Month: April 2022

Electric Literature of 98121-41-6, 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 98121-41-6, name is 3-Amino-5,6-dichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 2D 5-bromo-2,3-dichloropyridine A 5 L flask with mechanical stirrer, thermocouple, and addition funnel was charged with the product of Example 2C (70 g, 429 mmol) and 48% HBraq (240 mL). The suspension was maintained at 0-5 C. as a solution of NaNO2 (32.0 g, 464 mmol) in water (100 mL) was added dropwise over 1 hour. Additional water (200 mL) was added and the mixture was stirred for 10 minutes at 0-5 C. The mixture was treated with CuBr (32.6 g, 227 mmol) in portions over 20 minutes followed by additional water to maintain a fluid reaction mixture. The mixture was allowed to warm to room temperature and diluted with water. The mixture was distilled at ambient pressure, until the distillate ran clear (1.5 L collected). The distillate was extracted with EtOAc (3*500 mL) and the combined extracts were washed with brine (100 mL), dried (MgSO4), and concentrated to provide 5-bromo-2,3-dichloropyridine as a solid. 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, J=3 Hz, 1H), 8.38 (d, J=3 Hz, 1H).

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 98121-41-6, 3-Amino-5,6-dichloropyridine.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2005/261348; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 67367-24-2, name is Methyl 4-hydroxynicotinate, the common compound, a new synthetic route is introduced below. Product Details of 67367-24-2

A solution of the required alcohol (0.30 mmol; 3 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is either treated with silica gel-supported sulfonic acid (5.0 eq.; Silicycle SiliaBond Tosic Acid; SCX; R60530B; 0.8 mmol/g), shaken 1 h at rt and filtered, or loaded on a corresponding cartridge (Silicycle SiliaPrep Tosic Acid Si-SCX). In both cases, the resin is then washed with DCM, 1 : 1 DCM/MeOH and MeOH, and the product eventually released from the resin with Mu ammonia solution in MeOH. The solution of crude product is concentrated under reduced pressure and purification of the residue gives the desired product. Starting from the compound of Preparation R and methyl 4-hydroxynicotinate and proceeding in analogy to Procedure AC, the title compound was obtained, after purification by prep-HPLC (acidic conditions) and treatment with HC1, as an amorphous solid (21% yield).MS (ESI, m/z): 381.28 [M+H+].

The synthetic route of 67367-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, 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, 135450-23-6, blongs to pyridine-derivatives compound. Quality Control of 6-(Chloromethyl)-2-cyanopyridine

Reference Example 150-1 tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-2-(1-methylcyclopropyl)-2-oxoethyl]-5-methoxyphenyl}carbamate Under an argon atmosphere, to a solution of tert-butyl {5-methoxy-2-[2-(1-methylcyclopropyl)-2-oxoethyl]phenyl}carbamate (300 mg) in N,N-dimethylformamide (3.1 mL) was added sodium hydride (50-72% in oil, 50 mg) under ice-cooling, and the mixture was stirred for 1 hour. 6-(Chloromethyl)pyridine-2-carbonitrile (158 mg) was added thereto in one portion, and the mixture was gradually warmed to room temperature. 13 Hours later, to the reaction mixture were added a saturated aqueous ammonium chloride solution and water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, 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 (271 mg). 1H-NMR (CDCl3) delta ppm: 0.62-0.73 (2H, m), 1.22-1.30 (5H, m), 1.57 (9H, s), 3.21 (1H, dd, J=8.2, 15.7 Hz), 3.54 (1H, dd, J=6.7, 15.7 Hz), 3.78 (3H, s), 4.68-4.78 (1H, m), 6.54-6.61 (1H, m), 6.95 (1H, d, J=8.5 Hz), 7.18-7.25 (1H, m), 7.33-7.40 (1H, m), 7.48-7.55 (1H, m), 7.64 (1H, t, J=7.8 Hz), 7.82 (1H, br s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 195044-14-5, Adding some certain compound to certain chemical reactions, such as: 195044-14-5, name is 2-Bromo-6-tert-butylpyridine,molecular formula is C9H12BrN, 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 195044-14-5.

Step-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 0.359 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (92.33 mg, 0.431 mmol, 1.2 eq) in 1,4 dioxane (5 mL) was added potassium carbonate (99.2 mg, 0.718 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (13.67 mg, 0.0718 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (12.65 mg, 0.143 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 16 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product which was purified by flash chromatography (Teledyne Isco Rf+); to afford 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(1,1,1-trifluoropropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3 (2H)-one (100 mg, 68.02%) as off white solid.

According to the analysis of related databases, 195044-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 823-61-0, 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. 823-61-0, name is 3,6-Dimethyl-2-pyridinamine. A new synthetic method of this compound is introduced below.

2) The obtained solution of O-(mesitylsulfonyl)hydroxylamine was added dropwise to a solution of commercially available 3,6-dimethyl-2-pyridinamine (16.4 g, 117 mmol) in DCM (100 mL) cooled in an ice bath. The mixture was then warmed to room temperature over 15 minutes. LCMS indicated almost complete conversion to the aminated intermediate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823-61-0, 3,6-Dimethyl-2-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; Kehler, Jan; Bang-Andersen, Benny; US2013/303770; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18368-73-5 , The common heterocyclic compound, 18368-73-5, name is 3-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, 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: To a stirred mixture of 1.00 mmol of nitropicoline 35 or 63, 1.20 mmol of the appropriate benzaldehyde, and 1.5 mmol of Huenig’s base in THF (7 mL/g of nitropicoline 35/63) was added 1.3 mmol of a 1 M THF solution of TBAF. The resulting mixture was heated 60 C for 1.5e2.0 h in the case of 2,3-dihydrofuro[3,2-c] pyridines or for 18 h in the case of 2,3-dihydrofuro[2,3-b]pyridines. After cooling to room temperature, the reactions were quenched with sat. aqueous NH4Cl. The solution was extracted with EtOAc, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography as specified above.

The synthetic route of 18368-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 920966-03-6, 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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Preparation 59To a suspension of 4-chloro-lH-pyrrolo [2, 3-b]pyridine-5-Carboxylic acid (343 mg) in N,N-dimethylformamide (4 ml) was added phenylmethanol (375 mul) 4-dimethylaminopyridine (428 nig) and N- [3- (dimethylamino) propyl] -N’ -ethylcarbodiimide hydrochloride (676 mg) . After stirring at ambient temperature for 3 days, the reaction mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform to give benzyl 4-chloro-lH-pyrrolo[2,3-b]pyridine-5-carboxylate (200 mg) as a yellow powder. 1H-NMR(DMSO-d6)OrS.40(2H,s) , 6.6 (IH, d, J=I.8Hz) , 7.35-7.39 (3H,m) , 7.41-7.45 (2H,m) ,7.71 (IH, d, J=3.5Hz) , 8.75 (IH, s) , 12.42 (IH, br) . EPO MS(ESI) :m/z 297.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,920966-03-6, 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

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

Adding a certain compound to certain chemical reactions, such as: 6945-67-1, 2-Bromo-4-nitropyridine, 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, Recommanded Product: 6945-67-1, blongs to pyridine-derivatives compound. Recommanded Product: 6945-67-1

The crude title compound from Step A above was dissolved in a mixture of degassed 1 ,4- dioxane (8.6 mL) and water (2 mL) in a microwave vial. Then [1 , 1 – bis(diphenylphosphino)ferrocene]dichloro-palladium(ll), complex with dichloromethane (0.034 g, 0.04 mmol), 2-bromo-4-nitropyridine (0.1 g, 0.49 mmol) and cesium carbonate (0.266 g, 0.82 mmol) were added and the reaction mixture was heated at ~1 15C in a sand- bath for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (30 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 00/0) to afford a mixture of the title compound and byproducts (0.076 g).

The synthetic route of 6945-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AC IMMUNE S.A.; PIRAMAL IMAGING SA; KROTH, Heiko; MOLETTE, Jerome; SCHIEFERSTEIN, Hanno; MUeLLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; ODEN, Felix; (72 pag.)WO2018/15546; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 84487-15-0, 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. 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine. A new synthetic method of this compound is introduced below.

4-Amino-5-nitropicolinonitrile (Compound 64) A solution of 2-bromo-5-nitropyridin-4-amine (135 mg, 0.619 mmol) and copper cyanide (67 mg, 0.743 mmol) in DMA was heated to 200 C. for 1 h using a microwave reactor. The reaction mixture was partitioned between water and EtOAc and tilted over celite. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by combiflash SiO2 chromatography using (0-50% EtOAc-hexanes) to give 4-amino-5-nitropicolinonitrile (70 mg, 69%) as a pale brown solid. 1H-NMR (400 MHz, CD3OD) delta ppm 9.07 (s, 1H), 7.37 (s, 1H); ESI-MS: m/z 164.77 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,84487-15-0, 2-Bromo-5-nitropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Stingray Therapeutics, Inc.; The University of Utah; Vankayalapati, Hariprasad; Liu, Xiaohui; Ramamoorthy, Gurusankar; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (59 pag.)US2019/31655; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3678-62-4, 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 3678-62-4, name is 2-Chloro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

(b); Into a 2L four-necked flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel, 356 g of methanol was charged, and 237.6 g (4.4 mol) of sodium methoxide was charged with stirring while keeping the temperature at 50C or below. Then, while keeping the temperature in the system at from 60 to 70C, 375.3 g of crude 2-chloro-4-methylpyridine (70.7%, 2.2 mol) obtained in the above Step was dropwise added over a period of 3 hours. After completion of the dropwise addition, reflux with heating was carried out for 3 hours while distilling methanol off (the amount of methanol distilled off over 3 hours was 120 g). After completion of the reaction, methanol remaining in the system was distilled off under reduced pressure, and 750 g of water was charged, so that the inorganic salt was dissolved. The formed oil was extracted with 1,050 g of diethyl ether, the aqueous layer was separated out, and the solvent was distilled off under reduced pressure to obtain 370 g of an oil (crude product). The purity of the obtained 2-methoxy-4-methylpyridine was 95% (two step yield from 2-amino-4-methylpyridine: 95%).

According to the analysis of related databases, 3678-62-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem