Pyridine-derivatives

Application of 108-99-6 ,Some common heterocyclic compound, 108-99-6, molecular formula is C6H7N, 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.

Example 2; The pelletized catalyst, TOSOH HSZ-690 HOD (SAR 203) with a silica binder, was ground to a coarse powder and screened to obtain a uniform size of 1-2 mm in diameter. A weight of 0.26 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. Operating at a chlorine feed of 5 cc/min, a beta-picoline feed rate of 0.13 mg/min (10 cc/min N2 with a chiller temperature of 10 C.), the reagents were fed to the reactor at an initial temperature of 250 C. The system was initially ramped up to 325 C. and allowed to stablize. Under these conditions the product gases were 18.5% 3-trichloromethylpyridine (beta-tri ) and 65.4% beta-2-tet. When the system was allowed to stabilized at 350 C. the amount of beta-tri in the product gases was reduced to 2.6% and the conversion to beta-2-tet increased to 68.6% (see Table 2).; Example 3; The catalyst, TOSOH HSZ-690 HOD (SAR 203) with the silica binder, was sized to a uniform particle size of 1-2 mm in diameter. A weight of 0.26 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. The reactor temperature was initially set to 250 C. prior to flowing chlorine at a rate of 5 cc/min. The beta-picoline feed rate was set to 0.13 mg/min (N2 flow 10 cc/min, chiller at 10 C.), while the reactor oven was ramped up to 350 C. over a one hour time period. At 350 C. the amount of beta-2-tet observed in the product gases was 65.6% (see Table 2).; Example 4; The catalyst, TOSOH HSZ-690 HOD (SAR 203) with the silica binder, was sized to a uniform particle size of 1-2 mm in diameter. A weight of 0.51 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. The reactor temperature was initially set to 250 C. prior to flowing chlorine at a rate of 5 cc/min. The beta-picoline feed rate was set to 0.13 mg/min (chiller at 10 C.), with a nitrogen flow of 10 cc/min, while the reactor oven was ramped up to 350 C. over 2 hours. When the system had stabilized at 350 C. the amount of beta-2-tet observed in the product gases was 71.7% (see Table 2).; Example 5; The catalyst, TOSOH HSZ-690 HOD (SAR 203) with the silica binder, was sized to a uniform particle size of 1-2 mm. A weight of 0.51 g of catalyst was charged into the reactor tube and glass wool (Pyrex) was used to secure it in place. The reactor temperature was initially set to 250 C. prior to flowing chlorine at a rate of 5 cc/min. The beta-picoline feed rate was set to 0.25 mg/min (N2 at 10 cc/min, chiller at 20 C.), while the reactor oven was slowly ramped up to 350 C. over 2 hours. When the system had stabilized at 350 C. the amount of beta-2-tet observed in the product gases was 66.9% (see Table 2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,108-99-6, its application will become more common.

Reference:
Patent; Campbell, Kent Douglas; Livingston, Dana Alan; Wan, Hawk Suewah; Larson, Kenneth Michael; Schoeman, Brian John; Lakso, Steven Roy; US2005/240024; (2005); A1;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 82205-58-1, 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. 82205-58-1, name is 1-(5-Nitropyridin-2-yl)piperazine. A new synthetic method of this compound is introduced below.

Step 3: 4-(5-Nitropyridin-2-yl)-N-(2-fluorophenyl)piperazine-l-carboxamide (B-4)To compound B-3 (6.6 g, 32 mmol) dissolved in dry THF (200 mL) was added triethylamine (8.8 mL, 63 mmol) and 2-fluorophenyl isocyanate (4.3 mL, 38 mmol). The resulting reaction mixture was heated at 80 C for 16 h then cooled to RT and concentrated. Water (150 mL) was added, and the aqueous solution was extracted with CH2CI2. The combined organic extract was dried (MgS04), filtered, and concentrated to give a yellow solid. The solid was triturated with water, filtered, and dried to give the product 4-(5-nitropyridin-2-yl)-N-(2- fluorophenyl)piperazine-l-carboxamide (B-4) as a yellow solid (11.4 g, 100% yield). MS (M+1): 346.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,82205-58-1, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); A1;,
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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. 881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Dimethyl pyridine-2,5-dicarboxylate

To a mixture of dimethyl pyridine-2,5-dicarboxylate (3.08 g, 15.78 mmol) and calcium chloride (7.01 g, 63.1 mmol) in tetrahydrofuran (33 mL) and EtOH (67 mL) was added sodium borohydride (1 .493 g, 39.5 mmol) in portions at 0 C. The reaction mixture was stirred at 0 C for 12 hrs. The mixture was poured into ice/water, was diluted with dichloromethane (400 ml.) and stirred vigorously for 15 minutes. The separated organic layer was dried over magnesium sulfate, filtered off and concentrated under reduced pressure providing methyl 6-(hydroxymethyl)nicotinate (1 .2 g) as an off white solid, which was directly used in the next step without further purification. LCMS (m/z): 168.0 [M+H]+; Rt = 0.26 min

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, 881-86-7, Dimethyl pyridine-2,5-dicarboxylate.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (2012); A1;,
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Reference of 82671-06-5 , The common heterocyclic compound, 82671-06-5, name is 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid, molecular formula is C6H2Cl2FNO2, 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.

Intermediate[00144] The overall synthetic scheme for the synthesis of5-fluoro-lH-pyrazolo [3, 4-b] pyridin-3-amine 5 is depicted below.1 6 3Reagents and conditions: i. Pd (OAc) 2, PPh3, Et3N, H2CO2; ii. 1) (COCl)2, CH2Cl2, cat. DMF; 2) NH3 (g) , dioxane, iii. TFAA, Et3N, CH2Cl2, 0C; iv. H2NNH2. H2O, n-butanol, reflux2-Chloro-5-fluoronicotinic acid (6)[00145] To a round-bottomed flask under a N2 atmosphere were added degassed DMF (270 ?iL) , 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 500C. The reaction was followed by analysis (IH NMR) of a worked- up aliquot. When all starting material was consumed (24 h) , the mixture was cooled to 00C 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 (2x) . HCl(12 N) was added slowly to pH 1 and the solution was saturated with NaCl. The mixture was extracted with EtOAc (3x) . 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-de, 300 MHz): delta 8.16 (dd, IH); 8.58 (d, IH).

The synthetic route of 82671-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/112646; (2008); 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 875781-15-0, name is 5-Bromo-2-fluoronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H3BrFNO

[00434] 1A. (R,E)-N-((5-Bromo-2-fluoropyridin-3-yl)methylene)-2-methylpropane-2- sulfmamide: To the solution of 5-bromo-2-fluoronicotinaldehyde (5 g, 24.51 mmol), titanium (IV) ethoxide (15.42 ml, 73.5 mmol) in DCM (49.0 ml) was added (R)-2- methylpropane-2-sulfinamide (3.12 g, 25.7 mmol) and the reaction mixture was stirred at rt. After 48 h, the reaction mixture was poured into brine while rapidly stirring to form a suspension. The resulting suspension was filtered through a plug of CELITE, and the filter cake was washed several times with DCM. The filtrate phases were separated, and the organic phase was washed with brine and dried over MgS04. The organic layers were then concentrated to give 7.6 g crude product which was further purified using silica gel chromatography to yield the desired product (6.97 g, 93%) as an off white solid. MS(ESI) m/z: 330.8 (M+Na)+.

With the rapid development of chemical substances, we look forward to future research findings about 875781-15-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
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Electric Literature of 73290-22-9, 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.73290-22-9, name is 2-Bromo-5-iodopyridine, molecular formula is C5H3BrIN, molecular weight is 283.89, as common compound, the synthetic route is as follows.

General procedure: Step 1: 1-(6-Bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one [0137]2-bromo-5-iodopyridine (1.0 g, 3.52 mmol), 4,4-dimethyl-imidazolidin-2-one (CAS 24572-33-6) (400 mg, 3.52 mmol, 1.0 equiv.), cesium carbonate (1.72 g, 5.28 mmol, 1.5 equiv.), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (82 mg, 0.141 mmol, 0.04 equiv.) in 10 ml of toluene was added under argon atmosphere tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (Pd2 (dba)3*CHCl3) (73 mg, 0.07 mmol, 0.02 equiv.). The mixture was stirred for 1 hour at 100 C. The mixture was directly loaded on a 50 g silicagel column and was eluted with an heptan:ethyl acetate gradient 100:0 to 0:100 and an ethyl acetate:methanol gradient 100:0 to 80:20. The desired 1-(6-bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one (810 mg, 85% yield) was obtained as a light yellow solid, MS: m/e=207.1/272.1 (M+H+).

The chemical industry reduces the impact on the environment during synthesis 73290-22-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoffmann-La Roche Inc.; Jaeschke, Georg; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2013/90332; (2013); 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. 1513-66-2, name is 2,3-Difluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3F2N

12.8 g of 2-chloro-3-aminopyridine was suspended in 120 mL of 60% aqueous hexafluorophosphoric acid, and 9.0 g sodium nitrite was added little by little thereto at 0C to precipitate crystals. The crystals were collected by filtration and washed with diethyl ether to give 15.75 g diazonium salt. Subsequently, the diazonium salt was suspended in 100 mL xylene and heated at 85C for 3 hours, 28 mL triethylamine was added thereto, and the reaction mixture was diluted with an aqueous saturated sodium bicarbonatesolution and then extracted with ethyl acetate. The extract was washed with brine, and the organic layer was dried over anhydrous sodium sulfate and then filtered through silica gel. The ethyl acetate was removed, and to the resulting xylene solution was added 6.0 mL 2-aminoethanol, and the mixture was heated at 130C for 10 hours. Then, the same procedure as in Production Example 231 was carried out, whereby 385 mg of the title compound (yellowoil) was obtained as a mixture.1H-NMR (CDCl3) delta: 3.60-3.68(m, 2H), 3.84(t, J=4.8Hz, 2H), 6.52-6.60(m, 1H), 7.12-7.20(m, 1H), 7.80-7.85(m, 1H)

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, 1513-66-2, 2,3-Difluoropyridine.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15471-17-7, 3-(Pyridin-1-ium-1-yl)propane-1-sulfonate, 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, 15471-17-7, blongs to pyridine-derivatives compound. HPLC of Formula: C8H11NO3S

General procedure: Toa mixture of toluene (30 mL) and 1,3-propane sulfone (0.10 mol, 12.2 g) in a 100 mLround bottomed flask was added pyridine (0.11 mol, 8.7 g, 8.9 mL). The reactionmixture was stirred for 24 h at 50 oC under a nitrogen atmosphereuntil a white precipitate (PyPS) was formed. After filtration, washing withdiethyl ether and drying in a vacuum, PyPS was obtained. To an aqueous solutionof H3PW12O40 (0.03 mol, 86.4 g) was added PyPS(0.09 mol, 18.1 g) and then the mixture was stirred at room temperature for 24h. Finally, the solution was removed in vacuum to give the product [PyPS]3PW12O40as a solid. Thus [MIMPS]3PW12O40, [MIMPS]3PMo12O40,[PyPS]3PMo12O40, [TEAPS]3PW12O40and [TEAPS]3PMo12O40 were prepared usingaccording starting materials.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15471-17-7, its application will become more common.

Reference:
Article; Fu, Renzhong; Yang, Yang; Ma, Yunsheng; Yang, Fei; Li, Jingjing; Chai, Wen; Wang, Quan; Yuan, Rongxin; Tetrahedron Letters; vol. 56; 30; (2015); p. 4527 – 4531;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 624-28-2 ,Some common heterocyclic compound, 624-28-2, molecular formula is C5H3Br2N, 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: Procedure (take intermediate 3a as an example): 2,5-dibromopyridine (61.5 mmol), phenol (64.6 mmol), cuprous iodide (6.15 mmol), and Cs2CO3 (92 mmol) were placed in a 250 mL dried flask. Add 150 mL DMSO, then add TMEDA (6.15 mmol), heated to 110 degrees under Ar protection (Unless otherwise specified, the temperature in the present invention is in degrees Celsius C), react for about 20 hours, TLC conversion complete. After cooling to room temperature, a large amount of ethyl acetate was added, the mixture was washed 4 times with water and extracted twice with ethyl acetate. The combined EA (ethyl acetate) phase was washed with brine, and the organic layer was dried, filtered and evaporated to dryness to give the product as a brown oil.

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. 624-28-2, 2,5-Dibromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou He Zheng Pharmaceutical Co., Ltd.; Zhou Xinglu; Liu Xingguo; Luo Wenhua; Zhong Shichun; Huang Jinglai; Dong Xiaowu; Huang Wenhai; Hu Miao; (55 pag.)CN108069974; (2018); A;,
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Pyridine | C5H5N – PubChem

Reference of 67625-37-0, 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.67625-37-0, name is Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate, molecular formula is C10H9BrN2O2, molecular weight is 269.0947, as common compound, the synthetic route is as follows.

A stirred solution of ethyl 6-bromoimidazo[l,2-a]pyridine-2-carboxylate(1-6, 4.0 g, 14.86 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (A17, 6.42 g, 25.27 mmol) and KOAc(2.47 gm, 25.27 mmol) in dioxane(100 mL) was degassed with argon for 30 minutes. Then[I,G- Bis(diphenylphosphino)ferrocene]palladium(II) dichloride(0.761 g, 1.04 mmol) was added. The reaction mixture was heated at 90C for 16 h. After completion, reaction mixture quenched with water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude. This crude washed with 30% diethyl ether in hexane and concentrated the filtrate to offered ethyl 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)imidazo[l,2-a]pyridine-2-carboxylate 1-27 as brown gummy liquid. Yield: 7.8 g LC-MS(ES) m/z = 235.09[M+H]+.

The chemical industry reduces the impact on the environment during synthesis 67625-37-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem