Day: April 15, 2022

Synthetic Route of 116026-95-0, 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. 116026-95-0, name is tert-Butyl (4-formylpyridin-3-yl)carbamate, molecular formula is C11H14N2O3, 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.

(4-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (100 mg) was dissolved in a hydrochloric acid-methanol solution (2.0 ml), and the solution was stirred under reflux for 30 min. The solvent was removed by distillation under the reduced pressure. 1-Chloro-propan-2-one (42 mg) dissolved in a 5 N aqueous sodium hydroxide solution (0.5 ml) was added to the residue, and the mixture was allowed to stand in an airtightly stoppered state for two days. The reaction mixture was neutralized with 10% hydrochloric acid, and dichloromethane was then added thereto for extraction. The dichloromethane layer was washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a chloroform-acetone system to give 2-methyl-[1,7]naphthyridin-3-ol (22 mg, yield 31%). 2-Methyl-[1,7]naphthyridin-3-ol (22 mg), 4-chloro-6,7-dimethoxyquinoline (92 mg), and 4-dimethylaminopyridine (50 mg) were suspended in 1,2-dichlorobenzene (1.5 ml), and the suspension was stirred at 140C for 8.5 hr. The reaction mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with chloroform, and the chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a chloroform-methanol system to give the title compound (25 mg, yield 53%). 1H-NMR (CDCl3, 400 MHz): delta 2.76 (s, 3H), 4.01 (s, 3H), 4.06 (s, 3H), 6.54 (d, J = 5.6 Hz, 1H), 7.44 (s, 1H), 7.49 (s, 1H), 7.52 (d, J = 6.0 Hz, 1H), 7.61 (s, 1H), 8.57 (m, 2H), 9.45 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 348 (M+1)+ (4-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (100 mg) was dissolved in a hydrochloric acid-methanol solution (2.0 ml), and the solution was stirred under reflux for 30 min. The solvent was removed by distillation under the reduced pressure. 2-Chloro-1-phenyl-ethanone (70 mg) dissolved in a 5 N aqueous sodium hydroxide solution (0.6 ml) was then added to the residue, and the mixture was allowed to stand in an airtightly stoppered state for two days. The reaction solution was neutralized with 10% hydrochloric acid, and dichloromethane was then added thereto for extraction. The dichloromethane layer was washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a chloroform-acetone system to give 2-phenyl-[1,7]naphthyridin-3-ol (3 mg, yield 3%). 2-Phenyl-[1,7]naphthyridin-3-ol (3 mg), 4-chloro-6,7-dimethoxyquinoline (9 mg), and 4-dimethylaminopyridine (5 mg) were suspended in 1,2-dichlorobenzene (1.0 ml), and the suspension was stirred at 140C for 9 hr. The reaction mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with chloroform, and the chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a chloroform-methanol system to give the title compound (3 mg, yield 54%). 1H-NMR (CDCl3, 400 MHz): delta 4.00 (s, 3H), 4.07 (s, 3H), 6.59 (d, J = 5.6 Hz, 1H), 7.39 (m, 4H), 7.61 (m, 2H), 7.86 (s, 1H), 7.98 (m, 2H), 8.50 (d, J = 5.6 Hz, 1H), 8.64 (d, J = 5.6 Hz, 1H) 9.62 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 432 (M+Na)+

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 116026-95-0, tert-Butyl (4-formylpyridin-3-yl)carbamate.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, the common compound, a new synthetic route is introduced below. Product Details of 61494-55-1

To 30 ml of a THF solution containing 700 mg of 2-(2-chloropyridin-3-yl)acetic acid was added dropwise 7.75 ml of a 1.9 mol/L THF solution of hexamethyldisilazane sodium at -78 C. and the mixture was stirred for 10 minutes. Then, 616 mul of methyl 2,6-difluorobenzoate was added dropwise thereto, and then, the temperature of the mixture was raised from -78 C. to room temperature and stirred for 1 hour. To the mixture was added an aqueous saturated ammonium chloride solution followed by stirring the mixture for 1 hour. Thereafter, ethyl acetate was added thereto and the liquids were separated. The obtained organic layer was washed with saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 450 mg of a transparent oily product. (1215) 1H-NMR (CDCl3) delta: 8.35 (1H, dd, J=4.7, 1.8 Hz), 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.44-7.43 (1H, m), 7.25 (2H, dd, J=7.6, 4.7 Hz), 7.00-6.96 (2H, m).

The synthetic route of 61494-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUI CHEMICALS AGRO, INC.; UMETANI, Hideki; OKAYA, Shun; IKISHIMA, Hideaki; FUKUMOTO, Takeshi; NISHIDA, Akihiro; YANAGI, Masanori; NAITO, Ryohei; MASUTOMI, Koji; SHIRAKAWA, Tomomi; SAKURADA, Akane; YUTANI, Satoshi; (368 pag.)US2020/45968; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 189230-41-9, 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 189230-41-9, name is 2-Bromopyridine-3,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To a solution of 2-fluoro-6-iodobenzaldehyde (1.5 g, 6.0 mmol) and 2-bromopyridine-3,4-diamine (1.1 g, 6.0 mmol) in ethanol (20 mL), was added ferric chloride (778 mg, 4.80 mmol). The reaction mixture was stirred at 60 C. under oxygen atmosphere overnight. The next day, solvent was evaporated via rotavap and theresulting residue was purified by column chromatography on silica gel eluting with petroleum/ethyl acetate (3:1) to give the desired product (1.6 g, 64% yield) as a yellow solid. LCMS (ESI) m/z: 418 [M+H+].

According to the analysis of related databases, 189230-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Lai, Yingjie; Liang, Jun; Magnuson, Steven R.; Robarge, Kirk D.; Tsui, Vickie H.; Zhang, Birong; US2014/206702; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55304-80-8, 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 55304-80-8, name is 2,6-Dibromo-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

2,6-Dibromo-3-nitropyridine (700.0 mg, 2.48 mmol) was added to 2M ammonia solution in EtOH (25.0 mL, 49.66 mmol). The mixture stirred at room temperature for 12 hours and concentrated under reduced pressure to obtain yellow solid compound of 6-bromo-3-nitropyridin-2-amine (526.0 mg, 97%). [1220] 1H-NMR (400 MHz, DMSO-d6); delta: 8.26 (m, 3H), 6.91 (d, 1H, J=8.4 Hz)

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 55304-80-8, 2,6-Dibromo-3-nitropyridine.

Reference:
Patent; C&C RESEARCH LABORATORIES; Ho, Pil Su; Yoon, Dong Oh; Han, Sun Young; Lee, Won Il; Kim, Jung Sook; Park, Woul Seong; Ahn, Sung Oh; Kim, Hye Jung; US2014/315888; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 3430-26-0, name is 2,5-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 3430-26-0

5-bromo-4-methyl-pyridine-2-carbonitrile: To a solution of 2,5-dibromo-4-methylpyridine (15 g, 59.8 mmol, Eq: 1.00) in DMF (100 ml) was added copper(I) cyanide (4.28 g, 47.8 mmol, Eq: 0.8) and sodium cyanide (2.34 g, 47.8 mmol, Eq: 0.8). The reaction mixture was refluxed for 20 hr at which point a precipitate formed. Upon cooling water was added and the mixture sonicated. The solids were filtered and washed with water. The resulting filtrate was extracted with EtOAc and the organic layers then combined, washed with water and brine, and concentrated under reduced pressure. The crude material was then purified by column chromatography (0-10% EtOAc/Hex gradient) to give 5-bromo-4-methyl-pyridine-2-carbonitrile (5 g, 42.4% yield) as a white 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, 3430-26-0, 2,5-Dibromo-4-methylpyridine.

Reference:
Patent; Hoffmann-La Roche Inc.; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90333; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 61494-55-1, 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 61494-55-1 as follows.

Acetyl chloride (0.651 mL, 9.16 mmol) was added to a suspension of (2- chloropyridin-3-yl)acetic acid (1117) (1.048 g, 6.108 mmol) in MeOH (30 mL). The mixture was heated at reflux for 20 hours. The volatiles were removed in vacuo and the residue partitioned between OCM (100 mL) and sat. NaHC03 ( 100 mL). The layers were separated and the aqueous layer extracted with DCM (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2S0 ) and the solvent removed under reduced pressure to yield an oil which was purified by column chromatography on silica gel (0-40% EtOAc in petroleum benzine 40-60 C) to afford the title compound (1118) (0.863 g, 76%) as a pale yellow oil; NMR (400 MHz, dr D SO) delta 8.34 (dd, J = 4.8, 1.9 Hz, H), 7.88 (dd, J – 7.5, 1.9 Hz, 1 H), 7.43 (dd, J.= 7.5, 4.8 Hz, 1 H), 3.86 (s, 2H), 3.65 (s, 3H). LCMS Method C: rt 5.04 min; m/z 186 [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,61494-55-1, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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