Day: April 14, 2022

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

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

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

Electric Literature of 113293-70-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 113293-70-2 as follows.

Step 1 5-(2,6-Dichloropyridin-4-yl)oxazole 528 mg of 2,6-dichloroisonicotinaldehyde (this compound was prepared by the method described in J. Chem. Soc., Chem. Commun., 1998, 1567-1568) was dissolved in 10 ml of methanol, and 586 mg of p-toluenesulfonyl methyl isocyanide and 415 mg of potassium carbonate ware added, and the mixture was stirred at 50 C. for 30 minutes. The reaction solution was concentrated, and then diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 630 mg of the objective compound as white powder. MS (ESI) m/z 215 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; NIPPON SHINYAKU CO., LTD.; US2011/288065; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

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. 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Nitro-1H-pyrazolo[3,4-b]pyridine

4N NaOH (5.12 mL, 20.5 mmol) was added to a cold (00C) solution of5-nitro-lH-pyrazolo[3,4-b]pyridine (0.84 g, 5.12 mmol) in dioxane (30 mL), followed by bromine (1.05 mL, 20.5 mmol). The cold bath was removed, and the reaction mixture was left at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and quenched with saturated aqueous Na3S3O3 (50 mL). The aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried, filtered and concentrated.The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate(9:1) to give 3 -bromo-5-nitro-l H-pyrazolo [3 ,4-b]pyridine (1.10 g, 88%) as a solid.

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, 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRADL, Stefan; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25968; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 66909-38-4, 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 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

Potassium thiocyanate (0.682 g, 7.01 mmol) was dissolved in acetic acid (10 mL) and cooled to 0 C. 6-chloro-4-methylpyridin-3-amine (1.00 g, 7.01 mmol) was dissolvedacetic acid (3.33 mL) and added dropwise. Bromine (0.361 mL, 7.01 mmol) was dissolved in acetic acid (3.33 mL) and added dropwise to the reaction mixture. The reaction mixture was allowed to warm to room temperature for 18 h. The reactionmixture was concentrated under reduced pressure. The resultant residue was diluted with water and neutralized with 1 N NaOH. The aqueous solution was extracted with EtOAc (x3). The combined organic layer was washed with brine, dried with sodium sulfate, and concentrated under reduced pressure. The reaction mixture was purified on Prep HPLC using Method A to yield Intermediate 191A (0.890 g, 4.46 mmol, 63.6 % yield) as awhite solid. ?H NMR (400MHz, CHLOROFORM-d) 7.08 (d, J0.7 Hz, 1H), 3.39 (dt, J3.2, 1.6 Hz, 2H), 2.50 (d, J0.7 Hz, 3H). LC-MS: method H, RT = 0.92 mm, MS (ESI) m/z: 200.1 (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 66909-38-4, 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 90610-06-3, Methyl 2-(6-methylpyridin-3-yl)acetate, 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, Quality Control of Methyl 2-(6-methylpyridin-3-yl)acetate, blongs to pyridine-derivatives compound. Quality Control of Methyl 2-(6-methylpyridin-3-yl)acetate

To a stirred solution of methyl (6-methylpyridin-3-yl)acetate (60 mg, 0.36 mmol) in methanol (5 ml) was added NaOH (1.0 ml of a 2M aqueous solution, 2.0 mmol) and the resulting solution was heated at 65 0C for 2 hours. The solvent was then removed at reduced pressure and the resulting residue was dissolved in methanolic HCl (5 ml) and then reconcentrated to yield the title product (54 mg, quant, yield) that was used without further purification. LCMS data: Calculated MH+ (152); Found 100% (MH+) m/z 152, Rt = 0.79 min. Method C.

The synthetic route of 90610-06-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; DAVENPORT, Adam, James; HALLETT, David, James; STIMSON, Christopher, Charles; WO2010/86403; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 18699-87-1, 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. 18699-87-1, name is 2-Methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

Example 9; Synthesis of 3-amino-1-hydroxy-3,4-dihydro-1,5-naphthyridin-2(1H)-one, dihydrochloride salt (50); 2-Methyl-3-nitropyridine 1-oxide (44); To a solution of 2-methyl-3-nitropyridine (43) (0.86 g, 6.23 mmol) in DCM (30 mL) was added mCPBA (2.8 g, 12.5 mmol). The reaction was then allowed to stir at RT for 6 h. Sodium thiosulfate (900 mg) was added and the mixture was allowed to stir overnight. The reaction mixture was diluted with additional DCM and washed with a saturated aqueous NaHCO3 solution. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (Gradient: 0% to 20% MeOH in DCM) to afford the product (782 mg, 81%). LCMS m/z 155.0 (M+1). 1H NMR (400 MHz, CDCl3) delta 2.73 (m, 3H), 7.30 (br dd, J=8.1, 6.8 Hz, 1H), 7.72 (dq, J=8.4, 0.5 Hz, 1H), 8.48 (dq, J=6.6, 0.6 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18699-87-1, 2-Methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US2010/324043; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1256789-09-9 , The common heterocyclic compound, 1256789-09-9, name is Methyl 6-chloro-2,4-dimethylnicotinate, molecular formula is C9H10ClNO2, 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) Synthesis of 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylesterTo a solution of 710 mg, (3.6 mmol) 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester in CCI4 (16 ml) were added 688 mg (3.90 mmol) N-bromosuccinimide, 59 mg (0.36 mmol) AIBN and 210 muIota (3.72 mmol) acetic acid . The reaction mixture was irradiated with a 200W Wolfram lamp at 60 C for 24 h. The mixture was then filtered through celite, washed with CCI4 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue a mixture of 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester, 4-(bromomethyl)-6- chloro-2-methyl-pyridine-3-carboxylic acid methylester and 2-(bromomethyl)-6-chloro-4- methyl-pyridine-3-carboxylic acid methylester was obtained. This mixture was dissolved in dioxane (10 ml) and added at 0 C to a solution prepared by dissolving 594 mg (25.8 mmol) sodium in MeOH (11 ml) at 0 C. This reaction mixture was stirred at RT for 3 h. Then the reaction solution was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue again a mixture of 6-chloro-4-(methoxymethyl)-2-methyl- pyridine-3-carboxylic acid methylester and 6-chloro-2-(methoxymethyl)-4-methyl-pyridine-3- carboxylic acid methylester was obtained. This material was dissolved in NMP (7.8 ml) and 860 muIota (9.85 mmol) morpholine and 1.36 g (9.85 mmol) K2C03 were added followed by heating at 100 C for 5 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 90 mg (0.32 mmol, 9%) 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylester.

The synthetic route of 1256789-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem