Pyridine-derivatives

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. 106984-91-2, name is 6-Oxo-1,6-dihydropyridine-3-carbaldehyde, molecular formula is C6H5NO2, 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. Application In Synthesis of 6-Oxo-1,6-dihydropyridine-3-carbaldehyde

A solution of 6-hydroxynicotinaldehyde SM 1(192mg, 4 mmol) and (S)-1-cyclopropylethanamine (170 mg, 2 mmol) in DCM (5 mL) and EtOH (5 mL) was added NaBH3CN(620 mg, 10 mmol), then stirred at RT for 16 h. The resulting reaction mixture was quenched withwater and extracted with DCM, dried and evaporated, purified by combiflash (methanol:DCM =1:20) to give compound 1(300mg, 78%). LC-MS: m/z = 193.1 [M+H]

With the rapid development of chemical substances, we look forward to future research findings about 106984-91-2.

Reference:
Patent; ABBVIE INC.; MICHAELIDES, Michael; HANSEN, Todd; DAI, Yujia; ZHU, Guidong; FREY, Robin; GONG, Jane; PENNING, Thomas; CURTIN, Michael; MCCLELLAN, William; CLARK, Richard; TORRENT, Maricel; MASTRACCHIO, Anthony; KESICKI, Edward A.; KLUGE, Arthur F.; PATANE, Michael A.; VAN DRIE, John H. Jr.; JI, Zhiqin; LAI, Chunqiu C.; WANG, Ce; (1190 pag.)WO2016/44770; (2016); 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 17282-03-0, name is 3-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 131.4: 3-Bromo-2-methoxy-5-methyl-pyridine To a solution of 3-bromo-2-chloro-5-methylpyridine (5 g, 24.2 mmol) in MeOH (80 mL) was added a solution of sodium methoxide 5.4M in MeOH (25 mL, 135 mmol) and the mixture was stirred at 65C for 32 h. The resulting suspension was filtered and the mother liquor was concentrated. Et20 and H20 were added and the phases were separated. The organic layer was washed with H20 and brine, dried (MgS04), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc: 90: 10? 0:100) to afford the title compound. tR: 1.03 min (LC-MS 2).

With the rapid development of chemical substances, we look forward to future research findings about 17282-03-0.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55676-21-6 ,Some common heterocyclic compound, 55676-21-6, molecular formula is C7H6ClNO, 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.

A solution of 1-(2-chloropyridin-3-yl)ethanone (B-2) (6 g, 38.6 mmol) and hydrazine (85%, 9.1 g, 154.4 mmol) in pyridine (80 mL) was stirred under reflux overnight. The mixture was cooled to room temperature, concentrated, diluted with water (80 mL) and then extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine, dried over Na2S04, and concentrated under vacuo. The resulting residue was used for the next step without furtuer purification. MS (m/z): 134 (M+1 )+

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. 55676-21-6, 1-(2-Chloropyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82671-06-5, Adding some certain compound to certain chemical reactions, such as: 82671-06-5, name is 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid,molecular formula is C6H2Cl2FNO2, 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 82671-06-5.

To a round-bottomed flask under a N2 atmosphere were added degassed DMF (270 mL), Pd(OAc)2 (0.05 eq, 2.7 g, 11.9 mmol), PPh3 (0.1 eq, 6.2 g, 23.8 mmol), and degassed Et3N (6 eq, 200 mL, 1428.6 mmol). The mixture was stirred for 20 minutes, HCOOH (3 eq, 28 mL, 714.3 mmol) was then added. 5 minutes later, 2,6-dichloro-5-fluoronicotinic acid (50 g, 238.1 mmol) was added. The mixture was stirred at 50 C. The reaction was followed by analysis (1H NMR) of a worked-up aliquot. When all starting material was consumed (24 h), the mixture was cooled to 0 C. and water (500 mL) was added. After 20 minutes, The mixture was filtered through a pad of Celite that was rinsed with water. The mixture was basified to pH 9 with 30% aq. NaOH and washed with EtOAc (2*). HCl (12 N) was added slowly to pH 1 and the solution was saturated with NaCl. The mixture was extracted with EtOAc (3*). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give 37 g (88%) of a beige solid used in the next step without further purification. 1H NMR (DMSO-d6, 300 MHz): delta 8.16 (dd, 1H); 8.58 (d, 1H).

According to the analysis of related databases, 82671-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; US2011/20377; (2011); 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 175205-81-9, name is 2-Bromo-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H3BrF3N

A 5mL microwave vial flushed with Argon was charged with 2-bromo-4-(trifluoromethyl)pyridine (0.0923 mL, 0.724 mmol), 5-cyclopropyl-2-[3-ethylsulfonyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl )-2-pyridyl]-3-m ethyl-6-(trifluoromethyl)im idazo[4 , 5-c]pyrid in-4-one (Step A, 0.2 g), tetrakis(triphenylphosphine) palladium(0) (0.042 g, 0.036 mmol), potassium phosphate tribasic (0.48 g, 2.17 mmol), toluene (2.9 mL) and water (2.9 mL). The mixture was then heated 30 at 110°C under microwave. The reaction mixture was diluted with water and ethyl acetate then, after separation of the phases, the aqueous phase was extracted two time with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated under vacuum. The residue was subjected to columnchromatography over silica gel, eluting with ethyl acetate cyclohexane. The selected fractions were evaporated to yield the title compound as a white solid (0.11 g). 1H NMR (400 MHz, CDCI3) oe ppm 1.08 (m, 2H), 1.30 (m, 2H), 1.40 (t, 3 H), 3.11 (m, 1 H), 3.85(q, 2 H), 4.09 (s, 3 H), 7.20 (s, 1 H), 7.65 (d, 1 H), 8.11 (s, 1 H), 9.00 (d, 1 H), 9.11 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 175205-81-9.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; MUEHLEBACH, Michel; HALL, Roger, Graham; (106 pag.)WO2017/89190; (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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid, the common compound, a new synthetic route is introduced below. Quality Control of 3-Chloro-5-(trifluoromethyl)picolinic acid

(1) Add 2 mmol) to a 25 ml three-necked flask3,5-Difluoro-5-(trifluoromethyl)picolinic acid8.0 mmol) pyridine and 5 ml acetonitrile, and the ice bath was cooled down to -5C. Then, 0.51 g (4.43 mmol) of methanesulfonyl chloride was slowly added dropwise to the system using a constant pressure dropping funnel. The mixture was stirred for 10 min after the addition was completed, and the mixture was once injected into the system. 3 mmol) 2-amino-3,5-difluorobenzoic acid was added, and after stirring for 10 min, 9 mmol) of pyridine was slowly added dropwise using a constant pressure dropping funnel. The dropping process should keep the temperature below 0C. Continue stirring after the addition was complete. 15min, then continue to slowly add 4.5mmol of methanesulfonyl chloride with a constant pressure dropping funnel, stir for 1h after dropping is completed, remove the ice salt bath, the reaction temperature slowly rises to room temperature, after 12h reaction, add water and dichloromethane extraction The organic layer was passed through a column (petroleum ether: ethyl acetate = 10: 1) to give the intermediate 6,8-difluoro-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl) -4H-benzo[d][1,3]oxazin-4-one.

The synthetic route of 80194-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guizhou University; Wu Jian; Xu Fangzhou; Wang Yanyan; Yu Gang; Xue Wei; Shi Jun; (24 pag.)CN107759518; (2018); A;,
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.109345-94-0, name is 5-Methoxypyridin-3-ol, molecular formula is C6H7NO2, molecular weight is 125.13, as common compound, the synthetic route is as follows.COA of Formula: C6H7NO2

Step 1 3-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy)-5-methoxypyridine (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimeth yl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin (1.00 g, 2.43 mmol) was dissolved in N,N-dimethylformamide (10.00 mL), followed by successive addition of potassium carbonate (671.70 mg, 4.86 mmol) and 5-methoxypyridin-3-ol (334.47 mg, 2.67 mmol), then stirred at 80 C. for 12 hours. The reaction was quenched by adding 10 mL water and then extracted with ethyl acetate (20.00 mL*3). The organic phase was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by column chromatography (silica, petroleum ether/ethyl acetate=10/1 to 2/1) to give 3-(2-((3R,4aR,6aS,7R,10 bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy)-5-methoxypyridine 442 (700 mg, yield: 63.37%). MS m/z (ESI): 456.6[M+1] 1H NMR (400 MHz, CDCl3) 7.91 (d, J=8 Hz, 2H), 6.69 (t, J=4.4 Hz, 1H), 4.89 (s, 1H), 4.59 (t, J=6 Hz, 2H), 4.08-4.02 (m, 2H), 3.84 (s, 4H), 3.51-3.43 (m, 2H), 2.44-2.40 (m, 2H), 2.05-2.01 (m, 3H), 1.88-1.83 (m, 4H), 1.60 (s, 3H), 1.55-1.35 (m, 6H), 1.45-1.27 (m, 3H) 1.26-1.21 (m, 3H), 0.79 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109345-94-0, 5-Methoxypyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 186593-43-1, 5-Amino-3-bromo-2-methylpyridine, 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, 186593-43-1, blongs to pyridine-derivatives compound. Computed Properties of C6H7BrN2

4 – [(4-methyl-piperazin-1-yl) methyl] -3- (trifluoromethyl) benzoicacid (297 mg, 0.754 mmol), 2- (7- aza-benzotriazole ) -Nu, Nu, Nu ‘, Nu’-tetramethyluronium hexafluorophosphate (317 mg, 0.834 mmol) and N, N-diisopropylethylamine (0.17 mL, 1.043 mmol) was dissolved in N, N -dimethylformamide (5 mL) in. This mixture was added thereto and stirred atroom temperature for half an hour 5- bromo-6-methyl-3-aminopyridine (130 mg,0.695 mmol), stirred at room temperature continued overnight.After completionof the reaction by TLC, cooled to room temperature, water was added thereto,extracted with ethyl acetate, the organic phase was dried over anhydrous sodiumsulfate, filtered, and the solvent was evaporated to dryness, the residue waspurified by silica gel column chromatography to give N- (5- bromo – 6-methyl -pyridin-3-yl) -4- (4-methyl – piperazin-1-ylmethyl) -3-trifluoromethyl – benzamide(yellow solid, 80 mg)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,186593-43-1, its application will become more common.

Reference:
Patent; Shanghai Pharmaceuticals Holding Co.,Ltd .; WAN, HUIXIN; LI, CHUNLI; SHI, Chen; Liu, Haiyan; Li, Ping; XIA, Guangxin; HAN, Yanan; (52 pag.)CN103420977; (2016); B;,
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. 100-48-1, name is Isonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H4N2

a) To a solution of 0.23 g sodium in 40 ml methanol was added 10.62 g 4-cyanopyridine at room temperature. Stirring was continued for 6 h followed by the addition of 5.9 g ammoniumchloride and stirring was continued for another 10 h. Then 120 ml diethylether was added and the precipitate was filtered off after 30 min and washed once with 20 ml of diethylether. The product was dried under high vacuum. 14.95 g 4-amidino-pyridine hydrochloride was obtained as a white powder.

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, 100-48-1, Isonicotinonitrile.

Reference:
Patent; Bolli, Martin; Boss, Christoph; Clozel, Martine; Fischli, Walter; US2003/87920; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109-04-6, 2-Bromopyridine, 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, Product Details of 109-04-6, blongs to pyridine-derivatives compound. Product Details of 109-04-6

Example 1: Preparation of 2-(4-chloro-phenyl)pyridine; [53] Under a nitrogen stream, 5.0 g (0.032 mol) of 4-chloro-phenyl boronic acid, 10.0 g(0.064 mol) of 2-bromopyridine, 150 D of tetrahydrofuran and 2M potassium carbonate solution (20 D) were placed into a 2-neck round flask 250 D and then 0.37 g (3 mol%) of palladium tetrakistriphenylphosphine [(pd(PPh ) ] was added as a catalyst. After the resulting solution was heated to reflux at 8O0C for 24 hours, the reaction was terminated. The resulting mixture was poured into a beaker containing 200 D of distilled water. After extraction with ether (150 D) three times, 10 g of magnesium sulfate was added. The resulting solution was stirred by a rotary stirrer for 30 minutes and then the extraction mixture was filtered. After removing the solvent using a rotary evaporator, the residue was subjected to column chromatography using dichloromethane as a developing solvent and then distilled under reduced pressure to give the 2-(4-chloro-phenyl)pyridine. The yield was 56%.[54] The H-NHR spectrum is shown in Fig. 1 to confirm the structure of the thus prepared 2-(4-chloro-phenyl)pyridine.

The synthetic route of 109-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GWANGJU INSTITUTE OF SCIENCE AND TECHNOLOGY; WO2007/129810; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem