Month: June 2021

Electric Literature of 144100-07-2, 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. 144100-07-2, name is 2-Bromo-6-fluoropyridine. A new synthetic method of this compound is introduced below.

A mixture of 2-bromo-6-fluoropyridine (225 mg, 1 .280 mmol), (S)-1 -(tetrahydro-2H- pyran-4-yl)ethanamine (212 mg, 1 .280 mmol), DIPEA (331 g, 2.5 mmol) and DMSO (5 mL) was heated in a sealed tube at 90 °C for 18 hrs. The reaction mixture was cooled to room temperature, poured into water (30 mL) and stirred for 20 min. The mixture was extracted with EtOAc (3x 15 mL). The combined organic layers were washed with brine (100 mL) and concentrated to dryness under reduced pressure. The residue was purified by column chromatography [silica gel] providing (S)-6-bromo-N-(1 -(tetrahydro-2H-pyran-4- yl)ethyl)pyridin-2-amine (270 mg). LCMS (m/z): 285.0/286.9 [M+H]+; Rt = 0.91 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,144100-07-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 71493-76-0, 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 71493-76-0, name is 2-Amino-4-methylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Preparation of 2-amino-4-methylnicotinic acid To a 2-L round-bottom flask was placed 2-amino-4-methylpyridine-3-carbonitrile (50 g, 375.51 mmol, 1.00 equiv.) and aqueous potassium hydroxide solution (20%, 700 mL). The resulting solution was stirred at 110 C. in an oil bath overnight and cooled to room temperature. The pH value of the mixture was adjusted to 3 with aqueous HCl solution (2 N). The mixture was concentrated under vacuum. The residue was washed with 2*400 mL of ethanol. The solid was filtered out. The filtrate was concentrated under vacuum to afford 40 g (crude) of 2-amino-4-methylpyridine-3-carboxylic acid as a yellow solid which was directly used in the next step.

According to the analysis of related databases, 71493-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Terrett, Jack Alexander; Chen, Huifen; Constantineau-Forget, Lea; Larouche-Gauthier, Robin; Lepissier, Luce; Beaumier, Francis; Dery, Martin; Grand-Maitre, Chantal; Sturino, Claudio; Volgraf, Matthew; Villemure, Elisia; (138 pag.)US2019/284179; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55717-45-8, 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. 55717-45-8, name is 6-Bromopyridin-3-ol. A new synthetic method of this compound is introduced below.

Example 14a) 5-Benzyloxy-2-bromo-pyridineJTTo a solution of 10.0 g (57.47 mmol) of 2-bromo-5-hydroxypyridine in 400 mL DMF was added 14.75 g (86.21 mmol) of benzyl bromide and 23.82 g (172.4 mmol) of potassium carbonate. The mixture was stirred for 6 h at 600C and overnight at room temperature. The suspension was filtered off and after evaporation of the solvent the residue was chromatogra- phed on silica gel using a dichloromethane/methanol gradient. Yield: 14.82 g (96.7 %).MS (ESIpos): m/z = 264, 266 [M+H]+ 1H-NMR (300MHz, CHLOROFORM-d): delta [ppm]= 5.10 (s, 2H), 7.16 (dd, 1 H), 7.32 – 7.47 (m, 6H), 8.14 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55717-45-8, its application will become more common.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; SCHMITT-WILLICH, Heribert; ROeHN, Ulrike; FRIEBE, Matthias; LEHMANN, Lutz; FITZNER, Ansgar; KRAUSE, Sabine; BROCKSCHNEIDER, Damian; DYRKS, Thomas; THIELE, Andreas; BOeMER, Ulf; MOeNNING, Ursula; HEINRICH, Tobias; WO2010/28776; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 39891-13-9, 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 39891-13-9, name is 2-(6-Chloropyridin-3-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate M-1 was synthesized through the esterification of the carboxylic acid moiety of 2-(6-chloropyridin-3-yl)acetic acid, dimethylation of the carbonyl group at the alpha-position, reduction of the ester moiety with LAH, oxidation of the resultant alcohol moiety, reductive amination with methylamine, protection with a Boc group, amination of the 2-chloropyridine moiety in the presence of a Pd catalyst, and deprotection

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 39891-13-9, 2-(6-Chloropyridin-3-yl)acetic acid.

Reference:
Patent; Teijin Pharma Limited; MIZUNO, Tsuyoshi; SHIMADA, Tomohiro; UNOKI, Gen; EBISAWA, Masaru; TAKEUCHI, Susumu; MINAMIZONO, Kunio; SASAKI, Kosuke; YOKOSAKA, Takuya; IGARASHI, Junji; MARUYAMA, Akinobu; TAKAHASHI, Hiroshi; HORIE, Kyohei; SAKAI, Yuri; (447 pag.)EP3305785; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 99-11-6, 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 99-11-6, name is Citrazinic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of citrazinic acid (15 g) is added phosphorous oxybromide (45 g) and the mixture heated to 140 C. After 14 h the mixture is cooled to 0 C. and MeOH (100 ml) added carefully under vigorous stirring. The mixture is then poured into a cooled (0 C.) aqueous sodium carbonate solution (1M, 500 ml), and chloroform (500 ml) is added. The biphasic mixture is filtered and the organic layer separated. After filtering through charcoal, the solution is concentrated in vacuum. The residue is purified by MPLC (dichloromethane:MeOH 100:3 to 100:6) to yield methyl 2,6-dibromoisonicotinate (13.7 g). HPLC (Rt)=1.62 (method D). To a stirred solution of I5 (2.6 g) in dioxane (30 ml) under argon is added methyl 2,6-dibromoisonicotinate (2.2 g), palladium acetate (167 mg), Xanthphos (432 mg) and Cs2CO3 (5.6 g) and the mixture refluxed for 1 h. The mixture is allowed to cool to room temperature and then added to water and extracted with EtOAc. The organic extracts are washed with brine, dried under Na2SO4, filtered and the solvent evaporated under reduced pressure. The crude product is purified by HPLC (Method E) affording I6 (0.6 g).

According to the analysis of related databases, 99-11-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/264729; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1403257-80-6, 5-Bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide, 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, COA of Formula: C23H30BrN3O3, blongs to pyridine-derivatives compound. COA of Formula: C23H30BrN3O3

11115] To a solution of methyl 3-methyl-2-(3-(6-(4-(4,4, 5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenoxy)hexy- loxy)isoxazol-5-yl)butanoate (200 mg, 0.41 mmol) and 5-bromo-N-((4,6-dimethyl-2-oxo-1 ,2-dihydropyridin-3-yl) methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-meth- ylbenzamide (220 mg, 0.45 mmol) in dioxane (5 mE) and H20 (0.5 mE) was added cesium carbonate (450 mg, 1.38 mmol), Tri-tert-butylphosphine tetrafluoroborate (40 mg, 0.14 mmol), [1,1 ?-l3is(diphenylphosphino)ferrocene]dichlo- ropalladium(II) (46 mg, 0.06 mmol), stirred at 100 C. for 2 hours under nitrogen. The mixture was quenched with water (10 mE) and extracted with dichloromethane methanol (10:1) (10 mEx3), and the combined organic layer was washed with brine (5 mEx2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo and purified by pre-TEC (dichloromethanemethanol=1 5:1) to give methyl 2-(3-(5-(3?-((4,6-dimethyl-2-oxo-1 ,2-dihydropyridin-3-yl)methylcarbamoyl)-5?-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4?-methylbiphenyl-4-yloxy)pentyloxy)isoxazol-5-yl)-3-methylbutanoate (110 mg, 36% yield) as a yellow solid. ECMS (Agilent ECMS 1200-6 120, Column:Waters X-l3ridge C18 (50 mmx4.6 mmx3.5 pm); Column Temperature: 40 C.; Flow Rate: 2.0 mE/mm; Mobile Phase:from 90% [(total 10mM AcONH4) water/CH3CN=900/100 (v/v)] and 10% [(total 10 mM AcONH4) water CH3CN=100/900 (vv)] to 10% [(total 10 mM AcONH4) water/CH3CN=900/100 (v/v)] and 90% [(total 10 mM AcONH4) water/CH3CN=100/900 (v/v)] in 1.6 mm, then under this condition for 2.4 mm, finally changed to 90% [(total 10 mM AcONH4) water/CH3CN=900/100 (v/v)] and 10% [(total 10mM AcONH4) water/CH3CN=1 00/900 (v/v)] in 0.1 mm and under this condition for 0.7 mm). Purity is 76.61%, Rt=1.275 mm.; MS Calcd.: 756.93; MS Found:757.3 [M+H].

The synthetic route of 1403257-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Snyder, Lawrence B.; Wang, Jing; Dong, Hanqing; Qian, Yimin; Berlin, Michael; (513 pag.)US2018/177750; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131803-48-0 ,Some common heterocyclic compound, 131803-48-0, molecular formula is C8H8BrNO2, 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 4-ethyl-N-(3-fluorophenyl)piperazine- l-carboxamide (0.334 g, 1.330 mmol) and sodium hydride (60.00 %, 0.059 g, 1.463 mmol) in tetrahydrofuran (6 mL) was stirred at the room temperature for 30 min, and mixed with methyl 6-(bromomethyl)nicotinate (0.337 g, 1.463 mmol). The reaction mixture was stirred at the same temperature for additional 18 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The bi-phasic mixture was passed through a plastic frit to remove the solid residues and aqueous layer, and the organic layer collected was concentrated in vacuo. The title compound was used without further purification (methyl 6-((4-ethyl-N-(3-fluorophenyl)piperazine- l-carboxamido)methyl)nicotinate, 0.530 g, 99.5 %, brown oil).

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. 131803-48-0, Methyl 6-(bromomethyl)nicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 779345-37-8, 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 779345-37-8, name is 5-Fluoro-2-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 1-azaadamantan-4-ol N-borane complex (1 eq.) and a heteroaryl halide (1.1 eq.) in anhydrous DMF (0.5-1 M) was chilled to between -20 and 0 C and treated with sodium hydride (1.5 equiv; 95%, Aldrich). After 15 minutes, the cooling bath was removed and the mixture was allowed to warm to room temperature. When 1 -azaadamantan-4-ol N-borane complex was consumed as determined by TLC analysis (generally 1-2 hours), the mixture was diluted with water and stirred for 1 hour. The resulting solid product was collected by filtration, washed with water, and dried under reduced pressure to afford the desired product; (4s)-4-(6-Nitropyridin-3-yloxy)-1-azatricyclo[3.3.1.13,7]decane N-borane complex Prepared from the product of Example 10A (419 g, 2.51 mmol) and 5-fluoro-2-nitropyridine (420 mg, 2.9 mmol; see US Patent Appl. 20040209886) according to Method A: 1H NMR (300 MHz, chloroform-D) delta ppm 1.68 – 1.78 (m, 2 H), 2.07 (s, 1 H), 2.20 – 2.35 (m, 4 H), 3.19 – 3 34 (m, 6 H), 4.74 (t, J=3.4 Hz, 1 H), 7.42 (dd, J=9.0, 2.9 Hz, 1 H), 8.26 – 8.31 (m, 2 H). MS (DCI/NH3) m/z= 290 (M+H)+

According to the analysis of related databases, 779345-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/58096; (2008); A2;,
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. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, the common compound, a new synthetic route is introduced below. Safety of 3-(Chloromethyl)pyridine hydrochloride

To a stirring solution of 4-(1-tert-Butoxycarbonyl-2-methyl-propylsulfamoyl)-benzoic acid methyl ester (Compound 1*-884 mg, 2.38 mmol) in dimethylformamide (30 ml) at ambient temperature was added cesium carbonate (10.86 g, 33.34 mmol). Then 3-picolyl chloride hydrochloride (546 mg, 3.33 mmol) was added to the suspension and the reaction mixture was stirred at room temperature for 24 hours by which time TLC (EtOAc/Hexane 1:1) monitoring showed the reaction to be completed. The mixture was evaporated to dryness and the residue was stirred in ethyl acetate (50 ml). The ethyl acetate phase was extracted with water (1×50 ml), dried (MgSO4), filtered and evaporated to afford the crude product as a brown oil. This oil was purified by flash chromatography to furnish the pure product as colourless oil. Yield 800 mg (79.21%).

The synthetic route of 6959-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Storey, Anthony; Davis, Julie; Ricketts, Sally-Ann; Medizabal, Marivi; Cuthbertson, Alan; Arukwe, Joseph; Heywood, Kirsty; Wilson, Ian; Wynn, Duncan; Schafers, Michael; Levkau, Bodu; Wagner, Stefan; Breyholz, Hans-Jorg; Kopka, Klaus; US2007/71670; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 10128-91-3 ,Some common heterocyclic compound, 10128-91-3, molecular formula is C7H7NO3, 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 bottom flask,Add 1.53 g (10 mmol) of 2-hydroxynicotinic acid methyl ester,Potassium carbonate 2.76 g (20 mmol), DMF 50 ml,4-fluorochlorobenzyl 1.73g (12mmol), reacted at 50 C for 8h,The DMF was removed by concentration, poured into water, extracted with dichloromethane and concentrated to give an oil.Then directly add ethanol: water: sodium hydroxide (7:3: 1.5 mol) solution 50ml, reaction at 80 C for 0.5h,Concentrated, the reaction solution was adjusted to pH 5-6 with 1M hydrochloric acid, and a large amount of white solid was precipitated and filtered.White (4-fluorobenzyl)-2-oxo-pyridine-3-carboxylic acid solid

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. 10128-91-3, Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenyang Pharmaceutical University; Ding Huaiwei; Song Hongrui; Xu Yongnan; (10 pag.)CN108239068; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem