Category: pyridine-derivatives

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.911434-05-4, name is 5-Bromo-2-methyl-3-nitropyridine, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.Recommanded Product: 911434-05-4

j00130j 5-Bromo-2-methyl-3-nitropyridine (2.00 g, 9.22 mmol) was dissolved in THF (92 mL) and the solution was cooled to -50 C under an atmosphere of argon. Vinylmagnesium bromide (1 M in THF, 27.6 mL, 27.6 mmol) was added in one portion and the reaction mixture turned orange. The reaction was allowed to stir at -40 C for 30 mm and then quenched the reaction with saturated ammonium chloride solution. The mixture was extracted with EtOAc, the combined organic layers dried with MgSO4 and concentrated by rotary evaporation. The crude material was purified by column chromatography to yield 4-bromo-7-methyl-1H-pyrrolo[2,3-c]pyridine (0.711 g, 36.6%). LCMS (FA): m/z = 211.0, 213.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,911434-05-4, 5-Bromo-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; XU, He; YE, Yingchun; WO2015/108881; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 116834-96-9, 3-Methyl-1H-pyrazolo[3,4-b]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, 116834-96-9, blongs to pyridine-derivatives compound. Recommanded Product: 3-Methyl-1H-pyrazolo[3,4-b]pyridine

Step 4 To a solution of NaOH (0.88 g, 22 mmol) in water (20 mL) was added 3-methyl-1H-pyrazolo[3,4-b]pyridine (XII) (0.4 g, 3 mmol). The suspension was heated at 80 C. until a clear solution was obtained. A solution of KMnO4 (1.73 g, 11 mmol) in water (180 mL) was added slowly over 2 h while heating the solution at 80 C. The solution was heated at 90 C. for an additional 2 h until the complete disappearance of starting material was observed by TLC. The solution was cooled to 70 C. and filtered through a pad of Celite. The solids were washed by boiling water. The combined filtrate was cooled to 0 C., acidified with conc. H2SO4 to pH=2 and extracted with n-butanol (2*10 mL). The n-butanol layer was concentrated under reduced pressure to get a white residue which was dissolved in DCM by adding minimum amount of MeOH and then filtered. The filtrate was concentrated to give 1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XIII) as a white solid (390 mg, 2.39 mmol, 81% yield). 1H NMR (CDCl3) delta ppm 7.37 (dd, J=8.10 Hz, J=4.52 Hz, 1H), 8.47 (dd, J=7.54 Hz, J=1.88 Hz, 1H), 8.62 (dd, J=4.52 Hz, J=1.32 Hz, 1H), 14.37 (brs, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116834-96-9, its application will become more common.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 126325-53-9, Adding some certain compound to certain chemical reactions, such as: 126325-53-9, name is 2-Bromo-6-methylpyridin-3-amine,molecular formula is C6H7BrN2, 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 126325-53-9.

General procedure: 3-Amino-2-bromo-6-methylpyridine(7a) or4-amino-2-bromo-6-methylpyridine(7b) (25.20 g, 134.73 mmol) wasadded to a mixture of water (78.1 mL) and conc. HCl (12.8 mL, 350.30 mmol), andthen the mixture was cooled to 0 oC. To it, sodium nitrite (18.6 g,269.46 mmol) was added portionwise with stirring over a period of 20 min whilekeeping the reaction temperature between -5 oCand 0 oC. After 10 min, 65% hexafluorophosphoric acidsolution (43.26 g, 296.41 mmol) was added dropwise with cooling, atwhich point a lot of precipitates were formed. The precipitates were collectedby filteration using a glass filter funnel, washed with cold water (2 × 50 mL) and diethyl ether (100 mL), and then dried in the air for 48 h.The solid was slowly heated to 100 oC (very exothermic), and a darkred oily material was formed after 10 min. The oil was basified with dilutedNaOH solution to pH~10 and extracted with CH2Cl2 (2 × 150 mL). The combined organic layer was dried over anhydrous Na2SO4,filtered, and evaporated to dryness under reduced pressure. The residue waspurified by MPLC on neutral alumina using hexane/EtOAc (10:1) as eluent to affordthe titled compounds.

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. 126325-53-9, 2-Bromo-6-methylpyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Krishnaiah, Maddeboina; Jin, Cheng Hua; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5228 – 5231;,
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. 1195-59-1, name is 2,6-Pyridinedimethanol. A new synthetic method of this compound is introduced below., Recommanded Product: 1195-59-1

The 2,6-dimethylolpyridine (10.0g, 71. 9mmol) by adding 250 ml three flasks, constant voltage used in the dropping funnel slowly dropping 48% of HBr (95 ml) solution dissolved, after maintaining the 60 C magnetic stirring for 19 hours. After the end of the reaction cooled to the room temperature, and then to continue to use the ice ice salt bath cooling and saturation of the sodium accent carbonate to alkaline. The generated white solid after filtering, washing several times with distilled water, then the n-hexane recrystallization under the room temperature condition, to obtain the colorless transparent acicular crystal (12.3g, 65%). Mass spectrum: ES – MS (CH3CN), m/z (%): 266.00 (100) [M + H]+. 2. 6 – dibromo methyl pyridine (B) in acetonitrile electrospray mass spectrum chart of Figure 1.

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, 1195-59-1, 2,6-Pyridinedimethanol.

Reference:
Patent; Nanjing University; WANG, ZHILIN; GENG, ZHIRONG; (25 pag.)CN106518896; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 504-24-5, 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.504-24-5, name is 4-Aminopyridine, molecular formula is C5H6N2, molecular weight is 94.12, as common compound, the synthetic route is as follows.

To a solution of 4-aminopyridine (50.0 g, 531 mmol) in triethylamine/CH2Cl2 (1:1, 200 mL) at 0°C was slowly added a solution of di-t-butyl-dicarbonate (116 g, 531 mmol) in CH2Cl2 (150 mL). The resulting mixture was allowed to warm to it overnight then was concentrated. The crude product was taken up in hot EtOAc, filtered and precipitated with hexanes. The precipitate was collected by filtration, washed with hexanes and dried under vacuum to give 91.0 g (88percent yield) of pure t-butyl carbamate.

The chemical industry reduces the impact on the environment during synthesis 504-24-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PURDUE RESEARCH FOUNDATION; WO2007/61554; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116834-96-9 ,Some common heterocyclic compound, 116834-96-9, molecular formula is C7H7N3, 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 1-(2-chloropyridin-3-yl)ethanone (B-2) (6 g, 38.6 mmol) and hydrazine (85%, 9.1 g, 154.4 mmol) in pyridine (80 mL) was stirred under reflux overnight. The mixture was cooled to room temperature, concentrated, diluted with water (80 mL) and then extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuo. The resulting residue was used for the next step without further purification. MS (m/z): 134 (M+1)+. tert-Btyl 3-methyl-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (B-4)

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. 116834-96-9, 3-Methyl-1H-pyrazolo[3,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; US2012/245178; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214353-79-3, 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 1214353-79-3, name is Methyl 5-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 5-bromo-6-chloropyridine-2-carboxylate (Ark Pharm, 360 mg, 1.4 mmol), copper(I) iodide (19 mg, 0.10 mmol) and dichloro[bis(triphenylphosphonio)]palladate (60 mg, 0.086 mmol) were placed in a vial. The vial was then evacuated and backfilled with nitrogen three times. After this 1,4-dioxane (6.2 mL) and triethylamine (300 L, 2.16 mmol) were added. The reaction was stirred for 5 min. Then (trimethylsilyl)acetylene (244 muIota_,, 1.72 mmol) was added and the resulting reaction mixture was stirred at 60 C for 3 h. After this time the reaction was quenched with water and product was extracted with EtOAc. The combined organic fractions were washed with brine, dried with a2S04 and solvent was evaporated under reduced pressure. The crude product was purified by chromatography on silica gel using Biotage Isolera apparatus to give the sub-title compound (370 mg, 97%). LCMS calc. for C12H15CINO2S1 (M+H)+ m/z = 268.1; found: 268.0.

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 1214353-79-3, Methyl 5-bromo-6-chloropicolinate.

Reference:
Patent; INCYTE CORPORATION; VECHORKIN, Oleg; LI, Yun-Long; ZHU, Wenyu; (232 pag.)WO2016/10897; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 108279-89-6, 2-Chloro-4,6-dimethoxypyridine, 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, 108279-89-6, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Chloro-4,6-dimethoxypyridine

REFERENTIAL EXAMPLE 1 Synthesis of 2-(4,6-dimethoxypyrimidin-2-yloxy)-benzaldehyde (intermediate) After 2.2 g of salicylaldehyde were dissolved in 100 ml of dimethylformamide, 4.0 g of 60% sodium hydride were added little by little. The resulting mixture was stirred at room temperature for a while and, after foaming subsided, 17.5 g of 2-chloro-4,6-dimethoxypyridine were added, followed by heating to 100 C. After the mixture was stirred for 3 hours at the same temperature, dimethylformamide was recovered under reduced pressure. The residue was isolated by column chromatography on a silica gel and then eluted with a 7:3 mixed solvent of n-hexane and ethyl acetate, whereby 14.8 g of the target compound, 2-(4,6-dimethoxypyrimidine-2-yloxy)benzaldehyde, were obtained as crystals (m.p.: 96-98 C.; yield: 56.9%). IR (KBr) cm-1: 2720, 1710. NMR (400 MHz, CDC;3) delta from TMS: 3.80(6H,s), 5.81(1H,s), 7.27(1H,m), 7.36(1H,m), 7.64(1H,m), 7.95(1H,m), 10.24(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,108279-89-6, its application will become more common.

Reference:
Patent; Mitsui Toatsu Chemicals, Inc.; US5178662; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98027-80-6 , The common heterocyclic compound, 98027-80-6, name is 4-Bromo-2,6-dichloropyridine, molecular formula is C5H2BrCl2N, 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.

(2) In a 250 mL three-neck flask, flush with nitrogen.Added 0.02 mol of raw material 4-bromo-2,6-dichloropyridine,150ml DMF, 0.024mol 4-Biphenylboronic acid pinacol ester,0.0002mol palladium acetate, stirring, then add 0.03mol K3PO4 aqueous solution, heated to 130 C, refluxing reaction for 10 hours, sampling point plate,The reaction is complete. Natural cooling, add water,The mixture was filtered and dried in a vacuum ovenThe resulting residue was purified on a silica gel column to give compound intermediate A1;HPLC purity 99.5%, yield 88.3%.

The synthetic route of 98027-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Wang Fang; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (53 pag.)CN107602538; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13143-47-0 ,Some common heterocyclic compound, 13143-47-0, molecular formula is C11H10N2O, 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.

In a 100 mL round-bottomed flask, di(lH-imidazol-1-yl)methanethione (718 mg, 4.03 mmol, Eq:1.5) was combined with CH2Ch (30 mL) to give a colorless solution. 1-(4- Aminophenyl)pyridin-2(1H)-one (500 mg, 2.69 mmol, Eq: 1.00) in CH 2Ch (20 mL) was added dropwise at ooc. The reaction was allowed to warm to room temperature, and allowed to stirovernight. Concentrate the solution, the compound was isolated by column chromatography(Hexanes/EtOAc = 80/20) to give the product 580 mg (95% ). MH+228.9

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. 13143-47-0, 1-(4-Aminophenyl)-1H-pyridin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BERTHEL, Steven Joseph; CHEN, Zhi; CHI, Feng; CHIN, Elbert; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KOCER, Buelent; Mertz, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135471; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem