Day: August 25, 2021

Adding a certain compound to certain chemical reactions, such as: 677728-92-6, 2-Fluoropyridine-5-carbaldehyde, 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, 677728-92-6, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Fluoropyridine-5-carbaldehyde

EXAMPLE 234. 5-(l,3-DIOXOLAN-2-YL)-2-FLUORO-3-(4,4,5,5-TETRAMETHYL-l,3,2- DIOXABOROLAN-2-YL)PYRIDINESTEP 1: 5-(l,3-DIOXOLAN-2-YL)-2-FLUOROPYRIDINE[00611 ] 6-Fluoronicotinaldehyde (21.96 g, 176 mmol) was suspended in toluene (340 mL) and ethylene glycol (10.4 mL, 186 mmol) and p-toluenesulfonic acid (Acros, 15% in acetic acid, 1.10 mL) were added. The flask was fitted with a Dean-Stark head and a reflux condenser, and placed in a preheated oil bath (120 0C) and the reaction was stirred. After 45 minutes, the reaction was cooled to room temperature. The reaction was diluted with saturated sodium bicarbonate (50 mL), water (150 mL) and EtOAc (150 mL). The layers were separated and the aqueous phase was extracted with EtOAc. The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (600 mL fritted filter with about 3 inches of silica gel; DCM to 100: 1 to 50: 1 DCM / MeOH to 40: 1 DCM / MeOH) to give 19.055 g of 5-(l,3-dioxolan-2-yl)-2-fluoropyridine. m/z (ESI, +ve ion) 170 (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,677728-92-6, its application will become more common.

Reference:
Patent; AMGEN INC.; ANDREWS, Kristin; BO, Yunxin, Y.; BOOKER, Shon; CEE, Victor, J.; D’ANGELO, Noel; HERBERICH, Bradley, J.; HONG, Fang-Tsao; JACKSON, Claire, L., M.; LANMAN, Brian, A.; LIAO, Hongyu; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; PETTUS, Liping, H.; REED, Anthony, B.; SMITH, Adrian, L.; TADESSE, Seifu; TAMAYO, Nuria, A.; WU, Bin; WURZ, Ryan; YANG, Kevin; WO2010/126895; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1111637-68-3, 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 1111637-68-3 as follows.

To a solution of 5-bromo-3-fluoro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 4.65mmol) in 1,4-dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.77 g, 6.98 mmol), potassium acetate (1.37 g, 13.95 mmol) and l, l’-bis(diphenylphosphino)ferrocene-palladium(n)dichloride (340 mg, 0.46mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 2 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether ) affording 3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (240 mg, 20%): NMR (400 MHz, Chloroform-d) delta 11.44 (m, 1H), 8.73 (d, 7= 1.6 Hz, 1H), 8.46 (d, 7= 1.2 Hz, 1H), 7.10 (m, 1H), 1.39 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-68-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 62150-45-2, 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 62150-45-2, name is 4-Bromopyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

e) C- (4-Bromopyridin-2-vl) methylamine; A solution of 18.70 g 4-bromopyridine-2-carbonitrile [62150-45-2] in 200 mi of tetrahydrofuran is admixed under argon dropwise with 500 ml of 1 M borane-tetrahydrofuran complex solution. The reaction solution is subsequently left to stand at room temperature for 16 hours. The reaction solution is cooled to 0C, admixed dropwise with 500 ml of 2M HCI and heated to reflux for 30 minutes. The reaction solution is cooled to room temperature, basified with 2M NaOH, saturated with sodium chloride and extracted with tetrahydrofuran (3 x 300 ml). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (Si02 60F).

According to the analysis of related databases, 62150-45-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90305; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7340-22-9, Adding some certain compound to certain chemical reactions, such as: 7340-22-9, name is 3-(2-pyridyl)acrylicacid,molecular formula is C8H7NO2, 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 7340-22-9.

General procedure: Add the acid (III) to the dried 10 mL round bottom flask and add the solvent to dichloromethane.Stirring was started, then 1.1 eq of oxalyl chloride was added to 0.1 eq of N,N-dimethylformamide, and the reaction was treated after 2 h.Concentration in vacuo gave the compound acid chloride (IV). Compound 2 was dissolved in DCM and 1.5 eq of triethylamine (TEA) was added.After stirring for 1-2 min, add 1.2 eq of acid chloride and stir at room temperature for 1 h.The reaction was completely detected by TLC, quenched with distilled water and extracted three times with DCM.The organic phase was combined, dried over anhydrous Na2SO4, filtered, and then evaporated.(Petroleum ether / ethyl acetate) gave the title compound 37-42 (white amorphous solid).

According to the analysis of related databases, 7340-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nankai University; Chinese Academy Of Medical Sciences Xueyebing Hospital (Xueyexue Institute); Tianjin Shang De Yaoyuan Technology Co., Ltd.; Zhang Quan; Chen Yue; Gao Yingdai; Ding Yahui; Li Ye; Lian Lihui; Ge Weizhi; (22 pag.)CN109206389; (2019); 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. 1480-87-1, name is 2-Fluoro-3-nitropyridine. A new synthetic method of this compound is introduced below., name: 2-Fluoro-3-nitropyridine

1.5 g of 2-fluoro-3-nitropyridine,1.5 g of tert-butyl trans-(4-aminocyclohexyl)carbamate was dissolved in acetonitrile.4 mL of triethylamine was added and reacted at 85 C for 12 hours.The reaction solution was cooled to room temperature and concentrated under reduced pressure.Adding an aqueous solution of citric acid, heating and stirring at 30 C, and vacuum filtration.The filter cake was washed with a small amount of diethyl ether to give an orange solid, which was intermediate XI.The yield was 65%.

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, 1480-87-1, 2-Fluoro-3-nitropyridine.

Reference:
Patent; Sichuan University; Yang Shengyong; Li Linli; (36 pag.)CN109180702; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 78686-79-0, 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. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate. A new synthetic method of this compound is introduced below.

Compounds are represented in generic form, with sub stituents as noted in compound descriptions elsewhere herein. A more specific example is set forth below. In one aspect, ethers of type 6.7 can be prepared beginning with the commercially available 5-bromo-2-chloronicotinic acid, which is converted to the corresponding ester by reaction with methanol in the presence of an acid such as hydrochloric acid to yield compound 6.2. Alkylation to provide compound 6.3 is accomplished by use of a Suzuki cross coupling reaction using potassium allyltrifluoroborate in the presence of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II). Reaction with 4-methoxybenzylamine affords compound 6.4. A cross-coupling reaction between compound 6.4 and benzyl alcohol in the presence of CuI, Cs2CO3, and a diamine ligand yields the aryl ether, compound 6.5. The p-methoxybenzyl protecting group is removed using cerium(IV) ammonium nitrate (CAN), followed by reduction of the carbonyl using lithium aluminum hydride. The amide, compound 6.7, is formed by reaction of the 3-(benzyloxy)-5,6,7,8-tetrahydro-1,6-naphthyridine, formed in the previous step, with benzoyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78686-79-0, its application will become more common.

Reference:
Patent; Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Dawson, Eric S.; US2012/178776; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74784-70-6, 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 74784-70-6 as follows.

To a de-gassed mixture of 3- [3- (trifluoromethyl) pyridin-2-yl] pyrido [2,3-b] pyrazin-8- amine (72 mg, 0.25 MMOL), cesium carbonate (162 mg, 0.5 mmol), 2-amino-trifluoromethyl pyridine (45 mg, 0.25 mmol) in dioxane (5 mL) under nitrogen, add PD2DBA3 (11 mg) and xantphos (7 MG). Stir the mixture AT 100C for 3 hours, cool, add water (10 mL) and extract with EtOAc. Dry over NA2SO4, concentrate under vacuum. Purify by chromatography eluting with DICHLOROMETHANE/METHANOL/AMMONIUM hydroxide mixture to give the title compound. MS 437 (M + 1).’H NMR 6 (CDCI3) 9.42 (1H, s), 9.28 (1H, s), 9.11 (1H, d), 8.95 (1H, d), 8. 90 (IH, d), 8.72 (1H, s), 8.25 (1H, d), 7.89 (1H, d), 7.61 (1H, dd), 7.13 (1H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74784-70-6, its application will become more common.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/7652; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1289093-31-7, 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. 1289093-31-7, name is 5-Bromo-3-chloro-2-isobutoxypyridine. A new synthetic method of this compound is introduced below.

Preparation 32: 3-Chloro-2-isobutoxy-5-(4 A5,5-tetramethyl-H ,3,21dioxaborolan-2- -pyridine; Method (i):; To a dry flask was added 5-bromo-3-chloro-2-isobutoxy-pyridine [preparation 30] (825mg, 3.12mmol), KOAc (918mg, 9.35mmol), bis- pinocolatodiboronate (989mg, 3.90mmol) and Pd(dppf)2CI2 (127mg, 0.156mmol) followed by DMF (10ml). The mixture was degassed twice by evacuating and filling with nitrogen and heated at 80C for 6 hours under nitrogen. The reaction mixture was partitioned between EtOAc (30ml) and water (30ml), and the organics washed with brine (20ml), dried over MgS04, filtered and concentrated in vacuo. Purification by column chromatography (ISCO Companion, 40g, heptane – 30% EtOAc:heptane) gave the desired product as a colourless oil (227mg).1 H NM (400 MHz, CDCI3) delta ppm 1 .04 (d, J=6.64 Hz, 6 H) 1 .34 (s, 12 H) 2.09 – 2.21 (m, 1 H) 4.18 (d, J=6.64 Hz, 2 H) 7.97 (d, J=1 .56 Hz, 1 H) 8.37 (d, J=1 .56 Hz, 1 H) impurities present

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1289093-31-7, 5-Bromo-3-chloro-2-isobutoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; BELL, Andrew Simon; DE GROOT, Marcel John; LEWTHWAITE, Russell Andrew; MARSH, Ian Roger; SCIAMMETTA, Nunzio; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/95781; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72587-15-6, 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 72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Production Method of 2-Methyl-1-phenylpropan-2-yl 3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate Sodium hydride (240 mg, 3 Eq) was dissolved in DMA (dimethylacetamide) (2 mL). Under ice cooling, a DMA solution (2 mL) of 2-methyl-1-phenylpropan-2-yl 3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate (895 mg, 2 mmol) was slowly added to the solution, and the mixture was stirred for 30 minutes. After that, a DMA solution (2 mL) of 2-chloro-3-nitro-5-trifluoromethylpyridine (454 mg, 1 Eq) was slowly added, and the mixture was stirred at room temperature for 4.5 hours. Water and 3 N hydrochloric acid were added to the reaction mixture, and ethyl acetate extraction was performed. The organic layer was concentrated and the residue was subjected to column chromatography to give the desired compound, i.e., 2-methyl-1-phenylpropan-2-yl 3-(3-ethylthio-5-trifluoromethylpyridin-2-yl)-2-(3-nitro-5-trifluoromethylpyridin-2-yl)-3-oxo-propionate (653 mg, containing about 20% nitropyridine (starting material)).

According to the analysis of related databases, 72587-15-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; Yonemura, Ikki; Sano, Yusuke; Suwa, Akiyuki; Fujie, Shunpei; US2018/352811; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 886365-28-2, name is Methyl 5-bromo-2-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 886365-28-2

Methyl 5-bromo-2-chloro isonicotinate (30 g, 120 mmol) was dissolved in 1,4-dioxane (300 mL), and 3,5-dimethoxyphenylacetylene (20.4 g, 120 mmol), CuI (2.28 g, 12 mmol), Pd(dppf)Cl2 (4.2 g, 6 mmol) and Et3N (12.0 g, 120 mmol) were added, and the mixture was heated to 60 C. under N2, for 6 h. The reaction was complete, and the mixture was filtered and concentrated. The crude product was separated by silica gel column chromatography (DCM:PE=20:1) to obtain compound methyl 2-chloro-5-((3,5-dimethoxyphenyl)ethynyl)isonicotinate (22 g, yield: 55%). MS (ESI): m/z 332.1 [M+1]+.

With the rapid development of chemical substances, we look forward to future research findings about 886365-28-2.

Reference:
Patent; Abbisko Therapeutics Co., Ltd.; YANG, Fei; DENG, Haibing; YING, Haiyan; YU, Hongping; CHEN, Zhui; XU, Yaochang; (604 pag.)US2019/270742; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem