Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1214323-40-6, 5-Chloro-2-(difluoromethoxy)pyridine, 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 1214323-40-6, blongs to pyridine-derivatives compound. Product Details of 1214323-40-6

A stirred mixture of 5-chloro-2-(difluoromethoxy)pyridine (0.13 g, 0.75 mmol), bis(pinacolato)diboron (0.21 g, 0.83 mmol), [l,l-bis(diphenylphosphino)- ferrocene]palladium(II) chloride, complex with DCM (62 mg, 0.076 mmol), and potassium acetate (0.23 g, 2.3 mmol) in dry 1,4-dioxane (4 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 90 C and monitored with LC-MS and TLC. After 21 h, the reaction was cooled to rt then filtered through Celite. The organic solvent was removed under reduced pressure, and the black residue was identified as (6-(difluoro- methoxy)pyridin-3-yl)boronic acid, used without purification.

The synthetic route of 1214323-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); 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. 13362-30-6, name is Ethyl 2-aminoisonicotinate, the common compound, a new synthetic route is introduced below. Product Details of 13362-30-6

Example 97 Preparation of ethyl 2-valeramidoisonicotinate ([9]-(94)-467) The compound ([9]-(93)-467′) (2.0691 g) prepared in Example 96 was dissolved in anhydrous pyridine (25 ml), and valeryl chloride (1.5 ml) was added dropwise to the solution with stirring and cooling on ice. After stirring and cooling on ice for 1 hour, the reaction solution was poured into ice water. The solution was extracted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The resulting light yellow oil (3.2548 g) was purified by silica gel column chromatography (Kieselgel 60=160 g, hexane/ethyl acetate=5/1) to obtain the above-captioned compound ([9]-(94)-467) (3.0820 g) as white crystals. Melting point: 46.0-47.0 C. 1 H-NMR (500MHz, CDCl3) delta: 0.96 (t, 3H), 1.41 (t, 3H), 1.43 (sext, 2H), 1.74 (quint, 2H), 2.42 (t, 2H), 4.41 (q, 2H), 7.60 (dd, 1H), 8.04 (bs, 1H), 8.38 (dd, 1H), 8.74 (s, 1H)

The synthetic route of 13362-30-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; US5696118; (1997); A;,
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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine

To a solution of butyl magnesium chloride (27.8mL, 47.2mmol, 0.7eq, 1.7 M in THF) in THF was added butyl lithium (30.0mL, 74.3mmol, l. leq, 2.5M in hexane) at 0C and the reaction mixture was stirred for 10 min, then diluted with THF (80mL) and cooled to -78C. Then, 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (17.5g, 67.5mmol, leqm procedure described in Example 93) in THF (30mL) was added and the reaction mixture was stirred for lh at same temperature, before being poured onto crushed dry ice then slowly allowed to warm to RT for 16h. TLC indicated polar spot and the reaction mixture was concentrated and acidified with 2N HC1 (80mL) and extracted with EtOAc (2X 500mL). The organic layer was separated, dried with sodium sulfate and concentrated under reduced pressure to give crude residue. The crude compound was recrystallized from n-pentane (30mL) and dried using high vacuum to give 6-chloro-4-(trifluoromethyl)nicotinic acid (lOg, 66.6%) as an off white solid compound. LCMS: [M+H]+ 224.05.

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, 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 97986-08-8, 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. 97986-08-8, name is N,6-dimethylpyridin-2-amine. A new synthetic method of this compound is introduced below.

Example 110 4′-Cyano-biphenyl-4-sulfonic acid methyl-(6-methyl-pyridin-2-yl)-amide To a solution of N,6-dimethylpyridin-2-amine (0.15 g, 1.24 mmol) in THF (5 ml) was added NaHMDS (1.56 mL, 1.56 mmol) at R.T. After 15 min, 4′-cyanobiphenyl-4-sulfonyl chloride (0.28 g, 1.03 mmol) was added to the reaction mixture and stirred for 1 hour. The reaction mixture was diluted with ethyl acetate (30 mL) and washed with saturated aqueous sodium bicarbonate (2*30 mL). The collected organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified with radial chromatography (2 mm silica plate, 2:1 hexanes/ethyl acetate) to yield a clear oil. The product was converted to a HCl salt by dissolving in 5 mL diethyl ether and adding 1 N HCl in diethyl ether dropwise.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97986-08-8, its application will become more common.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; US2005/148631; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-40-8, Adding some certain compound to certain chemical reactions, such as: 23056-40-8, name is 2-Chloro-5-methyl-3-nitropyridine,molecular formula is C6H5ClN2O2, 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 23056-40-8.

Synthesis of the compound 16 The compound 15 (3 g, 0.017 mol) was dissolved with agitation in a concentrated sulphuric acid (80 mL) in ice bath , the sodium dichromate (7.5 g, 0.025 mol) was added slowly in batches into the system, and the reaction was run at room temperature (25C) for 12 h. The above reaction liquid was added slowly into broken ice (50 g) and extracted with 50mL of ethyl acetate for three times. The extracts were combined, washed with a saturated aqueous solution of table salt, dried over anhydrous magnesium sulfate, and then was subject to filtration. The solvent was evaporated off and 2.9 g of the crude product was obtained with a yield of 82.8%. The crude product was recrystallized in ethanol to obtain 2.4 g of the solid product with a yield of 68.6 % and a melting point of 218C (ethanol)[J.O.C., 1985, 50, 1041].

According to the analysis of related databases, 23056-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Yiling Bioengineering Co., Ltd.; EP2366691; (2011); A1;,
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

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

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

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

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