Category: pyridine-derivatives

Synthetic Route of 886365-46-4, 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 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Crude tert-butyl ((4aRS,11bRS)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (70 mg, 0.165 mmol) was suspended in DMF (2 ml) and sonicated for 1 min. 5-Chloro-3-methylpyridine-2-carboxylic acid (34.0 mg, 0.198 mmol), pyridine (0.04 ml, 0.496 mmol) and HATU (94 mg, 0.248 mmol) were added and resulting suspension was stirred for 45 min at RT. The mixture was diluted with EtOAc (8 ml) and saturated NaHCO3 solution (3 ml). Water was added to dissolve precipitated solids. The organic layer was separated, washed with water and concentrated, and the resulting concentrate/residue was purified by FC on 12 g RediSep Gold column using 10-80% EtOAc in heptane to afford tert-butyl ((4aRS,11bRS)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (76 mg, 0.132 mmol, 80% yield) as white solid.

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 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211532-15-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1211532-15-8, name is 6-Methoxy-5-(trifluoromethyl)nicotinic acid, molecular formula is C8H6F3NO3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

N,O-dimethylhydroxylamine hydrochloride (4.3 g), N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride(9.5 g), and N,N-diisopropylethylamine (30 mL) were added to a mixture of 6-methoxy-5-(trifluoromethyl)nicotinicacid (7.8 g) and methylene chloride (80 mL) under ice-cooling, and then the reaction mixture was stirred at room temperaturefor 17 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were addedethyl acetate and water, followed by stirring for 30 minutes. The mixture was extracted with ethyl acetate, the organiclayer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residuewas purified by silica gel column chromatography (hexane-ethyl acetate) to N,6-dimethoxy-N-methyl-5-(trifluoromethyl)nicotinamide (5.0 g) as an oil.

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 1211532-15-8, 6-Methoxy-5-(trifluoromethyl)nicotinic acid.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; TANAKA, Hiroaki; AKAIWA, Michinori; NEGORO, Kenji; MIHARA, Hisashi; FUJI, Hideyoshi; TAKAMATSU, Hajime; (133 pag.)EP3196200; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51173-05-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 51173-05-8, name is 5-Fluoro-2-hydroxypyridine, molecular formula is C5H4FNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM showed 4-80 and something else (discarded)). The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80. Total: 117.0+3.6+6.23=126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEt A different product was obtained. No desired product in these extracts.

According to the analysis of related databases, 51173-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ueda, Yasutsugu; Connolly, Timothy P.; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao; Chen, Chung-Pin H.; Yeung, Kap-Sun; Zhang, Zhongxing; Leahy, David Kenneth; Pack, Shawn K.; Soundararajan, Nachimuthu; Sirard, Pierre; Levesque, Kathia; Thoraval, Dominique; US2005/209246; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17570-98-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

B) Synthesis of 2- (pyridin-2-yl)-2-bromomethyl-4-hydrox methyl-1, 3-dioxolane cisltrans 316 ml of glycerol were dissolved in 2 1 of toluene and 13.6 g of p- toluenesulfonic acid and 195 g of 2-bromoacetyl-pyridine hydrobromide were added to this solution. The reaction mixture was refluxed for 24 hours, with removal of the water present in the azeotrope. Once the mixture had cooled to ambient temperature, 2 1 of 5% NaHCO3 were added, the two-phase mixture was stirred for 5 minutes and the phases were then separated. The aqueous phase was extracted six times with 600 ml of toluene, the organic phases were combined, dehydrated with Na2S04, and evaporated to dryness under reduced pressure, giving rise to 80 g of (cis/trans)-2-(pyridin-2-yl)-2-bromomethyl-4- hydroxymethyl-1,3-dioxolane (yield 42%).

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 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide.

Reference:
Patent; ITALFARMACO S.P.A.; WO2005/40156; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13958-85-5, 3-Fluoro-5-methylpyridin-4-amine, 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: C6H7FN2, blongs to pyridine-derivatives compound. COA of Formula: C6H7FN2

General procedure: Pd2dba3 (8.25 mg, 9.01 pmol), XantPhos (13.0 mg, 22.5 pmol) and Cs2C03 (110 mg, 0.34 mmol) were dissolved in DMF (2.25 mL) in a sealed tube while N2 was bubbling. 1-49 (42.0 mg, 0.25 mmol) and 1-1 (53.5 mg. 0.23 mmol) were added and the reaction mixture was stirred at room temperature for 10 min. Then, the reaction mixture was heated at 110 C for 20 h. The reaction mixture was cooled to room temperature, filtered through Celite and washed with EtOAc. The solvent was removed under reduced pressure and the crude mixture was purified by reverse phase column chromatography (mobile phase: HCOOH (0.l%)/(MeCN:MeOH, 1 :1), gradient from 95:5 to 63:37) to afford compound 91 (42 mg, 50%) as a white solid.

The synthetic route of 13958-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; LEENAERTS, Joseph, Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; MARTINEZ LAMENCA, Carolina; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (110 pag.)WO2019/243533; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1241752-31-7 ,Some common heterocyclic compound, 1241752-31-7, molecular formula is C8H10BrNO2, 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. Preparation of Compound A mixture of 5-bromo-2-ethoxy-3-methoxypyridine (279 mg, 1.0 mmol), 1-cyclohexenyl boronic acid pinacole ester (250 mg, 1.2 mmol), Pd(PPh3)4 (139 mg, 0.12 mmol) and K2C03 (277 mg, 2.0 mmol) in 1,4- dioxane (3.0 ml) and H20 (1.0 ml) was degassed for 30 min. This mixture was heated to 100 C and stirred for 16 h. The reaction mixture was cooled to room temperature and partitioned between NaHC03 and EtOAc (3x), and washed with NaCl (lx). The organic phase was dried over Na2S04 and was concentrated. The resulting residue was purified by ISCO flash chromatography using 10% EtOAc in hexane to give 551 mg (97%) of the desired product. NMR (300 MHz, CDC13) delta: 7.7 (s, IH), 7.04 (s, IH), 6.0 (m, IH), 4.4 (qt, 2H), 3.84 (s, 3H), 2.36 (m, 2H), 2.18 (m, 2H), 1.78 (m, 2H), 1.7 (m, 2H), 1.4 (t, 3H)

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. 1241752-31-7, 5-Bromo-2-ethoxy-3-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; PARHI, Ajit; SAGONG, Hye Yeon; PATEL, Disha; ARNOLD, Eddy; DAS, Kalyan; VIJAYAN, Suyambu Kesava; WO2014/43252; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, 156094-63-2, blongs to pyridine-derivatives compound. name: 2-(Bromomethyl)-6-methoxypyridine

1.66 g (6.31 mmol) of triphenylphosphine and 685 mg (3.39 mmol) of 2-bromomethyl-6-methoxypyridine were mixed in 10 mL of benzene and heated up to 70 C under nitrogen atmosphere. The mixture was stirred in 25 hours, then cooled to ambient temperature. Theprecipitate was filtered and washed by 10 mL of benzene to give 1.47 g (3.17 mmol, 94 % yield) as awhite powder. The crude was used in the next reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156094-63-2, its application will become more common.

Reference:
Article; Kurihara, Seiya; Nishimura, Yoshinobu; Arai, Tatsuo; Bulletin of the Chemical Society of Japan; vol. 88; 7; (2015); p. 963 – 965;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 578007-66-6, 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. 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-iodo-2-methoxypyridine (50 g, 159 mmol) in toluene (1000 mL) was added phenylmethanethiol (17.8 g, 143 mmol), DIPEA (55.6 mL, 319 mmol), XantPhos (7.37 g, 12.74 mmol). The mixture was degassed with argon for 10 mm then Pd(dba)2 (4.58 g, 7.96 mmol) was added and the reaction mixture was stirred at 70 C for 1 h. The reaction mixture was filtered through celite,washing with EtOAc (200 mL) and the filtrate was concentrated in vacuo. The crude material was purified by normal phase column chromatography on silica eluting with 5% EtOAc in petroleum ether. The appropriate fractions were combined and concentrated in vacuo to afford the title compound (90 g) as a solid.LCMS (Method D) Rt = 2.68 mi [M+H] = 308.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,578007-66-6, 5-Bromo-3-iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (129 pag.)WO2019/20657; (2019); 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 1227384-81-7, name is 2-Bromo-5-(ethylsulfonyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H8BrNO2S

It can be manufactured by the method described in WO 2010/055004250 mg of 2-bromo-5- (ethanesulfonyl) pyridine,Bis (pinacolato) diboron 355 mg,[1,1′-bis (diphenylphosphino) ferrocene]Palladium (II) dichloride dichloromethaneAdduct 49 mg,A mixture of 294 mg of potassium acetate and 3 mL of dimethyl sulfoxide is stirred at 90 C. under a nitrogen atmosphere.After the reaction,The resulting mixture is filtered through Celite.The filtrate is concentrated under reduced pressure,2- (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl) -5- (ethanesulfonyl) pyridine is obtained.

With the rapid development of chemical substances, we look forward to future research findings about 1227384-81-7.

Reference:
Patent; Sumitomo Chemical Chemicals company; Sasayama, Daisuke; Inui, Tomohiko; (102 pag.)JP2019/48845; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55052-27-2 , The common heterocyclic compound, 55052-27-2, name is 6-Chloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5ClN2, 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.

To a solution of 6-chloro-1 H-pyrrolo[2,3-b]pyridine (1.37 g, 8.97 mmol) in DMF (1 00 ml),sodium hydride (60% in paraffin, 1 g, 41 mmol) was added. The solution was stirred for30 min being allowed to warm up from 0 oc to rt. Subsequently, benzenesulfonic acidchloride (1.5 ml, 11.8 mmol) was added dropwise. The suspension was stirred 3 h atroom temperature and hydrolyzed with ice water. The resulting solid was filtered off under25 reduced pressure, washed thoroughly with water (75 ml) and finally with petroleum ether(15 ml). The resulting material was dried at 60 oc and purified by column chromatography (eluent: pure dichloromethane) yielding 856 mg of 1-(benzenesulfonyl)-6-chloropyrrolo[2,3-b]pyridine Xll-20a as a brownish solid.Yield: 32%

The synthetic route of 55052-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem