Category: pyridine-derivatives

Synthetic Route of 6980-09-2 ,Some common heterocyclic compound, 6980-09-2, molecular formula is C6H5ClN2O3, 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.

4-methoxy-2-(4-methyl-1H-imidazol-1-yl)-3-nitropyridine To a mixture of 2-chloro-3-nitro-4-methoxypyridine (2.0 g, 10.6 mmol) and 4-methylimidazole (1.3 g, 15.9 mmol) in 20 mL of DMF was added freshly powdered KOH (0.9 g, 15 mmol). The resulting mixture was stirred at rt for 16 h. The reaction was poured into water and extracted with ethyl acetate (3*). Standard work-up followed by column chromatography using 50% ethyl acetate in hexane provided the product (0.65 g, 28% yield). MS (ESI) 235.0 [M+H]+

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. 6980-09-2, 2-Chloro-4-methoxy-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; US2010/120762; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10177-29-4, name is 4-Chloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 10177-29-4

Intermediate4-(2,5-Dichloro-phenoxy)-nicotinic acidTo a suspension of 10 g (63.47 mmol) 4-chloronicotinic acid (commercially available; CAS RN10177-29-4) and 11.38 g (69.81 mmol) 2,5-dichlorophenol (commercially available CAS RN 583-78-8) in 50 mL dry N,N-dimethylformamide were added 17.55 g (126.94 mmol) potassium carbonate, 1.21 g (6.35 mmol) copper(I) iodide and 1.21 g (19.04 mmol) copper nanopowder. The green suspension was stirred at 120 C. (oil bath temperature) for 3 hours and then cooled down to 80 C. At that temperature, 400 mL water were added, the suspension was stirred at 80 C. for 5 min., filtered over Dicalite speed plus (Acros) and the filter cake washed twice with 50 mL water. The resulting filtrate was extracted three times with ethyl acetate and then the pH was adjusted to 4-5 using 140 mL 1M aqueous hydrochloric acid. The resulting green, turbid solution was treated with ethyl acetate, stirred for 5 min. and filtered. The blue solid that had formed was filtered off and the layers of the filtrate were separated. The aqueous layer was saturated with solid sodium chloride and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. To the resulting solid 200 mL saturated aqueous potassium carbonate solution and 200 mL ethyl acetate were added. The aqueous layer was extracted twice with 200 mL ethyl acetate and the pH was adjusted to 4 using 25% aqueous hydrochloric acid. The resulting suspension was extracted three times with ethyl acetate. The combined organic layers were washed three times with water and once with brine, dried over magnesium sulfate, filtered and evaporated to give the desired compound as a light brown solid (7.29 g, 40%). MS (ESI): m/z=281.8 [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, 10177-29-4, 4-Chloronicotinic acid.

Reference:
Patent; Bissantz, Caterina; Dehmlow, Henrietta; Erickson, Shawn David; Kim, Kyungjin; Martin, Rainer E.; Sander, Ulrike Obst; Pietranico-Cole, Sherrie Lynn; Richter, Hans; Ulmer, Christoph; US2011/178089; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59352-90-8, 5-Bromo-6-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, Formula: C6H8BrN3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

5-Bromo-6-methylpyridine-2,3-diamine (50 mg, 0.25 mmol), 4-chlorophenylboronicacid (45 mg, 0.29 mmol), and cesium carbonate (240 mg, 0.74 mmol) were suspendedin dioxane/water (4:1; v/v) (1.25 ml) and this mixture was degassed (3 x vacuumnitrogen cycles). [1,1 ?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1)dichloromethane complex was added and the mixture degassed again (3 x vacuum30 nitrogen cycles). The resulting reaction mixture was stirred at 110 00 for 16 h. Then, the mixture was allowed to cool and it was worked-up adding chloroform and washing with water and brine. The organic phase was dried and evaporated under reduced pressure to afford a residue of 93 mg. This crude material was purified by flash chromatography (methanol-dichloromethane gradient, 0:100 rising to 10:90) to give 46mg (0.20 mmol, 80percent yield) of the title compound as a solid. Purity 95percent.1H NMR (400 MHz, CHLOROFORM-d) oe ppm 7.35 (d, 2H, J = 8.3 Hz), 7.20 (d, 2H, J =8.3 Hz), 6.78 (s, 1 H), 4.30 (br.s, 2H), 3.23 (br.s, 2H), 2.28 (s, 3H)UPLC/MS (3mm) retention time 1.08 mm.LRMS: m/z 234 (M+1, ixCI).

The synthetic route of 59352-90-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; CATURLA JAVALOYES, Juan Francisco; (110 pag.)WO2017/64068; (2017); 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. 85148-26-1, name is 3-Chloro-5-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Chloro-5-(trifluoromethyl)pyridine

General procedure: Under an N2 atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol %), dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol) were successively added into a Schlenk tube. The mixture was stirred vigorously at 90 C for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: PE/EA = 15:1) to give the pure products. The reported yields are the average of two runs.

The synthetic route of 85148-26-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Saranya, Gandhi; Viswanathamurthi, Periasamy; Bertani, Roberta; Sgarbossa, Paolo; Malecki, Jan Grzegorz; Journal of Organometallic Chemistry; vol. 831; (2017); p. 1 – 10;,
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.100-55-0, name is 3-Pyridinemethanol, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.Computed Properties of C6H7NO

General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5mol%), Bi(OTf)3 (0.05mol, 5mol%), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mixture was stirred at 60C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-55-0, 3-Pyridinemethanol, and friends who are interested can also refer to it.

Reference:
Article; Hu, Yongke; Li, Bindong; Tetrahedron; vol. 73; 52; (2017); p. 7301 – 7307;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 118650-08-1, 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. 118650-08-1, name is Methyl 2-(5-bromopyridin-3-yl)acetate, molecular formula is C8H8BrNO2, 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.

(5-Bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 30 mg, 0.149 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.020 mmol), potassium phosphate (63 mg, 0.297 mmol) and water (0.2 mL) were added to a solution of (E)-1-(4-{1-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-3-ethyl-1-penten-3-ol (Example 38-(6); 50 mg, 0.099 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100C for 2.5 hours. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate = 1:1) to give the target compound as a colorless oil (12.5 mg, 24%). 1H-NMR (chloroform-d): 0.66 (6H, t, J=7.26Hz), 0.93 (6H, t, J=7.25Hz), 1.65 (4H, q, J=7.34Hz), 1.98 (6H, s), 2.11 (4H, q, J=7.42Hz), 2.35 (3H, s), 3.68 (2H, s), 3.72 (3H, s), 6.03 (1H, d, J=15.99Hz), 6.76 (1H, d, J=16.00Hz), 6.91 (2H, s), 6.97-7.01 (2H, m), 7.33 (1H, d, J=7.91Hz), 7.49 (1H, s), 8.35 (1H, d, J=2.14Hz), 8.47 (1H, d, J=2.14Hz).

According to the analysis of related databases, 118650-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 757978-18-0, 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]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, 757978-18-0, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

100 mL round bottom flaskIodo-1H-pyrrole [2,3-b] pyridine (M1) (100.0 mg, 3.1 mmol)20 mL of dichloromethane, triethylamine (930 mg, 9.2 mmol), DMAP (40 mg, 0.31 mmol),Benzenesulfonyl chloride (N1) (1100 mg, 6.2 mmol) was dissolved in 10 mL of dichloromethane under ice-cooling,Dropping funnel through the constant pressure drop into the solution, the drop is completed, stirring at room temperature 1h,TLC detection, no M1 remaining, washed 3 times, liquid separation, the organic phase anhydrous sodium sulfate drying,The solvent was removed by concentration and recrystallized from ethyl acetate (5 mL) to give a white solid which was dried to give 5-bromo-3-iodo-1- (phenylsulfonyl) -1H-pyrrole [2,3-b] pyridine (B8).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,757978-18-0, its application will become more common.

Reference:
Patent; Fudan University; Zhou, Yaming; Yang, Chengbin; Hong, Hui; Liu, Xiaofeng; Yang, Yongtai; Ling, Yun; Gu, Yu; Deng, Mingli; (38 pag.)CN106117181; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 733757-89-6, tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate, 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, 733757-89-6, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl 3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate

Description 21 : 6-methyl-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4- c] pyridineUnder an inert atmosphere of argon, LiAIH4 (2.3 M in THF; 7.5ml; 17.3mmol) was added dropwise over 2 minutes to a cool (O0C) stirring solution of 6-tert-butoxycarbonyl-3- (trifluoromethyl)-4,5,6,7-tetrahydro-1 H-pyrazolo[3,4-c]pyridine (2.0Og; 8.45mmol) in anhydrous THF (42ml). The resulting mixture was stirred in an oil bath at 580C for 17 hours, cooled to O0C, and quenched by the careful addition of an aqueous solution of sodium potassium tartrate (1 M; 50ml). After stirring at room temperature for 1 hour, the mixture was diluted with diethyl ether (50ml) and more aqueous sodium potassium tartrate (1 M; 50ml). After stirring at this temperature for a further 1 hour, the mixture was partitioned between water (100ml) and diethyl ether (200ml). The separated aqueous phase was extracted with ethyl acetate (200ml), and the combined organic phase was dried (MgSO4) and concentrated in vacuo. The resulting off-white solid (1.39g) was purified using an SCX column giving the title compound as a yellow solid (1.23g; 6.01 mmol)LC/MS (ES): Found 206 (ES+), retention time 1.81 mins. C8H10F3N3 requires 205.1 H-NMR (400MHz, CDCI3): 2.48 (3H, app s), 2.74 (4H, app s), 3.58 (2H, app s), 5.01(1 H, br s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,733757-89-6, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/113795; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 141-86-6, 2,6-Diaminopyridine, 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, Application In Synthesis of 2,6-Diaminopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2,6-Diaminopyridine

In a 100 mL three-necked round bottom flask, acetic anhydride (2.1 ml, 27.5 mmol) in 20 mL THF was added dropwise to a stirred mixture of pyridine-2,6-diamine (3.00 g, 27.5 mmol) and triethylamine (2.78 g, 27.5 mmol) in THF (40 ml) at 0C. After the reaction mixture was stirred at room temperature overnight, it was diluted with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine (2 x 1 OmL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum ether (10/i) to give the title compound as a solid. LCMS (ESI) calc?d for C7H9N30 [M+i ]: 152 found: 152; ?H NMR (300 MHz, CD3OD): oe7.38-7.32(m, 1H),718(d, J= 7.8 Hz, 1H), 6.24 (d,J= 8.1 Hz, 1H),2.08(s,3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,141-86-6, 2,6-Diaminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60290-21-3, 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. 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, 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.

4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in was dissolved in DMF (7.0 ml). After cooling to 0C, N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a darkbrown solid (455 mg). Physical properties: m/z[M+H]+ 279.1

According to the analysis of related databases, 60290-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SAGARA, Takeshi; ITO, Satoru; OTSUKI, Sachie; SOOTOME, Hiroshi; EP2657233; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem