Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, 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 N-(6-Chloropyridin-2-yl)pivalamide, blongs to pyridine-derivatives compound. Application In Synthesis of N-(6-Chloropyridin-2-yl)pivalamide

Step 2: Synthesis of N-(6-chloro-3-iodopyridin-2-yl)-2,2-dimethylpropionamideTo a solution of N-(6-chloropyridin-2-yl)-2,2-dimethylpropionamide (20 g, 94 mmol) in dry THF (500 mL) at -78 C, 1.3 M t-BuLi in hexane (220 mL, 282 mmol) is added dropwise. The reaction mixture is stirred for 30 min and a solution of iodine (29 g, 114 mmol) in dry THF is added. The reaction mixture is stirred for 3 h at -78 C then is warmed to ambient temperature and stirred for another 1 h. The reaction mixture is quenched with IN HC1 and is extracted with ethyl acetate (2 x 250 mL). The organic layers are separated and washed with Na2S203 solution and saturated NaHC03 solution, respectively. The combined organic layers are dried (Na2S04) and evaporated under reduced pressure. The crude residue is purified by flash column chromatography using 20% EtO Ac/petroleum ether to afford the title compound as a pale yellow solid (15 g, 49%).

The synthetic route of 86847-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; BURKE, Jennifer; GUO, Xin; KIRRANE JR., Thomas, Martin; SNOW, Roger, John; ZHANG, Yunlong; WO2011/71725; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 893444-21-8, 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 893444-21-8, name is 3-Nitro-6-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To a solution of 3-nitro-6-(trifLuoromethyl)pyridin-2-amine (838mg, 4.05mmol) in methanol (30mL) was added 10% palladium on carbon (400mg). The mixture was hydrogenated on a Parr shaker at 40 psi for 90 min. The catalyst was filtered and the solvent was evaporated to give 6~(trifluoromethyl)pyridine-2,3-diamine as a yellow solid. LC-MS (M+H) = 178

According to the analysis of related databases, 893444-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SCHERING CORPORATION; SPERBECK, Donald, M.; DEVITA, Robert, J.; BALKOVEC, James, M.; GREENLEE, Mark, L.; WU, Zhicai; YU, Yang; VACHAL, Petr; ZHOU, Gang; WU, Heping; KUANG, Rongze; TING, Pauline; ASLANIAN, Robert; WO2012/64569; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 65147-89-9, 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. 65147-89-9, name is 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine. A new synthetic method of this compound is introduced below.

Example 238 Under an argon stream, a mixture of 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine (Compound of Reference Example 3) (90 mg), 2- (tributylstanyl) furan (305 mg), dichlorobis(triphenylphosphine)palladium(II) (23 mg) and N,N-dimethyl formamide (4 ml) was stirred at 80C for 24 hours.. The reaction mixture was poured into water and extracted with ethyl acetate – tetrahydrofuran (3: 1, v/v).. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure.. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate – chloroform – hexane (1: 1: 4, v/v) were concentrated under reduced pressure.. The resulting crystals were collected by filtration to obtain 6-(2-furyl)-2-phenyl-1H-imidazo[4,5-b]pyridine (49 mg, 57 %). HPLC (220 nm) Purity 100 % (Retention time 2.66 minutes) MS (APCI+, m/e) 262 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65147-89-9, 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1460067; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 84539-34-4, Adding some certain compound to certain chemical reactions, such as: 84539-34-4, name is 4-Amino-3,5-dibromopyridine,molecular formula is C5H4Br2N2, 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 84539-34-4.

To a cooled (0 C) solution of 4-amino-3,5-dibromopyridine 12 (2.0 g, 7.94 mmol, 1.0 equiv) in 48% HBF4 aq (30 mL) was added dropwise NaNO2 (5.4 g, 79.4 mmol, 10 equiv) in water (16 mL) ensuring that no gas evolution could be detected. The resultant slurry was stirred at 0 C for 30 min. The reaction mixture was filtered to afford a white solid. The solid was quickly transferred portionwise to a stirred solution of KI (2.1 g, 12.7 mmol, 1.6 equiv) in 25 mL of acetone/H2O (2/3). The resultant brown slurry was decolorized with saturated Na2S2O3 and carefully neutralized with NaHCO3. The solution was then extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification by silica gel column chromatography (hexane/EtOAc = 10/1) yielded 5 (1.59 g, 4.38 mmol, 55%) as a colorless solid; Rf 0.61 (hexane/EtOAc = 5/1); mp 186-190 C; IR (KBr, cm-1) 1858, 1808, 1634, 1547, 1522, 1496, 1404, 1389, 1205, 1175, 1096, 1020, 883, 756, 687, 517, 422; 1H NMR (300 MHz, CDCl3) delta 8.56 (2H, s, H2/6); 1H NMR (300 MHz, DMSO-d6) delta 8.65 (2H, s, H2/6); 13C NMR (CDCl3, 75 MHz) delta 148.4, 129.9, 120.3; 13C NMR (75 MHz, DMSO-d6) delta 148.3, 129.4, 122.1; EI-MS (m/z) Calcd for C5H2Br2IN [M]+ 360.76. Found 360.75; EI-HRMS (m/z) Calcd for C5H2Br2IN [M]+ 360.7599. Found 360.7589.

According to the analysis of related databases, 84539-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Murakami, Yuko; Yanuma, Hiroto; Usuki, Toyonobu; Tetrahedron Asymmetry; vol. 23; 22-23; (2012); p. 1557 – 1563;,
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 24207-22-5, name is 2-Bromo-3-methoxy-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 24207-22-5

To a solution of 2-bromo-3-methoxy-6-methylpyridine (2c) (310 g, 1.53 mol) in 6000 mL of water at 60 C was added KMnO, (725 g, 4.59 mol) in small portions over a 90 min period with vigorous mechanical stirring. A dark purple solution resulted. This solution was kept at 90 C for a further 3 h and filtered through Celite while still hot to give a colourless filtrate. After cooling, the aqueous solution was acidified to pH 1-2 by adding 6 N HCI. The white solid obtained was collected by filtration to give on drying 6-bromo-5-methoxy-2- pyridinecarboxylic acid (2d) (302g, 85%) of product, which was used as such in the next reaction without further purification. An analytical sample was obtained by recrystallization from methanol to give 6-bromo-5-methoxy-2-pyridinecarboxylic acid; 1H NMR (300 MHz, DMSO-tfe) delta 7.40 – 7.28 (m, 1H), 7.17 (d, J = 8.3 Hz, 1 H), 3.83 (d, J = 1.7 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 24207-22-5.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda S.; KAMATH, Vivekanand P.; GOWAN, Walter; (222 pag.)WO2016/29214; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1018505-59-3 ,Some common heterocyclic compound, 1018505-59-3, molecular formula is C11H18N4, 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-(2-Dimethylcarbonyl-2-carbonyl-ethylamino)-2-pyrimidinecarboxylic acid (1.26 g, 1.2 eq),5-(4-Ethyl-piperazin-1-yl)-piperidin-2-amino (0.81 g, 1 eq)And triethylamine (500 muL) in DMF (15 mL),Then HBTU (1.51 g, 1.5 eq) was added. The mixture was stirred at room temperature for 16 hours.Then with EtOAc (50 mL)And saturated NaHCO3 solution(15 mL), the layers were separated and EtOAc EtOAcThe combined organic layers were dried (MgSO4), filtered and evaporated.The residue was purified by column chromatography.1.04 g of the title compound 6 was obtained as a white solid(yield: 47%),Its nuclear magnetic resonance spectrum data is as follows:

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. 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Hu Xiande; Zhou Liming; Sui Guilan; (22 pag.)CN109568256; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1256823-07-0, Adding some certain compound to certain chemical reactions, such as: 1256823-07-0, name is 5-Bromo-4-methoxypicolinonitrile,molecular formula is C7H5BrN2O, 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 1256823-07-0.

To a stirred solution of 4-methyl-1H-imidazole (580 mg, 7.04 mmol) in acetonitrile (24 mL) under an argon atmosphere were added potassium carbonate (1.3 g, 9.38 mmol) and 18-crown-6 (2.47 g, 9.38 mmol) at room temperature. The reaction mixture was stirred at 60 oC for 2 h. Then 5-bromo-4-methoxypicolinonitrile (1 g, 4.69 mmol) was added to the reaction mixture at room temperature. The reaction mixture was stirred at reflux for 18 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 90% EtOAc:hexanes to afford 4- methoxy-5-(4-methyl-1H-imidazol-1-yl) picolinonitrile (250 mg, 25%) as a yellow solid. 1H- NMR (CDCl3, 500 MHz): delta 8.58 (s, 1H), 7.82 (s, 1H), 7.39 (s, 1H), 6.99 (s, 1H), 401 (s, 3H), 2.23 (s, 3H); LCMS: 215 (M+1); (column; X-Bridge C-18 (50 × 3.0 mm, 3.5 mum); RT 2.45 min. 0.05% Aq TFA: ACN; 0.8 mL/min); TLC: EtOAc (Rf: 0.2).

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. 1256823-07-0, 5-Bromo-4-methoxypicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1018505-59-3 ,Some common heterocyclic compound, 1018505-59-3, molecular formula is C11H18N4, 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 3-chloro-7-(3, 5-dimethoxyphenyl) isoqinoline (50 mg, 0.167 mmol) , 5-(4- ethylpiprazine-l-yl) pyridine-2-amine (38 mg , 0.183 mmol), X-Phos ( 8 mg, 10 mol% ) and cesium carbonate (108.4 mg, 0.334 mmol) in Toluene (4 mL) and t-BuOH (1 mL) (4: 1) argon was purged for 20 min. Then was added Pd(OAc)2 (3.76 mg, 10 mol%) again argon was purged for 5 min. The reaction mixture was heated at 120C for O/N. The reaction mixture was cooled to room temperature and filtered through celite pad and filtrate was concentrated under reduced pressure. Product was purified by column chromatography on silica gel column using DCM: MeOH: NH3 aq. (94:6: 1%) as an eluent to afford 7-(3,5-dimethoxyphenyl)-N-[5- (4-ethylpiperazin-l-yl)pyridin-2-yl]isoquinolin-3 -amine (20 mg) as a brown solid. 1H NMR (400 MHz, CDC13) delta 9.00 (s, 1H), 8.14 (s, 1H), 8.06 (d, J = 2.5 Hz, 1H), 8.00 (s, 1H), 7.79 (dd, J = 19.3, 8.6 Hz, 2H), 7.42 (s, 1H), 7.31 (dd, J = 8.9, 2.7 Hz, 1H), 7.10 (d, J = 8.9 Hz, 1H), 6.83 (d, J = 1.9 Hz, 2H), 6.49 (s, 1H), 3.88 (s, 6H), 3.25 – 3.14 (m, 4H), 2.66 (d, J = 4.4 Hz, 4H), 2.50 (q, J = 7.1 Hz, 2H), 1.15 (t, J = 7.2 Hz, 3H).M/Z: 469.58, M+l : 470.4, tR= 2.1 min. (System 2)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018505-59-3, its application will become more common.

Reference:
Patent; EVOTEC (UK) LTD.; MC CARTHY, Clive; MILLS, Matthew; WO2014/44846; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 107351-82-6, 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 107351-82-6, name is 2-Bromo-5-phenylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 3 Synthesis of 2-[4-(5-phenylpyridin-2-yl)phenyl]-4,6-di-m-tolyl-1,3,5-triazine Under a stream of argon, 3.0 ml of a hexane solution containing 4.2 mmol of butyl lithium was slowly added to 80 ml of tetrahydrofuran cooled to -78C in which 1.58 g of 2-(4-bromophenyl)-4,6-di-m-tolyl-1,3,5-triazine obtained in Reference Example 2 had been dissolved. After stirring at -78C for 15 minutes, 0.87 g of trimethyltin chloride was added thereto and stirred at -78C for 45 minutes and then at room temperature for 30 minutes. After evaporating and drying tetrahydrofuran under a reduced pressure, 120 ml of toluene in which 1.07 g of 2-bromo-5-phenylpyridine had been dissolved and 0.44 g of tetrakis(triphenylphosphine)palladium(0) were added to the thus obtained solid and stirred under heating reflux for 3 days. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was recrystallized from dichloromethane-methanol. The thus obtained crude product was purified by a silica gel column chromatography (eluding solution hexane:chloroform = 3:2 to 1:1) and then again recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2-[4-(5-phenylpyridin-2-yl)phenyl]-4,6-di-m-tolyl-1,3,5-triazine (0.14 g, yield 8%). Its melting point is shown in Table 4. Distinct point of glass transition was not observed. 1H-NMR (CDCl3): delta 2.48 (s, 6H), 7.33-7.51 (m, 7H), 7.56-7.64 (m, 2H), 7.84-7.99 (m, 2H), 8.21 (d, J=8.5 Hz, 2H), 8.49-8.58 (m, 4H), 8.84 (d, J=8.6 Hz, 2H), 8.95 (d, J=1.7 Hz, 1H). 13C-NMR (CDCl3): delta 21.6, 120.9, 126.3, 127.0, 127.1, 128.3, 128.6, 129.2, 129.5, 133.3, 135.3, 135.6, 136.2, 136.9, 137.4, 138.3, 142.4, 148.2, 155.2, 171.2, 171.8.

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 107351-82-6, 2-Bromo-5-phenylpyridine.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH CENTER; EP1930329; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13626-17-0, Adding some certain compound to certain chemical reactions, such as: 13626-17-0, name is 3,5-Dibromo-4-chloropyridine,molecular formula is C5H2Br2ClN, 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 13626-17-0.

Compound (M-41) (10.0 g, 39.5 mmol) was suspended in acetonitrile (50 mL), DIPEA (15 mL, 87 mmol) wasadded at room temperature, phosphoryl chloride (7.4 mL, 79 mmol) was added under ice-cooling, and the mixture wasstirred with heating under reflux for 17 hr. The mixture was allowed to cool, and the reaction mixture was added dropwiseto ice water, and neutralized with sodium carbonate (11.6 g, 138 mmol). Thereafter, the mixture was extracted with ethylacetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solventwas evaporated under reduced pressure to give a chloro compound (yield 10.6 g, 99%) as a brown solid. The chlorocompound (10.6 g, 39.1 mmol) was dissolved in THF (70 mL), sodium methoxide (28% methanol solution, 14 mL, 59mmol) was added, and the mixture was stirred at 60C for 30 min. The mixture was allowed to cool, water was addedto the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successivelywith water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reducedpressure to give compound (VII-46) (yield 9.21 g, 88%) as a yellow solid

According to the analysis of related databases, 13626-17-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem