base (0.290 mL, 1.659 mmol), followed by dimethylamine (2.0 M in THF, 0.829 mL, 1.659 mmol) at room temperature. After 1 hour, the reaction was concentrated and the crude was purified by column chromatography (24g Si02, 0 to 100% EtO Ax-hexanes, gradient elution) to afford 6- chloro-N,N,4-trimethylpyridine-3-sulfonamide (213 mg, 0.908 mmol, 82 % yield). LCMS(M+H) = 234.9; LCMS RT = 0.79 min; (Column: BEH Cl 8 2.1 x 50mm; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: acetonitrile with 0.05% TFA; Temperature: 50 C; Gradient: 2-98% B over 1.7 min; Flow: 0.8 mL/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,889944-76-7, 6-Chloro-4-methylpyridine-3-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TARBY, Christine M.; NORRIS, Derek J.; LO, Julian C.; AHUJA, Vijay T.; SEITZ, Steven P.; GAVAI, Ashvinikumar V.; TOKARSKI, John S.; RAJASAGI, Mohini; WICHROSKI, Michael; BROEKEMA, Matthias; (155 pag.)WO2019/213340; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 195044-14-5, Adding some certain compound to certain chemical reactions, such as: 195044-14-5, name is 2-Bromo-6-tert-butylpyridine,molecular formula is C9H12BrN, 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 195044-14-5.

Step-1: Synthesis of 1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (400 mg, 1.78 mmol, 1.0 eq) and 2-bromo-6-(tert-butyl)pyridine (458 mg, 2.14 mmol, 1.20 eq) in (12 mL) of dioxane was added potassium carbonate (492 mg, 3.56 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 10 min followed by addition of copper iodide (68 mg, 0.356 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (63 mg, 0.712 mmol, 0.4 eq) and again purged with nitrogen for 10 min, stirred at 90 C. for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-30% EtOAc in hexane] to afford the desired product, 1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (366 mg, 57.40%) as colorless liquid. LCMS: 358.2 [M+1]+

According to the analysis of related databases, 195044-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); 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.623585-74-0, name is Methyl 2,5-dichloroisonicotinate, molecular formula is C7H5Cl2NO2, molecular weight is 206.03, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Two solutions of methyl 2,5-dichloroisonicotinate (623585-74-0, 894 mg, 4.34 mmol) in THF (18 mL) and dimethylzinc (2M in toluene, 5.3 mL, 10.6 mmol) in toluene (12.7 mL) were pumped using a syringe pump through a column containing SyliCat DPP- Pd (800 mg, 0.26 mmol/g) at 80 C, 0.1 mL/min (each), Rt= 5 min. The outlet solution was collected onto water and the solvent evaporated in vacuo. The crude was diluted with water and extracted with DCM and washed with water (3x). The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo to yield intermediate compound 1-107 (481 mg, 67%) as a colorless oil/solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,623585-74-0, Methyl 2,5-dichloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ALONSO-DE DIEGO, Sergio-Alvar; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; CONDE-CEIDE, Susana; ANDRES-GIL, Jose, Ignacio; DELGADO-GONZALEZ, Oscar; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; (211 pag.)WO2016/16395; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 886371-28-4, name is 3-Bromo-6-chloroimidazo[1,2-a]pyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C7H4BrClN2

General procedure: To an oven-dried 5 mL microwave vessel was addedPd(dppf)Cl2·CH2Cl2 (4 mol%), aryl halide/pseudohalide (1equiv.), organoboron (1 equiv.), and K3PO4 (3 equiv.). The vesselwas then capped and purged with N2 before addition of DMI (1mL, 0.25 M) and H2O (5 equiv.). The reaction mixture washeated to 60 C and maintained at this temperature with stirringfor 1 h before the vessel was vented and decapped. Thesolution was then diluted with EtOAc (10 mL) and washed withwater (2 × 20 mL) and brine (2 × 20 mL). The organics were thenpassed through a hydrophobic frit and concentrated underreduced pressure to give a residue, which was purified by flashchromatography (silica gel) to afford the product.

The synthetic route of 886371-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wilson, Kirsty L.; Murray, Jane; Sneddon, Helen F.; Jamieson, Craig; Watson, Allan J. B.; Synlett; vol. 29; 17; (2018); p. 2293 – 2297;,
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. 905273-87-2, name is 6-Chloro-N,N-diisopropylnicotinamide, molecular formula is C12H17ClN2O, 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. category: pyridine-derivatives

To a stirred solution of diisopropylamine (1 g, 9.88 mmol, 4.76 equiv) in ether (30 mL) at -50C maintained under nitrogen was added a 2.5 M solution of n-BuLi (5 mL) in hexanes dropwise The reaction mixture was stirred for 30 min a -50C then solid 6- chloro-N,N-bis(propan-2-yl)pyridine-3-carboxamide (500 mg, 2.08 mmol, 1.00 equiv) was added in a single portion. The resulting solution was stirred for 30 min at -50C DMF (1 mL) was then added dropwise with stirring. The reaction mixture was stirred at -50C for 3 h and then warmed to rt and stirred overnight. The reaction was quenched by the addition of 10% aqueous citric acid solution (30 mL) and then extracted with 2×50 mL of ether. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give 0.5 g of crude 6-chloro-4-formyl-N,N-bis(propan-2-yl)pyridine-3-carboxamide as a yellow solid. LC/MS (Method G, ESI): RT= 1.40 min, m/z = 269.0 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 905273-87-2.

Reference:
Patent; GENENTECH,INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Kanl H.; DRAGOVICH, Peter; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; YUEN, Po-Wai; ZAK, Mark; ZHANG, Yamin; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/127268; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem