Month: March 2022

Adding a certain compound to certain chemical reactions, such as: 29241-66-5, 5-Bromo-2-fluoronicotinic acid, 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, HPLC of Formula: C6H3BrFNO2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3BrFNO2

Iodomethane 0.75 mL (12 mmol) and potassium carbonate 2.5 g (18 mmol) were added to a DMF (8 mL) solution of 5-bromo-2-fluoronicotinic acid 2.0 g (9.1 mmol), and the mixture was stirred at room temperature for 20 hours. After the completion of the reaction, water was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (eluting solvent: hexane:ethyl acetate) to give the title compound 1.7 g (7.3 mmol, yield 80%) as a white solid. Mass spectrum (CI, m/z):234, 236[M+1]+. 1H-NMR spectrum (400MHz, DMSO-d6) delta:8.66 (dd, J = 1.3, 2.6 Hz, 1H), 8.56 (dd, J = 2.6, 8.2 Hz, 1H), 3.89 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29241-66-5, 5-Bromo-2-fluoronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; UBE Industries, Ltd.; KOMORI, Ken-ichi; NINOMIYA, Akishi; USHIYAMA, Shigeru; SHINOHARA, Masaru; ITO, Koji; KAWAGUCHI, Tetsuo; TOKUNAGA, Yasunori; KAWADA, Hiroyoshi; YAMADA, Haruka; SHIRAISHI, Yusuke; KOJIMA, Masahiro; ITO, Masaaki; KIMURA, Tomio; (432 pag.)EP3333163; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 799293-73-5, 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. 799293-73-5, name is 3-Bromofuro[3,2-c]pyridin-4-amine, molecular formula is C7H5BrN2O, 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.

1, 1-dimethylethyl 5-(4-aminofurof3,2-clDyridin-3-yl)-4-fluoro-2,3-dihvdro-1H-indole-1- carboxylate3-Bromofuro[3,2-c]pyridin-4-amine (310 mg, 1 .455 mmol), 1 , 1-dimethylethyl 4-fluoro-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-indole-1-carboxylate (577 mg, 1 .589 mmol), PdCI2(dppf)-CH2CI2 adduct (65 mg, 0.080 mmol), 1 ,4-Dioxane (15 mL), and saturated aqueous sodium bicarbonate (4.5 mL, 4.50 mmol) were added to a 200 mL flask equipped with a reflux condenser. The flask was evacuated and filled with nitrogen 4 times, and then the mixture was stirred at 100 C under Nitrogen for 15 hours. LCMS showed complete and clean conversion, so it was cooled and filtered through celite, rinsing with EtOAc (50 mL). The filtrate was washed with half-saturated aqueous NaHC03 (50 mL), and the aqueous phase was back-extracted with ethyl acetate (2 chi 50 mL). The combined organic phases were washed with brine (1 chi 100 mL), dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (Analogix, 60 g Si02, 10%-75% EtOAc in hexanes gradient over 60 minutes) to give 1 ,1 -dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-4-fluoro-2,3-dihydro- 1 H-indole-1 -carboxylate (205 mg, 0.555 mmol, 38.1 % yield) as an off-white solid. LC/MS (ES) m/z = 370 [M+H]+

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 799293-73-5, 3-Bromofuro[3,2-c]pyridin-4-amine.

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

Adding a certain compound to certain chemical reactions, such as: 912934-77-1, 6-Bromopyridine-2-sulfonyl chloride, 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: 6-Bromopyridine-2-sulfonyl chloride, blongs to pyridine-derivatives compound. name: 6-Bromopyridine-2-sulfonyl chloride

Step 1-Preparation of 1-((6-bromopyridin-2-yl)sulfonyl)pyrrolidine-3-carbonitrile, 64 To 6-bromopyridine-2-sulfonyl chloride (100 mg, 0.39 mmol) was added pyrrolidine-3-carbonitrile (37.48 mg, 0.39 mmol) and dichloromethane (2 ml). The reaction was allowed to stir at room temperature for 30 minutes. The reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to dryness to provide 1-((6-bromopyridin-2-yl)sulfonyl)pyrrolidine-3-carbonitrile 64. This material was used in the next step without further purification.

The synthetic route of 912934-77-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Plexxikon Inc.; Wu, Guoxian; Wu, Jeffrey; Chan, Katrina; Dong, Ken; Ewing, Todd; Ibrahim, Prabha N.; Lin, Jack; Spevak, Wayne; Zhang, Ying; (150 pag.)US2017/158690; (2017); 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. 1440519-73-2, name is 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one. A new synthetic method of this compound is introduced below., Recommanded Product: 1440519-73-2

General procedure: Procedure A: To a solution of 5-bromo-2-(4-methoxybenzyl)isoindolin-1-one (1, 0.5 g, 1.5 mmol) in dioxane (10 mL) was added 7H-pyrrolo[2,3-d]pyrimidine (2, 0.27 g, 2.25 mmol) and potassium tert-butoxide (0.51 g, 4.52 mmol) followed by the addition of XantPhos (0.087 g, 0.15 mmol). The reaction mixture was degassed with argon for 15 min. Tris(dibenzylideneacetone)dipalladium(0) (0.14 g, 0.15 mmol) was then added and the reaction mixture was heated at 90 C. and maintained at that temperature for 12 h. (0193) Following heating, the reaction mixture was cooled and concentrated under reduced pressure. The concentrated reaction mixture was extracted in ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel (100-200 mesh) column chromatography using 5% methanol in dichloromethane as eluent so as to afford 2-(4-methoxybenzyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one (3). Yield: 0.21 g, 38%;

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, 1440519-73-2, 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); 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 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H9N3O

General procedure: To a 1 dram vial was added 2-substituted-4-phenoxy intermediate 25 (0.066mmol), substituted aminopyridine (0.165mmol), DMF (1mL) and a 60 % dispersion of sodium hydride (0.132mmol) in mineral oil. The resulting reaction mixture was stirred at room temperature for 1h. An aliquot was diluted with wet methanol and analyzed by LCMS. The reaction mixture was quenched with wet DMF and purified by reverse phase HPLC to obtain compound 26.

With the rapid development of chemical substances, we look forward to future research findings about 75279-39-9.

Reference:
Article; Harikrishnan, Lalgudi S.; Warrier, Jayakumar; Tebben, Andrew J.; Tonukunuru, Gopikishan; Madduri, Sudhakara R.; Baligar, Vishweshwaraiah; Mannoori, Raju; Seshadri, Balaji; Rahaman, Hasibur; Arunachalam; Dikundwar, Amol G.; Fink, Brian E.; Fargnoli, Joseph; Fereshteh, Mark; Fan, Yi; Lippy, Jonathan; Ho, Ching-Ping; Wautlet, Barri; Sheriff, Steven; Ruzanov, Max; Borzilleri, Robert M.; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 1026 – 1034;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84487-03-6 ,Some common heterocyclic compound, 84487-03-6, molecular formula is C5H4ClN3O2, 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.

General procedure: TAPEHA-Pd (0.015 g) was added to a solution of nitroarenes (1.0 mmol) in EtOH (20 mL). After N2H4 .H2O(4.0 mmol) was added the color of the catalyst was turned to black rapidly in the same way as reducing with NaBH4 . This color change means formation of palladium nanoparticles43 TAPEHA-PdNPs as mentioned above. After being stirred for 20 min at room temperature and atmospheric pressure, the catalyst was removedby ltering and EtOH was removed under a vacuum.

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. 84487-03-6, 6-Chloro-5-nitropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Genc, Hayriye; Zengin, Mustafa; Kuecuekislamo?lu, Mustafa; Imamoglu, Mustafa; Toplan, Hueseyin Oezkan; Arslan, Mustafa; Turkish Journal of Chemistry; vol. 41; 5; (2017); p. 784 – 792;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 823221-93-8, 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.823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, molecular weight is 260.44, as common compound, the synthetic route is as follows.

Prepared using General Procedure 17: To a stirred a solution of 5- bromo-2-chloro-4-(trifluoromethyl)pyridine (150 mg, 0.576 mmol) in acetonitrile (2 mL) was added sodium iodide (518 mg, 3.45 mmol). The reaction mixture was heated to 40C and acetyl chloride (26.0 mg, 0.345 mmol) was added. The reaction mixture was stirred at 40C for 90 min. Once cooled, the reaction was quenched with NaHC03 (5 mL) and extracted with EA (3 x 5 mL). The combined organics were washed with brine (10 mL), dried over MgS04 and concentrated to give 80.0 mg (40%) of 5-bromo- 2-iodo-4-(trifluoromethyl)pyridine as a white crystalline solid which was used in the subsequent step without purification. LCMS-ESI (m/z) calculated for C6H2BrF3IN: 351.9; found 352.5 [M+H]+, tR = 3.91 min. (Method 1).

Statistics shows that 823221-93-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; RECEPTOS, INC.; BOEHM, Marcus, F.; MARTINBOROUGH, Esther; MOORJANI, Manisha; TAMIYA, Junko; HUANG, Liming; YEAGER, Adam, R.; BRAHMACHARY, Enugurthi; FOWLER, Thomas; NOVAK, Andrew; MEGHANI, Premji; KNAGGS, Michael; WO2013/90454; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To degassed dioxane (10mL) were added sequentially 5- trifluoromethylpyridin-3-amine (2) (309mg, 1.9mmol), 2-chloropyrazine (1) (0.26mL, 2.86mmol), Pd2(dba)3 (52mg, 0.06mmol), XantPhos (66mg, 0.1 1 mmol) and Cs2C03 (1.24g, 3.8mmol) with continued degassing. The reaction mixture was heated up to 90C overnight. An additional portion of 2-chloropyrazine (0.17ml_, 1.91 mmol) was then added and the reaction mixture was heated up to (0304) 90C overnight. Once cooled down to rt, it was poured into H20 (20ml_) and extracted with EtOAc (3 x 20ml_). The combined organic extracts were dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/EtOAc (1 :0-1 :2) gave a residue which was re- dissolved in CH2CI2/MeOH (4:1 , 50ml_) and swirled with MP-TMT resin (440mg, 1.3mmol/g) at rt overnight. The solution was filtered, the resin washed with CH2CI2/MeOH (4:1 , 100ml_) and the filtrate concentrated in vacuo to yield (3) as a yellow solid (202mg, 44%). (0305) LCMS (ES): Found 241.0 [M+Hf. (0306) 1H NMR (300 MHz, DMSO-cf6), d: 10.14 (s, 1 H), 9.00 (d, J=2.4 Hz, 1 H), 8.69 (t, J= 2.0 Hz, 1 H), 8.52 (d, J=0.9 Hz, 1 H), 8.32 (d, J=1.5 Hz, 1 H), 8.25 (dd, J= 2.8, 1.5 Hz, 1 H), 8.08 (d, J= 2.8 Hz, 1 H). (0307) 19F NMR (282 MHz, DMSO-cf6), d: -61.09 (s, 3F).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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.

General procedure: 4-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)phenol (Intermediate C, 80mg, 0.30mmol) was dissolved in DMF (lmL) and potassium 2-methylpropane-2-olate (1M in THF, 0.33mL, 0.33mmol) was added dropwise. The mixture was stirred for 5min and a solution of 3-(bromomethyl)-5-methylisoxazole (63.2mg, 0.36mmol) in DMF (0.5mL) was added. The resulting mixture was stirred for 30min and directly purified by column chromatography (Si02, hexane/ethyl acetate). Fraction containing the product were concentrated under reduced pressure and further purified by reversed phase flash chromatography (C18, acetonitrile/water) to yield 3-(3-(4-((lH-pyrazol-l-yl)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine (7lmg, 0.20mmol, 66%) as a white solid. 400 MHz l NMR (CDCl3) d 8.13 (s, 1H), 7.70 (dd , J= 7.7, 1.8 Hz, 1H), 7.24 – 7.16 (m, 2H), 6.98 – 6.89 (m, 2H), 6.70 (dd, J= 7.7, 4.8 Hz, 1H), 6.23 (s, 1H), 6.10 (d, J= 1.1 Hz, 1H), 5.44 (s, 2H), 5.09 (s, 2H), 3.99 (s, 2H), 2.42 (d, .7= 0.9 Hz, 3H). MS: 363.3 [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,135450-23-6, its application will become more common.

Reference:
Patent; AMPLYX PHARMACEUTICALS, INC.; TRZOSS, Michael; COVEL, Jonathan; SHAW, Karen Joy; WEBB, Peter; (240 pag.)WO2019/113542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 92992-85-3, 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 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 11b was prepared from 2-bromo-3,5-dimethylpyridine (9b) and 10 in a manner similar to that described for compound 11a, with a yield of 68% as a brown syrup. 1H NMR(DMSO-d6) d 2.29 (s, 3H), 2.30 (s, 3H), 4.55 (d, 2H, J = 5.7 Hz),5.21 (t, 1H, J = 5.7 Hz), 7.38 (d, 2H, J = 8.3 Hz), 7.47 (d, 2H,J = 8.3 Hz), 7.52 (br s, 1H), 8.30 (br s, 1H); MS (ESI) m/z 214 [M+H]+.

According to the analysis of related databases, 92992-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Narazaki, Fumie; Shiina, Yasuhiro; Seo, Ryushi; Amano, Yasushi; Mihara, Takuma; Moriguchi, Hiroyuki; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3351 – 3367;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem