Category: pyridine-derivatives

Synthetic Route of 274-76-0 ,Some common heterocyclic compound, 274-76-0, molecular formula is C7H6N2, 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 DMF (120 mL, 1.55 mol) at 2 C, freshly distilled phosphorus oxychloride (61 mL, 0.65 mol) was slowly added. The temperature was allowed to rise gradually to room temperature. The solution was cooled again to 2 C and a solution of imidazo[1,2-a]-pyridine 1 (10 g, 0.085 mol) in DMF (60 mL) was added dropwise. The mixture was warmed to 105 C, whereupon the temperature rose to 140 C. The oil bath was removed until the temperature stabilized at 120 C. The reaction mixture was heated for 45 min at 120 C and 2.5 h at 85 C, then cooled and poured into 5% HCl (600 mL) ice-cooled and brought to pH 9 using 20% NaOH. The resulting solution was extracted with CH2Cl2 (1200 mL) overnight. Then the organic layer was separated and dried over MgSO4, the solvent removed under reduced pressure, the crude product washed with water (5 × 15 mL) and again dried, providing the pure product 3.49 g (31%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,274-76-0, its application will become more common.

Reference:
Article; B?aewska, Katarzyna M.; Ni, Feng; Haiges, Ralf; Kashemirov, Boris A.; Coxon, Fraser P.; Stewart, Charlotte A.; Baron, Rudi; Rogers, Michael J.; Seabra, Miguel C.; Ebetino, Frank H.; McKenna, Charles E.; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4820 – 4826;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 91678-23-8, Adding some certain compound to certain chemical reactions, such as: 91678-23-8, name is 2-Bromo-6-chloro-3-nitropyridine,molecular formula is C5H2BrClN2O2, 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 91678-23-8.

Under nitrogen a solution of 2-bromo-6-chloro-3-nitropyridine (2.5 g, 10.53 mmol, 1.00 equiv) in THF (60 mL) was cooled to -78 C. and bromo(ethenyl)magnesium (1M in THF, 63 mL, 6 equiv) was added dropwise. The reaction was stirred for 1 h at -50 C., quenched with aqueous ammonium chloride, extracted with ethyl acetate, dried over sodium sulfate, and concentrated in vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3). This resulted in the title compound (1.3 g, 53%) as a yellow solid. LC-MS (ES, m/z): 231 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 91678-23-8, 2-Bromo-6-chloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); 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. 670253-37-9, name is 4-Chloro-5-iodopyridin-2-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Chloro-5-iodopyridin-2-amine

A mixture of 4-chloro-5-iodopyridin-2-amine (2.8 g, 1 1 mmol), Pd(PPh3)4 (1.9 g, 1.65 mmol), and Zn(CN)2 (0.7 g, 6.05 mmol) in NMP (30 mL) was heated at 130C for 5 hours. The reaction mixture was cooled to 23C, diluted by H20 (200 mL) and filtered. The solid was purified by silica gel chromatography using Petroleum Ether:EtOAc (3: 1 ) as eluting solvents to afford 2-(3H- imidazo[4,5-b]pyridin-3-yl)acetimidamide as a yellow solid (1.18 g, 70%). MS (ESI) m/z: 154 [M+H]+.

The synthetic route of 670253-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEAUFOUR IPSEN TIANJIN PHARMACEUTICAL CO., LTD; AUVIN, Serge; LAVERGNE, Olivier; CHAO, Qi; CHEN, Yufeng; WO2015/100609; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 685115-77-9, 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 685115-77-9 as follows.

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (0.10 g, 0.36 mmol) in polyphosphoric acid (5 ml.) at 80 0C was added vinylene carbonate (35 mg,0.40 mmol). The mixture was heated at 170 0C for 4 hours, cooled to r.t. and poured into water (200 ml_). The mixture was extracted with ethyl acetate (3 x 50 ml.) and the combined organic extracts were washed with water (100 ml_), a saturated solution of sodium hydrogen carbonate (50 ml_), water (50 ml_), brine (50 ml_), dried (MgSO4) and concentrated under reduced pressure to furnish a colourless oil (12 mg). The crude product was purified by preparative tic on silica gel (CH2CI2, MeOH, 10:1 then hexane,EtOAc, 1 :1 ) to furnish the title compound as a white solid (13 mg, 12%), LC-MS (ESI) Rt 2.66 min, m/z 298 (100%, M+); m/z (ESI) Ci3H14CI2N3O requires 298.0508 found [M+H]+ 298.0507.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,685115-77-9, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53636-70-7, 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 53636-70-7 as follows.

In a 100 ml round-bottomed flask 6-methyl-2,3-pyridinedicarboxylic acid (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D60 (8.2 g) as a slightly brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53636-70-7, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 858116-66-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.858116-66-2, name is 5-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C16H25BrN2Si, molecular weight is 353.3726, as common compound, the synthetic route is as follows.

To a 50 ml reaction flask at room temperature, the compound of formula II (4.08 g, 11.5 mmol) was added, Copper acetylacetonate (0.15g, 0.575mmol), BetaEtaMuRhoO (0.15g, 0 · 575mmol), lithium hydroxide monohydrate (2 · 42g, 57.5mmol), 18ml of DMSO, 4.5ml of water, stirring was turned on, replaced with nitrogen, and the temperature was raised to an internal temperature of 100 C. Temperature reaction for 6 hours. Control raw material reaction is over, stop heating, cool to room temperature (20-30 C), add water 100ml, adjust PH to 6 with 2N dilute hydrochloric acid, precipitation of solids, suction filtration, aqueous phase with ethyl acetate 50ml * 3 Extraction, combining the organic phases, washing once with water and saturated aqueous sodium chloride solution, drying over anhydrous sodium sulfate, and concentrating the solvent to obtain the compound of formula III. Yield: 1.2 g, yield: 78.5%.

The chemical industry reduces the impact on the environment during synthesis 858116-66-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Hongbozhiyuan Pharmaceutical Co., Ltd.; Zhuang Yinqiang; Peng Shaoping; Jiang Hui; (11 pag.)CN107434807; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83766-88-5, 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 83766-88-5 as follows.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 119248-43-0, 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 119248-43-0, name is 1H-Pyrrolo[3,2-c]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 83 (2-Methyl-3-phenyl-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)(1H-pyrrolo[3,2-c]pyridin-3-yl)methanone The title compound was prepared in a manner analogous to Example 1, using 1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid instead of 1-naphthoic acid, triethylamine instead of DIPEA, and ethyl acetate instead of DCM. MS (ESI): mass calcd. for C21H19N5O, 357.2; m/z found, 358.3 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 12.51-11.44 (m, 1H), 9.02-8.91 (m, 1H), 8.25-8.14 (m, 1H), 7.94-7.79 (m, 1H), 7.56-7.36 (m, 6H), 4.75 (s, 2H), 3.93-3.77 (m, 2H), 3.73 (s, 3H), 2.72-2.59 (m, 2H).

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 119248-43-0, 1H-Pyrrolo[3,2-c]pyridine-3-carboxylic acid.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (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. 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-(Chloromethyl)-2-cyanopyridine

Intermediate HU (1754) 6-((2-Bromophenoxy)methyl)picolinonitrile (1755) To a sealable 4 mL vial, containing 6-(chloromethyl)picolinonitrile (100 mg, 0.66 mmol) and 2-bromophenol (113 mg, 0.66 mmol), were added Cs2CO3 (320 mg, 0.98 mmol) and acetonitrile (1.7 mL). The vial was then heated at 80 Celsius for 15 hours. The reaction was then diluted with ethyl acetate, filtered through a celite plug and concentrated to dryness. The material was used without further purification. 1H NMR (500 MHz, CDCl3) delta 8.02-7.93 (m, 1H), 7.93-7.85 (m, 1H), 7.65-7.59 (dd, J=7.7, 1.1, 1H), 7.58-7.53 (dd, J=7.9, 1.6, 1H), 7.29-7.22 (m, 1H), 6.93-6.90 (dd, J=8.3, 1.3, 1H), 6.90-6.86 (m, 1H), 5.23 (s, 2H).

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, 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Bacani, Genesis M.; Eccles, Wendy; Fitzgerald, Anne E.; Goldberg, Steven D.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Lee-Dutra, Alice; Liu, Jing; McClure, Kelly J.; Meduna, Steven P.; Pippel, Daniel J.; Rosen, Mark D.; Sales, Zachary S.; US2015/259357; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-47-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.

Step 1 [0610] A suspension of 2-bromo-4-methyl-5-nitropyridine (XIV) (200 g, 921 mmol, 1.00 eq) and NH4C1 (240 g, 4.49 mol, 4.87 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 50C. To this mixture was added Fe ( 120 g, 2.15 mol, 2.33 eq) and HC1 (10.2 g, 279 mmol, 0.30 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 L x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-4-methylpyridin-3 -amine (XV) as brown solid (167.9 g, 898 mmol, 97.4% yield) which was used for the next step without any purification. l NMR (CDC , 400 MHz) delta ppm 2.15 (s, 3H), 3.44 (br s, 2H), 7.14 (s, 1H), 7.78 (s, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).

The chemical industry reduces the impact on the environment during synthesis 23056-47-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (261 pag.)WO2017/23984; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem