Day: January 18, 2021

Application of 1124382-72-4, 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. 1124382-72-4, name is 2-Amino-8-bromo[1,2,4]triazolo[1,5-a]pyridine, molecular formula is C6H5BrN4, 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.

To a solution of the 2-amino-triazolopyridine (3) (7.10 g, 33.3 mmol) in dry CH3CN (150 mL) at 5C is added Et3N (11.6 mL, 83.3 mmol) followed by the appropriate acid chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material (3) is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and acid chloride (33 3 mmol) may be added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp, (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids may be collected by filtration, washed with H2O (2×50 mL), acetone (50 mL) and Et2O (50 mL), then dried in vacuo to give the required intermediate (4). In some cases column chromatography (petrol/EtOAc) may be required to obtain pure compounds.

According to the analysis of related databases, 1124382-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; JOUANNIGOT, Nolwenn; BLANC, Javier; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10186; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1065267-14-2 ,Some common heterocyclic compound, 1065267-14-2, molecular formula is C6H5F2NO, 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 stirred solution of 3,5-difluoropyridin-2-yl)methanol (Intermediate 30, 1.7g, 11.72mmol) in DCM (10OmL) was added Dess-Martin periodinane (DMP) (8.45g, 19.92mmol). The resulting solution was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was diluted with DCM, and washed with saturated NaHCU3 (2x), H2O and brine. The organic layer was dried over Na2SO4, and concentrated. Purification by column chromatography (EtOAc:Hexane = 2:8) provided the title compound (1.4g, 80%) as a thick oil. LCMS: [M+H]+144

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1065267-14-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/117050; (2008); 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. 13535-01-8, name is 5-Bromopyridin-3-amine, molecular formula is C5H5BrN2, 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. Safety of 5-Bromopyridin-3-amine

Intermediate 4Preparation of lambda/-(5-bromo-3-pyridinyl)-2,4-difluorobenzenesulfonamide To a cold (0 0C) stirred solution of 3-amino-5-bromopyridine (18.6 g, 107.4 mMol) in dry pyridine (100 mL) was added 2,4-difluorobenzenesulfonyl chloride (25 g, 112.8 mMol) over 3 minutes. The reaction mixture was stirred at 0 0C for 1 h and evaporated to dryness under vacuum. The residue was diluted with H2O (400 mL) and EtOAc (400 mL). The organic layer was washed with H2O and brine, and the combined aqueous layers were extracted with EtOAc (100 mL). The combined extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was dissolved in boiling EtOAc (200 mL), and placed in a freezer for 2 days. Two crops were obtained through filtration, which were combined and triturated with boiling 35% EtOAc in hexanes. After cooling to room temperature, the precipitate was collected by filtration and dried to constant weight to provide 27.2 g of iV-(5-bromo-3-pyridinyl)-2,4- difluorobenzenesulfonamide as a light orange solid. MS (ES) m/e 351.0 (M + H)+.

With the rapid development of chemical substances, we look forward to future research findings about 13535-01-8.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157191; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56622-54-9 , The common heterocyclic compound, 56622-54-9, name is (6-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, 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 5 mL microwave vial was charged with l-bromo-3-iodo-5-(trifluoromethoxy)benzene(98 mg, 0.27 mmol), (6-methylpyridin-3-yl)methanamine (50 mg, 0.41 mmol), molybdenum hexacarbonyl (160 mg, 0.61 mmol), palladium acetate (8 mg, 0.036 mmol), l,8-diazabicyclo[5.4.0]undec- 7-ene (120 mg, 0.79 mmol), and 1,4-dioxane (2 mL). The vial was sealed under nitrogen and the reaction was subjected to microwave irradiation at 120 0C for 20 minutes. After cooling, the mixture was purified via flash chromatography to afford the desired product as a white solid. LC-MS: 391.2 [M+l]+; 1H NMR (CDCl3, 400 MHz): 8.43 (d, J = 2.1 Hz, IH), 7.85 (t, J = 1.5 Hz, IH), 7.63-7.61 (m, 2H), 7.52 (s, IH), 7.16 (d, J = 8.0 Hz, IH), 6.74 (br, IH), 4.60 (d, J = 5.8 Hz, 2H), 2.55 (s, 3H).

The synthetic route of 56622-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7598-35-8, 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. 7598-35-8, name is 2-Bromopyridin-4-amine. A new synthetic method of this compound is introduced below.

To a cooled (0 C.) solution of 2-bromo-4-aminopyridine (295 mg, 1.5 mmol) in dry DMF (5 ml) was added NaH (120 mg, 3.0 mmol, 60% dispersion in mineral oil) carefully. The mixture was stirred at room temperature for 30 min and then cooled to 0 C. again. A solution of the acid chloride from the preceeding step in dry DMF (5 ml) was added into the mixture slowly. The resulting mixture was stirred for an additional hour at room temperature and then quenched with ice-water (20 ml). The mixture was extracted with ethyl acetate (3¡Á50 ml). The combined organic extracts were washed with brine (20 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (ethyl acetate/petroleum ether=1:10) to give N-(2-bromopyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (389 mg, 70% yield). LCMS (ESI) m/z: 369.9 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7598-35-8, 2-Bromopyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; US2010/317643; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86604-79-7 ,Some common heterocyclic compound, 86604-79-7, molecular formula is C8H10N2O3, 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.

Step 4; [00286] Jifj-2,3,5-Dimethyl-4-nitropyridine-l -oxide: A dry heavy-walled teflon screw cap glass tube equipped with a magnetic stirrer was charged with 2,3,5-trimethyl-4- nitropyridine-1 -oxide (5 g, 27.5 mmol), potassium carbonate (3.8 g, 27.5 mmol) and deuterium oxide (30 mL) under nitrogen. The apparatus was sealed and the mixture was placed in an oil bath at about 15O0C for about 2 hours. The reaction was cooled to ambient temperature, and sodium chloride (1Og) and brine (50 mL) were added. The title product, 4.2 g of a yellow solid with identical TLC behavior as the starting material (Rf = 0.3 in 10% methanol-DCM), was isolated using standard extractive work up. The above process was repeated to afford 3.25 g of product that had deuterium incorporation of 98.1% as determined by GC-MS analysis. Yield: 65%. GC-MS: [M]+: 192 (81.6%, 2,3,5-trimethyl-4- nitropyridine-1 -oxide-dio), 191 (18.3%, 2,3,5-trimethyl-4-nitropyridine-l-oxide-d9). Step 4[00294] fi(m-2,3,5-Dimethyl-4-nitropyridine-1 -oxide: The title compound was made by following the procedure set forth in Example 1, step 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,86604-79-7, its application will become more common.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; WO2008/127640; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5654-95-5, 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 5654-95-5, name is 1H-Pyrrolo[2,3-b]pyridine-2,3-dione. This compound has unique chemical properties. The synthetic route is as follows.

Method 1: Under argon atmosphere at 90 C, a solution of thallium(III) acetate (1.91 g, 5 mmol) in glacial acetic acid (25 mL) was added dropwise within 2 h to a solution of 1 (1.075 g, 9.1 mmol) in glacial acetic acid (7.5 mL). The mixture was stirred overnight at 90 C, cooled with ice and the solvent was removed by evaporation. The residue was extracted with ethyl acetate, filtered and the product was purified by repeated crystallization from ethyl acetate (red violet crystals, yield: 130 mg, 10.9%).Method 2: Acid condensation. 7-Azaisatin (67.1 mg, 0.45 mmol) and 7-azaindoxyl-3-acetate (70 mg, 0.4 mmol) were suspended under argon atmosphere in acetic acid (4 mL) and conc. HCl (340 muL). The mixture was stirred at room temperature for overnight and diluted with water (30 ml). The precipitate was filtrated and purified by recrystallization from 1 N HCl/EtOH (75 mg, 0.28 mmol, 62.2%).1H NMR (400 MHz, DMSO-d6, delta = 2.49 ppm): 11.58 (s, 1H), 10,74 (s, 1H), 8.84 (dd, 1H, 3JH,H = 7.9 Hz, 4JH,H = 1.7 Hz), 8.50 (dd, 1H, 3JH,H = 4.8 Hz, 4JH,H = 1.7 Hz), 8.15-8.11 (m, 2H), 7.15-7.07 (m, 2H). 13C-{1H} NMR (150 MHz, DMSO-d6, delta = 39.5 ppm): 186.3, 170.5, 163.4, 155.8, 155.4, 147.8, 138.7, 133.8, 131.5, 118.2, 117.9, 115.5, 112.9, 105.7. C14H8N4O2¡¤0.67 H2O. Found: C 60.89, H 3.35, N 19.85; requires: C 60.87, H 3.41, N 20.28.

According to the analysis of related databases, 5654-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cheng, Xinlai; Merz, Karl-Heinz; Vatter, Sandra; Christ, Jochen; Woelfl, Stefan; Eisenbrand, Gerhard; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 247 – 255;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 882033-66-1, 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. 882033-66-1, name is 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4ClFN2, 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.

Example 222A mixture of 4-chloro-5-fluoro-lH-pyrrolo [2, 3-b] pyridine (30 mg) and cyclohexylamine (87 mg) in DMI(O.4 mL) was heated in the microwave reactor (2000C, 4 hours) . The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (10 mL) and half-saturated aqueous sodiumhydrogencarbonate (1OmL) . The aqueous phase was extracted with EtOAc (2x 10 mL) and combined organic layers were washed with brine (20 mL) , dried over MgSO4, and concentrated. Purification of the crude product by preparative silica gel thin-layer chromatography (EtOAc) gave N-cyclohexyl-5-fluoro- lH-pyrrolo [2, 3-b]pyridin-4-amine (5 mg) as a yellow solid. 1H-NMR (CDCl3) delta: 9.90 (IH,br) , 7.95 (IH, d, J=4.4Hz) , 7.14 (IH, d, J=3.4Hz) ,6.50(lH,d,J=3.4Hz),4.46(lH,br) , 3.90-3.80 (IH,m) ,2.2-1.2 (1OH,m) . MS(ESI) :m/z 234(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 882033-66-1, 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14254-57-0, 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. 14254-57-0, name is Isonicotinoyl chloride, molecular formula is C6H4ClNO, 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.

Example 1Synthesis of(3-chloro-4-methoxyphenyJ)-(2-pyridin-4-ylquinolin-4-yl) amine (E 1) Step (i): Synthesis ofN-(2~acetylphenyl) isonicotinamide (1); To a mixture of orthoaminoacetophenone (2.0 grams, 14.8 mmol) and triethylamine (7.2 mL, 52.0 mmol) in dry tetrahydrofuran (15 niL) was added EPO dropwise to a freshly prepared isonicotinyl chloride (2.5 grams, 17.8 mmol) dissolved in 50 mL of tetrahydrofuran, while the mixture was stirred under a nitrogen atmosphere at 0 0C. After this mixture was stirred at 0 0C for 2 hours, the reaction mixture was allowed to warm to room temperature, and stirred overnight. The resulting mixture was poured into ice-cold water and partitioned in ethyl acetate (2 x 250 mL). The organic layers were collected and washed with water (100 mL) followed by saturated sodium chloride (125 mL) solution, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue thus obtained was purified by column chromatography using ethyl acetate and petroleum ether, followed by washing with diethyl ether to afford the desired product (1) as a pink colored solid (0.975 gram); Yield: 28%.1H NMR (CDCl3, 200 MHz):delta 12.89 (br s, D2O exchangeable, NH), 8.94 (d, J = 8.4 Hz, IH), 8.83 (d, J = 5.6 Hz, 2H), 7.99 (d, J = 7.8 Hz, IH), 7.90 (d, J = 5.9 Hz, 2H), 7.65 (t, J – 8.1 Hz, IH), 7.20 (d, J = 7.6 Hz, IH), 2.74 (s, 3H). IR (KBr, cm”1): 3439.7, 1675.0, 1644.4, 1522.5, 1249.0, 757.5. MS: (CI) m/z: 241 (M++l).

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 14254-57-0, Isonicotinoyl chloride.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; PAL, Manojit; KHANNA, Ish; SUBRAMANIAN, Venkataraman; PADAKANTI, Srinivas; PILLARISETTI, Sivaram; WO2006/58201; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 113682-56-7, Adding some certain compound to certain chemical reactions, such as: 113682-56-7, name is 1,4-Di(pyridin-4-yl)benzene,molecular formula is C16H12N2, 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 113682-56-7.

General procedure: Under an N2 atmosphere, a mixture of the imidazolium salt (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride, 2.2 mmol), the required N-heterocycle (1.0 mmol), PdCl2(2.2 mmol) and K2CO3(2.2 mmol) was stirred in anhydrous THF (10 mL) under reflux for 12 h. After cooling, filtration and evaporation, the residue was purified by preparative TLC on silica gel plates, eluting with CH2Cl2 to afford the corresponding dinuclear N-heterocyclic carbene-palladium(II) complexes 1-4.

According to the analysis of related databases, 113682-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Tao; Xu, Kai; Wang, Wanli; Zhang, Anan; Liu, Lantao; Transition Metal Chemistry; vol. 43; 4; (2018); p. 347 – 353;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem