Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, 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, Product Details of 153747-97-8, blongs to pyridine-derivatives compound. Product Details of 153747-97-8

To a solution of 4-(5-bromo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (250 mg, 0.73 mmol) in 3.5 mL anhydrous THF was added 1.6 M /j-butyllithium (500 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 min, the reaction mixture was charged with oxetan-3-one (131 mg, 1.82 mmol) in 200 muL DCM. The reaction mixture was stirred at -78 0C for 2 h and at room temperature for 16 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 – 100% EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford a off white solid (80 mg, 32.7% yield). The Boc protected title compound (140 mg, 0.417 mmol) was dissolved in DCM and charged with lutidine (194 muL, 1.67 mmol). The reaction mixture was cooled at 0 0C, charged with trimethylsilyl trifluoromethanesulfonate (1.25 mmol, 228 uL) and stirred at 0 0C for 2 h. The reaction mixture was poured into ice and the mixture was partitioned between DCM and water. The organic layer was dried over Na2SO4 and concentrated to afford a brown greasy solid (70 mg, yield 71%). MS (m/z, MH+): meas. 236.4 calc. 236.3

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26493-11-8 ,Some common heterocyclic compound, 26493-11-8, molecular formula is C6H7N3OS, 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 mixture of intermediate 3 (8 g, 39.8 mmol), copper (II) bromide (10.43 g, 46.68 mmol) and 3-methyl-l-nitrosooxy-butane (6.8 g, 58.35 mmol) in ACN (100 mL) was stirred at room temperature for 1.5 hours. The solvent was evaporated in vacuo. The residue thus obtained was dissolved in AcOEt and washed with H20. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo to yield 5 g (55%) of intermediate 4 that was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26493-11-8, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MACDONALD, Gregor, James; TRABANCO-SUAREZ, Andres, Avelino; CONDE-CEIDE, Susana; TRESADERN, Gary, John; BARTOLOME-NEBREDA, Jose, Manuel; PASTOR-FERNANDEZ, Joaquin; WO2011/73339; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 117873-72-0 , The common heterocyclic compound, 117873-72-0, name is 2,6-Dibromo-4-methoxypyridine, molecular formula is C6H5Br2NO, 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.

(1) Production of 2-bromo-4-methoxy-6-[3-(trifluoromethyl)phenoxy] pyridine as an intermediate 3-(trifluoromethyl) phenol (3.34 g; 0.0187*1.1 mol) was dissolved in dimethyl formamide (hereinafter referred to merely as “DMF”) (approximately 30 ml). Further, sodium hydride [0.78 g (ca. 60% in mineral oil), 0.0187*1.0 mol] and then 2,6-dibromo-4-methoxy pyridine (5.00 g, 0.0187 mol) were added to the solution. The obtained solution was stirred at about 120 C. for about 2 hours and, thereafter, allowed to stand so as to be cooled to room temperature. The obtained reaction solution was distributed in hexane-saturated sodium bicarbonate water. The organic phase separated from the reaction solution was washed with saturated brine, and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane), and the obtained purified product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield weight: 3.23 g; yield by percentage: 50%; solid; melting point: 57 to 60 C.; 1H-NMR (60 MHz, CDCl3, delta): 3.75(3H, s), 6.26(1H, d, J=2 Hz), 6.75(1H, d, J=2 Hz), 7.0-7.6(4H, complex).

The synthetic route of 117873-72-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Kagaku Kabushiki Kaisha; US6200933; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 696-42-4, 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. 696-42-4, name is 5-Fluoronicotinonitrile. A new synthetic method of this compound is introduced below.

A mixture of 5-fluoropyridine-3-carbonitrile (1 g, 6.55 mmol, 1 eq) and 4-methyl-lH-pyrazol-5- amine (707.02 mg, 6.55 mmol, 1 eq) in xylene (10 mL) was stirred at 70 C for 0.5 h. Then AlMe3 (2 M, 3.93 mL, 1.2 eq) was added to the mixture in one portion at 100 C. The mixture was stirred at 100 C for 16 h. The mixture was quenched with MeOH (30 mL) and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography (from DCM/MeOH = 1/0 to 5/1, TLC: DCM/MeOH = 5/1, Rf = 0.40) to yield product of 5-fluoro-N’-methyl-1H-pyrazol-5-yl)pyridine-3-carboxamidine (1.09 g, 3.86 mmol, 58.9% yield, 77.7% purity) as yellow oil. NMR (400 MHz, CD3OD) delta ppm 8.98 (s, 1H), 8.60 (d, J = 2.4 Hz, 1H), 7.38 (s, 1H), 7.17 (s, 1H), 2.14 (s, 3H); ES-LCMS m/z 220.2 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-42-4, 5-Fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
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 1227605-52-8, name is 2-Bromo-5-chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of 2,3-dibromo-5-chloropyridine (60 g, 221 mmol) in THF (500 mL) was added a solution of isopropylmagnesium chloride lithium chloride solution in THF (1.3M, 185 mL) at -40 C over about 30 min. The solution was stirred for 30 min at -40 C and DMF (50 mL) was added. The resulting solution was warmed up to room temperature and stirred for 30 min. The reaction was quenched with 1 N HCl (400 mL) and MTBE (200 mL) was added. Organic layer was separated and washed twice with 5% aqueous NaHC03 (200 mL). The solvent was removed under vacuum at 50 C. The resulting solids (aldehyde intermediate) were dissolved in methanol (400 mL). The solution was cooled to 5 C under an ice bath. NaBtit (3.6 g) was added slowly over 30 min while maintaining the reaction temperature below room temperature. The reaction mixture was stirred for another 30 min followed by addition of water (125 mL). The resulting mixture was concentrated under vacuum to approximately 150 ml. Solids precipitated during the concentration. The suspension was stirred vigorously at room temperature for 1 h and solids were collected by filtration. The wet cake was dried in a vacuum oven over night at 60 C to give 1 (45.6 g, 93%) as a solid. 1H NMR (CDC13) 400 MHz): <5 8.26 (d, J= 2.5 Hz, 1H), 7.88 (d, J=2.5 Hz, IK), 4.73 (d, J= 5.8 Hz, 2H), 2.33 (t, J= 1 1.4 Hz, 1H); 13C NMR (CDC13, 100 MHz): delta 147.12, 138.48, 138.39, 136.14, 132.06, 62.76. With the rapid development of chemical substances, we look forward to future research findings about 1227605-52-8. Reference:
Patent; MERCK SHARP & DOHME CORP.; XIANG, Bangping; YASUDA, Nobuyoshi; WO2013/138413; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1227384-81-7, 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. 1227384-81-7, name is 2-Bromo-5-(ethylsulfonyl)pyridine, molecular formula is C7H8BrNO2S, 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.

Under nitrogen atmosphere,750 mg of 2-bromo-5- (ethanesulfonyl) pyridine,811 mg of 3- (trifluoromethanesulfonyl) aniline,Potassium t-butoxide 504 mg,And a mixture of 10 mL of 1,4-dioxaneTris (dibenzylideneacetone) dipalladium (0)60 mg and54 mg of 1,3-bis (2,6-diisopropylphenyl) imidazolium chloride are sequentially added,Stir at 100 C.After completion of the reaction, the resulting mixture is brought to room temperature,Add water and extract with ethyl acetate.The resulting organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure.The resulting residue is subjected to silica gel column chromatography.2-{[3- (Trifluoromethanesulfonyl) phenyl] amino} -5- (ethanesulfonyl) pyridine is obtained.

According to the analysis of related databases, 1227384-81-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Chemicals company; Sasayama, Daisuke; Inui, Tomohiko; (102 pag.)JP2019/48845; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1256785-86-0 ,Some common heterocyclic compound, 1256785-86-0, molecular formula is C7H8N2O, 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 1-(4-aminopyridin-2-yl)ethan-1-one (29.3, 5 g, 36.72 mmol) in ACN/THF (1:1 (v/v), 50 mL) and pyridine (4.74 g, 59.92 mmol) at 0 C. was added dropwise phenyl chloroformate (4.68 g, 29.89 mmol). The resulting solution was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum and washed with ether (2*30 mL) to provide the desired product as a yellow solid (9 g, crude), which was used as is without further purification. LC-MS (ES, m/z): 257 [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,1256785-86-0, its application will become more common.

Reference:
Patent; MyoKardia, Inc.; Oslob, Johan; Aubele, Danielle; Kim, Jae; McDowell, Robert; Song, Yonghong; Sran, Arvinder; Zhong, Min; (120 pag.)US2016/243100; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 185315-51-9, 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. 185315-51-9, name is 2-(5-Chloropyridin-2-yl)acetonitrile, molecular formula is C7H5ClN2, 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.

General procedure: To a solution of ethylo-mesitylsulfonylacetohydroxamic acid (2.14 g, 7.50 mmol) in 1,4-dioxane (4 mL)was added a 70% aqueous solution ofhydrogenperchlorate (0.8 mL, 9.2 mmol), and the mixture was stirred at 0C for 0.5 h. After the addition of ice-water, theprecipitate was collected. The cake was dissolved in dichloromethane (20 mL)and dried over Na2SO4. To themixture was added a solution of 2-pyridineaceonitrile substrate(5.00 mmol) in dichloromethane (5 mL), and then the mixture was stirred at roomtemperature for 1 h. The mixture was concentratedin vacuo to give 1-aminopyridinium2,4,6-trimethylbenzenesulfonate intermediate as a crude material. To a solutionof the crude material in methanol (25 mL) was added potassium carbonate (1.38g, 9.98 mmol) at 0C,and then the mixture was stirred at room temperature for 2 h. After the addition of water, the mixture wasextracted with ethyl acetate, then washed with water and brine, and then driedover Na2SO4. Themixture was concentrated in vacuo. Thecrude material waspurified by flash column chromatography on a silica gel(Hexane:AcOEt) togive 1a-g.

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 185315-51-9, 2-(5-Chloropyridin-2-yl)acetonitrile.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Yamamoto, Eri; Kohno, Yasushi; Seto, Shigeki; Tetrahedron Letters; vol. 55; 43; (2014); p. 5963 – 5966;,
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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid, molecular formula is C6H3FINO2, 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. Application In Synthesis of 2-Fluoro-4-iodonicotinic acid

To a solution of 401-C (10.3 g, 38.6 mmol) in 40 mL of MeOH and Et2O (40 mL) cooled with ice-water, TMSCH2N2(29 mL, 57.9 mmol) was added dropwise. The mixture was stirred at 25 C for overnight. Then ice water was added toquench the reaction. The solvent was removed by evaporation and Sat. NaHCO3 was added and the mixture was stirredfor 30 minutes. The mixture was extracted with EtOAc (100 mL3). The combined organic phase was washed with brine,dried over Na2SO4, filtered and concentrated to dry to give product 401-D (methyl 2-fluoro-4-iodonicotinate, 9.6 g, yield:88%).1H NMR (300 MHz, DMSO-d6): delta 8.06 (d, J = 5.4 Hz, 1H), 7.97 (d, J = 5.1 Hz, 1H), 3.93 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 884494-51-3.

Reference:
Patent; Kangpu Biopharmaceuticals, Ltd.; LEE, Wen-Cherng; LIAO, Baisong; ZHANG, Lei; EP3590924; (2020); 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. 22282-70-8, name is 2-Fluoro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Fluoro-4-iodopyridine

A solution of 401-A (21.6 g, 96.9 mmol) in 100 mL of dry THF was cooled to -70 C. The above LDA solutionwas added dropwise to the solution while the temperature was kept below -70 C. Then the solution was stirred at -70C for 1 hour. Ethyl formate (10 mL, 121 mmol) was added dropwise to the solution and slowly warmed to -50 C during1 hour. The reaction mixture was quenched with sat. NH4Cl and stirred at 25 C for 30 minute. THF was removed byevaporation and the reaction solution was extracted with EtOAc (300 mL2). The combined organic phase was washedwith water and brine, dried over Na2SO4. Na2SO4 was filtered and the organic phase was concentrated to dry and theresidue was purified by column chromatography on silica gel (PE/EtOAc: 50:1 to 10:1) to give the product 401-B (2-fluoro-4-iodonicotinaldehyde, 13.0 g, yield: 53%).1H NMR (300 MHz, DMSO-d6): delta 10.15 (s, 1H), 7.97 (d, J = 5.1 Hz, 1H), 7.87 (d, J = 5.1 Hz, 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, 22282-70-8, 2-Fluoro-4-iodopyridine.

Reference:
Patent; Kangpu Biopharmaceuticals, Ltd.; LEE, Wen-Cherng; LIAO, Baisong; ZHANG, Lei; EP3590924; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem