Category: pyridine-derivatives

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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C19H16BrNO2

To a stirred solution of 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzo[d]thiazole (36-2) (1.1 g, 3.99 mmol) and 2,6-bis(benzyloxy)-3-bromopyridine 25-1 (1.9 g, 5.13 mmol) in a sealed tube, in Dioxane (20 mL ) and Water (2 mL ), was added K3PO4 (2.1 g, 9.12mmol) and the solution was degassed for 10 min. PdCl2(dppf)-DCM (0.400 g, 489 mumol) was added and again the solution was degassed for 5 min. After degassing completion, the sealed tube was closed with a teflon cap and the reaction mixture was stirred at 80c for 16 h. After reaction completion, as checked by TLC, the reaction mixture was filtered through celite. The organic layer was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography eluted with 5 to 20 % ethyl acetate in hexane to provide 5- (2,6-Bis-benzyloxy-pyridin-3-yl)-2-methyl-benzothiazole (36-3) (1.0 g, 2.28 mmol, 57% yield). LC MS: ES+ 439.3.

The synthetic route of 16727-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); 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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.Application In Synthesis of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

To a stirred solution of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (10 g, 29.21 mmol) in 1,4-dioxane (50mL), 4N HCI solution in dioxane (100 mL, 10V) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residue was washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, 1 H), 7.82 (dd, J = 9.2, 2.4 Hz, 1 H), 6.99 (d, J = 9.2 Hz, 1 H), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 min, 99.3 % (Max).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55404-31-4, 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.55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

3-Bromo-2-(4-methoxybenzyloxy)-4-methylpyridine 3-bromo-2-(4-methoxybenzyloxy)-4-methylpyridine was prepared by the procedure described in J. Med. Chem., 2008, 51, 3065. A pressure vessel was charged with anhydrous THF (25 ml) and sodium hydride (1.44 g, 36.18 mmol, 60% dispersion). To this stirred mixture was added portionwise a solution of 4-methoxybenzyl alcohol (5.0 g, 36.18 mmol) in anhydrous THF (15 ml). After addition was complete, the mixture was stirred at room temperature for 30 minutes and a solution of 3-bromo-2-chloro-4-picoline (4.97 g, 24.08 mmol) in anhydrous THF (15 ml) was added. The vessel was sealed and the reaction mixture was heated at 75 C. for 6 hours. Upon cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with water, sat’d NaCl(aq.), dried over MgSO4, filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc) gave the title compound as a clear oil which crystallized on standing (6.71 g, 90%).

The chemical industry reduces the impact on the environment during synthesis 55404-31-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Allergan, Inc.; Wurster, Julie; Yee, Richard; Hull III, Clarence Eugene; Malone, Thomas C.; (39 pag.)US2016/96832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1064783-29-4 ,Some common heterocyclic compound, 1064783-29-4, molecular formula is C5H2ClFN2O2, 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.

5-Chloro-3-fluoro-2-nitropyridin (190.0 mg, 1.08 mmol) and hydrazine monohydrate (80.0 muL, 1.61 mmol) were dissolved in EtOH (3.0 mL) and the mixture was stirred at room temperature for 2 hours. Et2O was added thereto to form a solid, and the formed solid was filtered to obtain orange solid compound of 5-chloro-3-hydrazinyl-2-nitropyridine (170.0 mg, 84%). [1074] 1H-NMR (300 MHz, DMSO-d6); delta: 9.06 (brs, 1H), 8.10 (m, 1H), 7.76 (d, 1H, J=2.4 Hz)

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. 1064783-29-4, 5-Chloro-3-fluoro-2-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; C&C RESEARCH LABORATORIES; Ho, Pil Su; Yoon, Dong Oh; Han, Sun Young; Lee, Won Il; Kim, Jung Sook; Park, Woul Seong; Ahn, Sung Oh; Kim, Hye Jung; US2014/315888; (2014); 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 947179-03-5, name is Ethyl 4-bromo-6-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 947179-03-5

Step 5: 4-Bromo-6-methyl-pyridine-2-carboxylic acid (4-methyl-thiazol-2-yl)-amide To a solution of 3.72 g (32.6 mmol) of 2-Amino-4-methylthiazole in 40 ml of dry dioxane were added dropwise 15.9 ml (31.8 mmol, 4.0 equiv.) of a 2M solution of trimethylaluminium in hexane. The solution was stirred for 30 min at room temperature. Then a solution of 1.94 g (7.95 mmol) of 4-Bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester in 6 ml of dry dioxane was added dropwise and the reaction was heated to 100 C. for 1.5 h. The reaction was quenched by cautious addition of 2.5 ml of water. Then approximately 10 g of anhydrous sodium sulfate were added to bind the water and the mixture was stirred vigorously for 5 min. The mixture was diluted by addition of 20 ml of methylene chloride and filtered over Speedex filteraid which was washed with methylene chloride. The filtrate was concentrated in vaccuo and the residue was purified by flash chromatography (heptane/ethyl acetate 4:1) to yield the title compound (1.95 g, 79%) as a yellow solid, MS (ISP): m/e=312.0, 314.0 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 947179-03-5.

Reference:
Patent; Jaeschke, Georg; Spooren, Will; Vieira, Eric; US2007/197553; (2007); 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.135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.category: pyridine-derivatives

General procedure: Reference Example 24 6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile [0267] To a solution of 5-methoxy-2-phenyl-1H-indole (200 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (dispersed in liquid paraffin, 50% or more, 45 mg) under ice-cooling. This mixture was stirred for 30 minutes at room temperature. Subsequently, 6-chloromethylpyridine-2-carbonitrile (216 mg) was added thereto, followed by stirring at 80C overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (228 mg). [0268] 1H-NMR (DMSO-d6) delta ppm: 3.77 (3H, s), 5.55 (2H, s), 6.55-6.65 (1H, m), 6.77 (1H, dd, J = 2.4, 8.8 Hz), 6.91 (1H, dd, J = 1.5, 7.4 Hz), 7.13 (1H, d, J = 2.4 Hz), 7.26 (1H, d, J = 8.8 Hz), 7.35-7.55 (5H, m), 7.85-7.95 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Kyorin Pharmaceutical Co., Ltd.; TATANI, Kazuya; KONDO, Atsushi; KONDO, Tatsuhiro; KAWAMURA, Naohiro; SETO. Shigeki; KOHNO, Yasushi; EP2669271; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156072-84-3 ,Some common heterocyclic compound, 156072-84-3, 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.

To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH (110 mL of 5 N solution, 550 mmol). The resulting mixture was refluxed at 90 C. for 18 h. After cooling to RT, the reaction mixture was concentrated. The residue was diluted with water and the pH of the solution was adjusted to 4 by addition of 5 N HCl. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2×). The aqueous layer was again acidified with 5 N HCl to pH 4 and extracted with EtOAc (2×). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C. for 12 h to give 5-chloro-3-methylpicolinic acid (268) (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z=172.0 (M+H)+. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.29 (br. s., 1H), 8.41 (d, J=1.76 Hz, 1H), 7.73 (d, J=1.76 Hz, 1H), 2.75 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); 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. 1073159-75-7, name is N-(3-(Aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide acetate, molecular formula is C10H17N3O4S, 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. name: N-(3-(Aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide acetate

Step 2. A solution of tert-butanol (20.0 mL), DCE (20.0 mL) and DIEA (3.13 mL, 18.0 mmol) was treated with C8 (5.60 g, 15.0 mmol) and B5 (5.02 g, 15.0 mmol), and the resulting mixture was stirred at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was cooled to 25 C. and concentrated. The resultant residue was partitioned between EtOAc and 1 N sodium hydroxide, and the organic phase was collected. The aqueous layer was extracted with EtOAc, and the combined organic phases were dried over MgSO4 and filtered. The resultant filtrate was concentrated under reduced pressure, and the resultant residue was triturated with hot EtOAc to provide 9 as a white solid. Yield: 7.83 grams, 95%. LC/MS (standard) 250=3.0 min., m/z 553.6 (MH+). HPLC (FAK1) 250=8.14 min. 1H NMR (d6-DMSO) : 9.75 (bs, 1H), 8.44 (d, J=5.2 Hz., 1H), 8.29 (s, 1H), 8.05 (bs, 1H), 7.82 (d, J=7.8 Hz., 1H), 7.60 (t, J=5.7 Hz., 1H), 7.44-7.40 (m, 2H), 7.17 (t, J=5.7 Hz, 1H), 4.82 (d, J=5.7 Hz., 2H), 3.16 (s, 3H), 3.13 (s, 3H), 1.51 (s, 9H) ppm. FAK IC50: 0.0006 muM

With the rapid development of chemical substances, we look forward to future research findings about 1073159-75-7.

Reference:
Patent; Pfizer Inc.; US2009/54395; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886364-94-9, 5-Bromo-4-methylpicolinaldehyde, 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, COA of Formula: C7H6BrNO, blongs to pyridine-derivatives compound. COA of Formula: C7H6BrNO

To a solution of ethylene glycol (310 mg, 5.00 mmol, 280 pL, 2.00 equiv), 5-bromo-4- methyl-pyridine-2-carbaldehyde (500 mg, 2.50 mmol, 1.00 equiv) in toluene (20.0 mL) was added / oluenesul fonic acid (47.6 mg, 250 pmol, 0.10 equiv). The mixture was stirred at 110 C for 12 h and was subsequently concentrated in vacuo to give a residue. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate = 1/0 to 5: 1) to afford 5-bromo- 2-(l, 3-dioxolan-2-yl)-4-methylpyridine (320 mg, 1.24 mmol, 49.6% yield) as a colorless oil. 1H NMR (400MHz, CDCI3) d = 8.64 (s, 1H), 7.42 (s, 1H), 5.80 (s, 1H), 4.19 – 4.14 (m, 2H), 4.10 – 4.05 (m, 2H), 2.42 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886364-94-9, 5-Bromo-4-methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MIRATI THERAPEUTICS, INC; MARX, Matthew, Arnold; LEE, Matthew, Randolph; BOBINSKI, Thomas, P.; BURNS, Aaron, Craig; ARORA, Nidhi; CHRISTENSEN, James, Gail; KETCHAM, John, Nichael; (225 pag.)WO2019/152419; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15103-48-7 ,Some common heterocyclic compound, 15103-48-7, molecular formula is C5H5NO3S, 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.

1 g of the compound Slic-CJH-5 prepared in the fourth step of Example 2,And 200mgof2-pyridine sulfonic acid and 530 mg of anhydrous sodium carbonate were dispersed in 40 ml of ethylene glycol ether,Under nitrogen protection,The temperature was refluxed for 12 hours,Cooled to room temperature, diluted with dichloromethane, washed three times with water, dried in organic phase,Filtered, the filtrate was concentrated under reduced pressure,The residue was purified by silica gel column and recrystallized from ether-petroleum ether,To obtain 460 mg of the compound Slic-CJH-DB011-VII02,Yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15103-48-7, its application will become more common.

Reference:
Patent; Shijiazhuang Chengzhi Yonghua Xianshi Material Limited Company; Cao, Jianhua; Pang, Hui; Huang, Hongliang; Hua, Ruimao; (36 pag.)CN103896990; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem