Month: April 2022

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

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

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

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 22282-70-8, 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.22282-70-8, name is 2-Fluoro-4-iodopyridine, molecular formula is C5H3FIN, molecular weight is 222.99, as common compound, the synthetic route is as follows.

Example 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H).

The chemical industry reduces the impact on the environment during synthesis 22282-70-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 718608-10-7 , The common heterocyclic compound, 718608-10-7, name is 5-(Bromomethyl)-2-methylpyridine hydrobromide, molecular formula is C7H9Br2N, 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 8-chloro-3-((1S,2S)-2-hydroxycyclohexyl)-6-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)quinazolin-4(3H)-one (130 mg, 0.321 mmol), cesium carbonate (314 mg, 0.964 mmol) and 5-(bromomethyl)-2-methylpyridine hydrobromide (103 mg, 0.385 mmol) in THF (5.0 ml) was sparged under nitrogen for 5 minutes. The mixture was treated with [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (26.2 mg, 0.032 mmol), sparged under nitrogen (3 minutes) and then heated at 60 C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (25 mL) and water (25 mL), and extracted with ethyl acetate (3 x 25 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (90:10 to 0:100; water containing 0.1% formic acid : acetonitrile containing 0.1% formic acid) to yield the title compound. 1H NMR (400MHz, CD3OD): delta 8.35 (d, J = 2.0 Hz, 2H), 8.02 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 7.62 (d, J = 8.0, 2.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 4.51- 4.49 (m, 1H), 4.13 (s, 2H), 4.07- 4.02 (m, 1H), 2.51 (s, 3H), 2.20- 2.10 (m, 1H), 1.97- 1.84 (m, 4H), 1.48- 1.46 (m, 3H) ppm. LRMS C21H23ClN3O2: calc?d 384.1, obs 384.2 (M+H) +.

The synthetic route of 718608-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56057-19-3 , The common heterocyclic compound, 56057-19-3, name is 6-Chloro-5-nitro-2-picoline, molecular formula is C6H5ClN2O2, 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.

C. 2-Phenyl-5-nitro-6-methylpyridine A mixture of Compound B and 2-chloro-3-nitro-6-methylpyridine (0.42 g, 2.40 mmol) in THF (10 mL) was degassed with nitrogen. Tetrakistriphenylphosphine palladium (28 mg, 0.024 mmol) was added and the mixture was stirred 30 minutes. 25 Phenylboronic acid (0.44 g, 3.6 mmol) and 2M Na2 CO3 (1.8 mL) were added and the mixture was heated at 75 C. for 17 hours and stirred at room temperature for 48 hours. Methylene chloride was added and the mixture was filtered through celite and partitioned. The mixture was washed with saturated aqueous NaHCO3, dried (magnesium sulfate), filtered and evaporated to afford 0.77 g of brown solid. Flash chromatography (silica, 10% ethyl acetate/hexanes) afforded 0.37 g of Compound C (72%) as an off white solid and 0.05 g of 2-phenyl-3-nitro-6-methylpyridine (10%) as an oil.

The synthetic route of 56057-19-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US6011029; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 81803-60-3, 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.81803-60-3, name is Ethyl imidazo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H10N2O2, molecular weight is 190.2, as common compound, the synthetic route is as follows.

To a solution of ethyl imidazo[1,5-a]pyridine-3-carboxylate (152 mg) in Acetic Acid (0.25M) was added Bromine (leq). The reaction was stirred at room temperature for 5 minutes thenconcentrated to dryness to give 205 of the title compound. This intermediate was taken onto the next step without purification.

The chemical industry reduces the impact on the environment during synthesis 81803-60-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 86847-84-9 ,Some common heterocyclic compound, 86847-84-9, molecular formula is C10H13ClN2O, 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 solution of iert-BuLi (1.7 M in pentane) was slowly added over half hour to a solution of compound 13-2 (1.25 g, 5.91 mmol) in anhydrous THF at -78 C. After the reaction was stirred for 3 h at -78 C, a solution of iodine (1.8 g, 7.09 mmol, 1.2 equiv.) in THF was added and the reaction mixture was allowed to warm up to room temperature and stirred for 14 h. The reaction was concentrated and the residue diluted with methylene chloride. The organic layer was washed sequentially with 10% aqueousNa2S203 and NaHC03 and concentrated under reduced pressure. The product was purified by flash chromatography using Combiflash and employing a gradient of 0-20% EtOAc in Hexanes to afford 1.50 g (4.45 mmol, 73% yield) of 13-3.

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. 86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 49669-13-8, Adding some certain compound to certain chemical reactions, such as: 49669-13-8, name is 2-Acetyl-6-bromopyridine,molecular formula is C7H6BrNO, 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 49669-13-8.

A solution of l-(6-bromopyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 mL) at 0C was treated with methyl magnesium bromide (8.33 mL, 25.0 mmol). After 3 hours, water was added to quench the excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound.Calc’d for C8HnBrNO [M+H]+: 216, Found: 216.

According to the analysis of related databases, 49669-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/156726; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem