Day: June 24, 2021

Application of 13472-59-8 ,Some common heterocyclic compound, 13472-59-8, molecular formula is C6H6BrNO, 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.

Pd2(dba)3 (38.1 mg, 0.042 mmol) and DavePhos (24.6 mg, 0.062 mmol) are added to a N2 purged solution of [7-tert-butyl-5-(4-chloro-3-fluoro-phenyl)furo[3,2-b]pyridin-2-yl]-(2,2- dimethylpiperazin-1-yl)methanone (Hydrochloride salt) (llntermediate D) (100 mg, 0.208 mmol), 3-bromo-2-methoxy-pyridine (39.2 mg, 0.208 mmol) and sodium tert-butoxide (219 iL of 2.0 M,0.437 mmol) in THE. The reaction is stirred in a sealed tube at 100 C for 3 hours. At room temperature, water is added along with dichloromethane and the phases are separated using a phase separator cartridge. The organic phase is then filtrated through a pre-packed Celite pad with DCM and concentrated under vacuum. The crude residue is dissolved in NMP and purified on a Gemini-NX 250-21 column (Isco Combiflash EZ PREP) eluting with 65-100% CH3CN (0.1% Formic Acid)/Water (0.1% Formic Acid) over 30 minutes. Selected fractions are combined and lyophil ized to give [7-tert-butyl-5-(4-chloro-3-fluoro-phenyl)furo [3,2-b] pyridin-2-yl]-[4-(2-methoxy-3-pyridyl)-2,2-dimethyl-piperazin-1-yl]methanone (20.6 mg, 17%) as a yellow solid.ESI-MS m/z calc. 550.2147, found 551.26 (M+1)+; Retention time: 3.37 using Method B. 1H NMR(400 MHz, DMSO-d6) 6 8.18 (dd, J = 11.0, 2.0 Hz, 1H), 8.04 (dd, J = 8.4, 2.0 Hz, 1H), 7.84 (s, 1H),7.77 – 7.69 (m, 2H), 7.56 (s, 1H), 7.22 – 7.15 (m, 1H), 6.93 (dd, J = 7.6, 4.9 Hz, 1H), 3.89 (s, 3H),3.84 – 3.76 (m, 2H), 3.30 – 3.23 (m, 2H), 3.11 (s, 2H), 1.57 (s, 6H), 1.54 (s, 9H).

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. 13472-59-8, 3-Bromo-2-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; LIU, Bingcan; DORICH, Stephane; DE LESELEUC, Mylene; DUPONT-GAUDET, Kristina; JAMES, Clint, Alwyn; VAILLANCOURT, Louis; BEAULIEU, Marc-Andre; STURINO, Claudio; (236 pag.)WO2018/57588; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1134327-98-2, 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. 1134327-98-2, name is Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate. A new synthetic method of this compound is introduced below.

Ethyl 7-hromoimidazo[i,2-ajpvridine-3-carhoxylate (0.100g. 0372 mmoi),aHyipaliadium chloride dimer (2.0 mg, 5.6 imo1), ROCKPHOS (5.2 mg, 0011 mmoi)and cesium carbonate (0.182 g, 0.557 mmol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuumi?Ar), then toluene (2 rnL) was added, followed by the addition of 2-(pyrrolidin-i-yi)ethanol (0064 g, 0.56 mmol), The reaction mixture was degassed again, and stirred at 120 C for 5 Ii The reaction was cooled to rLTo thereaction was added water (1 mL) and LiOl-{ (50 mg). The reaction was heated at 6() Covernight. The solvents were removed. The crude product was purified by preparativeHPLC to afford Intermediate 34 (55 mg, 54 % yield), as a white solid. MS (ESI) in/z:276.0 (M±H). ?H NMR (400MHz. DMSO-d6) d 9.17 (d, J7.5 Hz, 1H), 7.33 (d, J2.4Hz, IH), 7.07 (d, J::::i.8 Hz, IFI), 7.02 (dd, J7.6, 2.5 Hz, IFI), 4.54-4.36 (m, 21-1), 3.86-2.93 (in, 6H), 2.06 (d, J:::90 Hz, 2H), 1.95 – 1.75 (iii. 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1134327-98-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; LADZIATA, Vladimir; DELUCCA, Indawati; PINTO, Donald, J., P.; ORWAT, Michael J.; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; YANG, Wu; SHAW, Scott A.; GLUNZ, Peter W.; PANDA, Manoranjan; (612 pag.)WO2017/123860; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 189449-41-0, (4-Chloropyridin-3-yl)methanol, 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, 189449-41-0, blongs to pyridine-derivatives compound. Safety of (4-Chloropyridin-3-yl)methanol

Example 21 3-chloromethyl-4-chloropyridine hydrochloride Thionyl chloride (0.714 mL, 9.78 mmol) was added at room temperature to dry DMF (7 mL). After 30 min the above solution was cannulated into the solution of 3-hydroxymethyl-4-chloropyridine (700 mg, 4.89 mmol) in DMF (3 mL). After 45 min, the product was precipitated by addition of dry ether (100 ml), washed with ether, and dried in vacuum to yield 813 mg (84percent) of the title compound. 1H NMR (CD3 OD) delta 5.00 (s, 2H), 8.31 (d, 1H, J=5), 8.99 (d, 1H, J=5), 9.18 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189449-41-0, its application will become more common.

Reference:
Patent; Microcide Pharmaceuticals, Inc.; US6066630; (2000); A;; ; Patent; Microcide Pharmaceuticals, Inc.; US6087355; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 129421-32-5, 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 129421-32-5 as follows.

To a stirred solution of 2,3-dihydro-[l,4]dioxino[2,3-b]pyridine (2000 mg; 14.3 mmol) in THF (15 mL) was added n-butyllithium solution, 1.6N in n-Hex (17.9 mL; 28.6 mmol) at -78 C. After 0.5 h, a solution of 1 ,2-dibromotetrafluoroethane (1.74 mL; 14.3 mmol) in THF (5 mL) was added dropwise over 5 min at -78 C. The reaction mixture was further stirred for 0.5 h. A saturated aqueous solution of NH4C1 (10 mL) was cautiously added, followed by the addition of EA (50 mL). The organic layer was successively washed with water and brine, dried over Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel; 2-methylpentane : EA; 7:3; v/v) to afford 8-bromo-2,3- dihydro-[l,4]dioxino[2,3-b]pyridine (1000 mg) as a white solid. (0872) MS m/z (+ESI): 216.1, 218.1 [M+H]+. (0873) ‘H-NMR (400 MHz, DMSO-i delta ppm: 7.61 (d, J = 5.2 Hz, 1H), 7.24 (d, J = 5.2 Hz, 1H), 4.45 – 4.42 (m, 2H), 4.36 – 4.34 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,129421-32-5, its application will become more common.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; RICHALET, Florian; WEILER, Sven; EL SHEMERLY, Mahmoud; LANE, Heidi; (131 pag.)WO2019/72978; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14254-57-0, 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.14254-57-0, name is Isonicotinoyl chloride, molecular formula is C6H4ClNO, molecular weight is 141.5551, as common compound, the synthetic route is as follows.

To a suspension of indigo (1.0 g, 3.8 mmol) in anhydrous ethyl acetate (50m1) containing sodium acetate (0.8 g, 9.5mmol) and zinc (2.49 g, 38 mmol) was added isonicotinoyl chloride (2.0 g, 11.4 mmol). The reaction mixture was allowed to stir for 30 mins at 40C. The suspension was allowed to cool to room temperature and then concentrated to dryness. The residue was extracted with hot acetone. The crude material was purified using flash column chromatography eluting with 20% ethyl acetate: pet ether. The product was isolated as a pale yellow solid and was confirmed by ?H NMR to be the di-substituted product, Compound 22(0.4g, 22%). Mw, C28H18N404, 474.47; ?H NMR (400 MHz, DMSO) oe 11.36 (s, 1H), 11.12 (s, 1H),7.59 (d, J 8.0 Hz, 1H), 7.50 (dd, J 8.1, 0.9 Hz, 1H), 7.46 – 7.41 (d, 8.1 Hz, 1H), 7.36 (d, J=8.1 Hz, 1H), 7.16 (dddd, J= 12.9, 8.2, 7.0, 1.2 Hz, 2H), 7.05 (ddt, J 8.1, 7.0, 1.1 Hz, 2H), 6.84(dd,J= 2.1, 0.8 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 14254-57-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VF JEANSWEAR LP; PUVVADA, Sudhakar; SCHEER, Dennis; HOERTZ, Paul, Gerard; (146 pag.)WO2019/126469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-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, Product Details of 74420-15-8, blongs to pyridine-derivatives compound. Product Details of 74420-15-8

[0383] Example lb: 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (7a) [0384] 3-bromo-lH-pyrrolo[2,3-b]pyridine (6a) (10.7 kg, 54.3 moles) was added to 94.3 kg of THF in a 200 L glass-lined reactor. The solid was dissolved completely by stirring. After the mixture was cooled to about 10-15 C, NaH (3.4 kg, 85 moles) was added in portions (about 200-250 g each portion) every 3 to 5 minutes while venting any H2 gas released by the reaction. After the addition of NaH, the mixture was stirred for one hour while maintaining the temperature of about 10-20 C. 4-methylbenzenesulfonylchloride (12.4 kg, 65.0 moles) was added at a rate of 0.5 kg/10 minutes at about 10-20 C. After the addition was complete, the temperature was maintained at about 10-20 C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-lH-pyrrolo[2,3- bjpyridine (6a) was less than 1% (after about 1.5 hours). [0385] The reaction was quenched with water (10.7 kg) while maintaining the temperature below 20 C. Dichloromethane (41.3 kg) was added to the mixture. Then 3% HC1 (42.8 kg) was added into the mixture while maintaining the temperature below 25 C. After the addition, the phases were allowed to separate for 0.5 hour. The aqueous phase was extracted twice with dichloromethane. During each extraction, the mixture was stirred for 15 minutes and then held for 15 minutes. All the organic phases were combined. The combined organic phases were washed with 3% HC1 (33.4 kg) and water (40 kg). During each wash, the mixture was stirred for 15 minutes and then held for 30 minutes. [0386] The mixture was transferred into a 50 L vacuum filter and filtered through silica gel (3 kg). The cake was washed with dichloromethane (35 kg) twice. The filtrate and washings were combined. The organic phase was concentrated below 40 C under vacuum of a pressure less than -0.085 MPa until 10 L mixture remained. Petroleum ether (9kg) was added into the residue. The mixture was stirred until it was homogeneous. The slurry was transferred into a 50 L vacuum filter and filtered. The cake was washed with petroleum ether (9 kg). A light brown solid resulted (17 kg, 99.7% purity as measured by HPLC analysis (method A), 94% yield of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (7a)).

The synthetic route of 74420-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; TANOURY, Gerald, J.; JUNG, Young, Chun; MAGDZIAK, Derek; LOOKER, Adam; WO2013/6634; (2013); A2;,
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 4214-73-7, name is 2-Amino-5-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Amino-5-cyanopyridine

To a solution of compound 53.9 (10 g, 83.95 mmol, 1 eq) in THF (150 mL) wasadded LAH (6.37 g, 167.90 mmol, 2 eq) at 0C. The mixture was stirred at 0C for 1.5 hours.The reaction mixture was quenched by addition saturated sodium sulfate at 0 C and added100 ml H20 then extracted with ethyl acetate (100 mL x 3). The combined organic layerswere washed with saturated brines (30 mL x 1), dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressure to give the product compound 53.8 (7.50 g, 61.42mmol, 73.16% yield) as a yellow oil. LCMS (ESI): m/z: [M + H] called for C6H6N20: 123;found 123; RT=0.099 mm.

With the rapid development of chemical substances, we look forward to future research findings about 4214-73-7.

Reference:
Patent; CORTEXYME, INC.; LYNCH, Casey C.; KONRADI, Andrei; GALEMMO, JR., Robert A.; (218 pag.)WO2018/209132; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128071-98-7, Adding some certain compound to certain chemical reactions, such as: 128071-98-7, name is 4-Bromo-2-fluoropyridine,molecular formula is C5H3BrFN, 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 128071-98-7.

Step 1: Preparation ofl-(4-bromopyridin-2-yl)cyclopropanecarbonitrile.LiHIVIDS (1 M in toluene, 17.6 mL, 17.6 mmol, 3.1 eq) was added dropwise to a cold (-5C) mixture of 4-bromo- 2-fluoropyridine (1 g, 5.7 mmol), cyclopanecarbonitrile (1.25 mL, 17 mmol, 3 eq) and4A MS in toluene (20 mL). The reaction mixture was allowed to warm to room temperature and stirred for 16 hr. After it was poured into water, the mixture was filtered. The filtrate was diluted with EtOAc and 1120, and extracted with EtOAc. The organic phase was washed with water and brine, dried over anhydrous Na2504, and concentrated. The residue was purified by column chromatography using PE/EtOAc (9:1) as eluent to give the desired product. LC-MS: m/z 223.0 (M+H).

According to the analysis of related databases, 128071-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; ZAHLER, Robert; CAI, Zhenwei; ZHOU, Ding; WO2015/3640; (2015); 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. 873107-98-3, name is 5-Iodo-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-Iodo-2-(trifluoromethyl)pyridine

In a microwave vial, 3-ethylsulfanyl-2-(1 H-1 ,2,4-triazol-3-yl)-5-(trifluoromethyl)pyridine (274 mg, 1 .0 mmol) and 5-iodo-2-(trifluoromethyl)pyridine (409 mg, 1 .50 mmol) were dissolved in dry DMF (3 ml) and potassium carbonate (276 mg, 2.00 mmol) was added. The vial was closed and the mixture was heated in the microwave at 140C for 6 h. The reaction mixture was partitioned between EtOAc and brine/water (1/1 ). After washing and separation, the organic layer was washed with water/brine (1/1 ), dried over sodium sulfate and concentrated. The crude product was purified over silica by flash column chromatography (5 to 75% gradient of EtOAc in heptane). The fractions containing product were combined and concentrated. The crude product was again purified over silica by flash column chromatography (0 to 2.5% gradient of MeOH in CH2CI2) to afford the compound P1 .1 (221 mg) as a solid, mp 174.5-175.5C. LCMS (method 2): 420 (M+H)+, retention time 3.85 min. H-NMR (CDCI3, ppm) 1 .45 (3H), 3.07 (2H), 7.91 (1 H), 7.93 (1 H), 8.38 (1 H), 8.79 (1 H), 8.87 (1 H), 9.26 (1 H).

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, 873107-98-3, 5-Iodo-2-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; TITULAER, Ruud; EMERY, Daniel; EDMUNDS, Andrew; STOLLER, Andre; JUNG, Pierre Joseph Marcel; JEANGUENAT, Andre; BUCHHOLZ, Anke; (82 pag.)WO2016/12395; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17228-64-7 ,Some common heterocyclic compound, 17228-64-7, molecular formula is C6H6ClNO, 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.

General procedure: Under Nitrogen, to a 10 mL Schlenk flask equipped with a magnetic bar, potassium hydroxide (4.5 mmol, 252 mg), phenyl boronic acid (3.15 mmol), and aryl chlorides (3 mmol) (if liquid, was injected through the septum later), catalyst 3 (0.05 mol% catalyst loading, 1 mg) were added in turn, followed by addition of 2-propanol (5 mL) and H2O (0.5 mL). The mixture was then stirred at 80 for 2 h. It was also monitored by gas chromatography. Water was added to the reaction mixture, which was extracted by ethyl acetate, dried over anhydrous Na2SO4, and the solvent was evaporated in vacuum. When necessary the product was purified by flash chromatography.

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. 17228-64-7, 2-Chloro-6-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shen, An; Hu, Yu-Cai; Liu, Ting-Ting; Ni, Chen; Luo, Yong; Cao, Yu-Cai; Tetrahedron Letters; vol. 57; 19; (2016); p. 2055 – 2058;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem