Category: pyridine-derivatives

Reference of 13466-43-8, 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. 13466-43-8, name is 3-Bromopyridin-2(1H)-one, molecular formula is C5H4BrNO, 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.

In a sealed tube, a suspension of 400 mg (1.09 mmol) of tert-butylN-[1-[(4-acetylenyl-6- isoquinolyl)methyl] -4-piperidyl]carbamate, 240 mg( 1.38 mmol) of 3 -bromo-2-hydroxypyridine, 77 mg(0.1 1 mmol) of Pd(PPh3)2C12 and 535 mg (1.64 mmol) of Cs2CO3 in 10 mL of DMF under an inert atmo sphere was stirred at 110C for 16 h. The mixture was extracted with EA/H20. The organic layerwashed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to give the crude product,which was purified via silica gel (pure EA) to give 107 mg of product as a light yellow semisolid.MS (+ESI): 459.3 [M+H].?H NMR (400 MHz, DMSO-d6+D20) ppm: 9.35 (s, 1H), 8.88 (s, 1H), 8.36 (d, J = 4.8 Hz, 1H), 8.30 (s, 1H), 8.22-8.20 (m, 2H), 7.65 (d, J = 8.0 Hz, 1H), 7.56 (s, 1H), 7.44 (m, 1H), 3.66 (s, 2H), 3.19 (m, 1H),2.73 (m, 2H), 2.05 (m, 2H), 1.66 (m, 2H), 1.37 (m, 2H), 1.32 (s, 9H).

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 13466-43-8, 3-Bromopyridin-2(1H)-one.

Reference:
Patent; BASILEA PHARMACEUTICA AG; POHLMANN, Jens; STIEGER, Martin; REINELT, Stefan; LANE, Heidi; (286 pag.)WO2016/128465; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1210419-26-3, Adding some certain compound to certain chemical reactions, such as: 1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate,molecular formula is C7H5BrFNO2, 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 1210419-26-3.

Synthesis of methyl 6-(2,6-difluoro-4-(4-hvdroxytetrahvdro-2H-pyran-4-yl)phenyl)-5- fluoropicolinate Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.0 equiv.) and 4-(3,5-difluoro-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H- pyran-4-ol (1.8 equiv.) at 100 C for 20 min in microwave to give methyl 6-(2,6-difluoro- 4-(4-hydroxytetrahydro-2H-pyran-4-yl)phenyl)-5-fluoropicolinate. LC/MS = 368.0 (MH+), R, = 0.75 min.

According to the analysis of related databases, 1210419-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BURGER, Matthew; NISHIGUCHI, Gisele; RICO, Alice; SIMMONS, Robert Lowell; TAMEZ, JR., Victoriano; TANNER, Huw; WAN, Lifeng; WO2014/33631; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 67625-37-0, 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 67625-37-0, name is Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 86 6-Aminoimidazo[1,2-a]pyridine-2-carboxamide To a solution of ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate (Preparation 87, 2 g, 0.0074 mol) in MeOH (30 mL) was added ammonia (3 g, 0.044 mol) and the reaction was heated to 100 C. in a sealed vessel for 24 hours. The reaction was cooled and concentrated in vacuo to afford the title compound (1.9 g, 90%).

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 67625-37-0, Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate.

Reference:
Patent; PFIZER INC.; Fensome, Andrew; Gopalsamy, Ariamala; Gerstenberger, Brian S.; Efremov, Ivan Viktorovich; Wan, Zhao-Kui; Pierce, Betsy; Telliez, Jean-Baptiste; Trujillo, John I.; Zhang, Liying; Xing, Li; (104 pag.)US2016/52930; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 131747-61-0, (2-(Trifluoromethyl)pyridin-4-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, 131747-61-0, blongs to pyridine-derivatives compound. Recommanded Product: (2-(Trifluoromethyl)pyridin-4-yl)methanol

534 tert-Butyl N-[(3-hydroxyphenyl)methyl]carbamate (0.18 g, 1.0 mmol), E-1 (0.22 g, 1.0 mmol) and 13 triphenylphosphine (0.39 g, 1.5 mmol) were dissolved in 12 dichloromethane (3 mL), 236diisopropyl azodicarboxylate (0.32 mL, 1.5 mmol) was added, and the mixture was stirred at roomtemperature for 1 hr. The reaction mixture was concentrated under reduced pressure and the obtained residuewas purified by silica gel column chromatography (hexane/ethyl acetate). To the obtained compound wasadded 4 mol/L 114 hydrochloric acid (1,4-dioxane solution, 3 mL), and the mixture was stirred at roomtemperature for 1 hr, and concentrated under reduced pressure to give the 535 title compound ( 0.13 g ,0.40 mmol, 40%) MS (ESI) m/z 283 (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,131747-61-0, its application will become more common.

Reference:
Patent; EA PHARMA CO., LTD.; KOBAYASHI, Kaori; SUZUKI, Tamotsu; KAWAHIRA, Mizuki; FUJII, Tomohiro; SUGIKI, Masayuki; OHSUMI, Koji; OKUZUMI, Tatsuya; (285 pag.)US2016/332999; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 126325-47-1 ,Some common heterocyclic compound, 126325-47-1, molecular formula is C6H7BrN2, 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.

Example 7 6-Methanesulfonyl-2-methyl-pyridin-3-ylamine A 5-L 4-neck flask equipped with a thermocouple controller, an overhead mechanical stirrer, a condenser, and a nitrogen inlet/outlet was charged with sodium methanesulfinate (568 g, 4.73 mol), copper(1 ) thfluoromethanesulfonate benzene complex (70 g, 0.139 mol), N, N’- dimethylethylenediamine (12.3 g, 0.139 mol), and bromo-amine (260 g, 1.39 mol) in DMSO (800 ml_). The resulting mixture was heated to 1500C for 1 hour. The resulting mixture was then diluted with H2O (1.5 L) and extracted with EtOAc (6 x 2 L). The combined organic layers were evaporated to dryness to yield a residue. The residue was purified via ISCO Prep chromatography system. The product containing fractions were combined and evaporated to dryness. The resulting product (residue) was placed in vacuum oven at 400C for 18 hours to yield 6-methanesulfonyl-2-methyl-pyhdin-3-ylamine as a as a brownish solid. MS: 187.1 MW+H+

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. 126325-47-1, 6-Bromo-2-methylpyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LI, Xun; WELLS, Ken; BRANUM, Shawn; DAMON, Sandra; WO2010/135506; (2010); 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 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 73027-79-9

Intermediate 4.4 To a suspension of NaH (5.2 g, 130 mmol) in THF (100 mL) is added MeOH (4.2 g, 130 mmol) at 0 C. After stirring at r.t. for 30 min, a solution of 4,6-dichloronicotinic acid (10 g, 52.9 mmol, U.S. Pat. 2005049419.) in THF (100 mL) is added dropwise at 0 C. The resulting mixture is stirred at room temperature overnight. After adding water, the mixture is washed with ether. The aqueous phase is acidified with KHSO4 and then extracted with ether. The organic phase is washed with brine and dried over MgSO4. Concentration under reduced pressure gives Intermediate 4.4: colorless crystal, ES-MS: M+H=188: CtRet=1.80 min.

With the rapid development of chemical substances, we look forward to future research findings about 73027-79-9.

Reference:
Patent; Yokokawa, Fumiaki; Ehara, Takeru; Kawakami, Shimpei; Irie, Osamu; Suzuki, Masaki; Hitomi, Yuku; Toyao, Atsushi; US2008/319018; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 152460-10-1 , The common heterocyclic compound, 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine, molecular formula is C16H15N5, 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.

Embodiment 3 In a 5000 ml dried 4-neck flask, 3000 ml toluene,277 g 4-methyl-N-3-(4-pyridin-3-yl-pyrimidin-2-yl)-1,3-benzenediamine, and 450 g 4-(4-methyl-piperazin-1-methyl)-benzoic acid benzyl ester were added. After it was stirred to dissolve, 200 g sodium ethoxide was then added. The mixture was heated to 50 C. for reaction overnight until the reaction was detected to be complete, and then concentrated to remove toluene. The residue solid was washed with water and dried, thus 445 g Imatinib was obtained, and the yield was 90.0%. The data of spectrum is the same as above.

The synthetic route of 152460-10-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shen, Xin; He, Xiao; Yang, Jidong; Wu, Shaohong; Zhan, Huaxing; US2013/41149; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.112197-15-6, name is 3-Iodo-2-methoxypyridine, molecular formula is C6H6INO, molecular weight is 235.02, as common compound, the synthetic route is as follows.Recommanded Product: 112197-15-6

To a stirred, cooled (0C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2*TMEDA (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0C before introduction of the substrate (1.0 mmol) at 0-10C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solution of Na2S2O3 (4 mL) and extraction with AcOEt (3×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. To the crude iodide were added Cs2CO3 (0.65 g, 2.0 mmol), Cu powder (13 mg, 0.20 mmol), the azole (1.5 mmol) and MeCN (5 mL) and the resulting mixture was heated under reflux for 24 h. Filtration over Celite, washing with AcOEt, removal of the solvent and purification by chromatography on silica gel (the eluent is given in the product description) led to the compound described below. 2-Methoxy-3-(1-pyrazolyl)pyridine (1c). The general procedure 1 using 2-methoxypyridine (1a, 0.11 mL) and pyrazole (0.10 mL) gave 1c (eluent: heptane-AcOEt 80:20) in 32% yield as a pale yellow oil: IR (ATR): 752, 795, 933, 1016, 1045, 1105, 1189, 1251, 1304, 1394, 1415, 1471, 1521, 1593, 1736, 2956 cm-1; 1H NMR (CDCl3) d 4.04 (s, 3H), 6.42 (dd, 1H, J 2.5 and 1.8 Hz), 7.00 (dd, 1H,J 7.6 and 5.0 Hz), 7.70 (d, 1H, J 1.4 Hz), 8.07-8.13 (m, 2H), 8.21 (dd,1H, J 2.5 and 0.5 Hz); 13C NMR (CDCl3) d 54.0 (CH3), 106.8 (CH),117.4 (CH), 124.8 (C), 131.3 (CH), 131.8 (CH), 140.8 (CH), 144.3 (CH),154.9 (C); HRMS (ESI): calcd for C9H9N3NaO ([M+Na]) 198.0643, found 198.0641.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112197-15-6, 3-Iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Article; Hedidi, Madani; Erb, William; Bentabed-Ababsa, Ghenia; Chevallier, Floris; Picot, Laurent; Thiery, Valerie; Bach, Stephane; Ruchaud, Sandrine; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Tetrahedron; vol. 72; 41; (2016); p. 6467 – 6476;,
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. 14667-47-1, name is Methyl 2-aminonicotinate. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H8N2O2

Solid phosgene (3.6 mmol) and 1,4-dioxane (20 mL) were added to the reaction flask and cooled to 0 C.Slowly add and stir6-Amino-2,2,7-trifluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (8 mmol)And 20 mL of a 1.4-dioxane composition solution.After the system was further stirred at this temperature for 30 min, it was heated to reflux for 10 h.The system was cooled to room temperature and dry nitrogen was introduced into the solution for 1 h. To the system was added 2-aminonicotinate methyl ester (8 mmol), and the system was further heated to reflux for 6 h.After the reaction is completed, the system is cooled to room temperature, a solid is precipitated, and suction filtration is performed.After washing with ether,Drying light brown solid 4.39g,Yield: 85%.

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, 14667-47-1, Methyl 2-aminonicotinate.

Reference:
Patent; Shandong Xian Da Agrochemical Co., Ltd.; Xi Zhen; Wang Xianquan; Wang Dawei; (28 pag.)CN108727367; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 573675-25-9, 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. 573675-25-9, name is 5-Bromo-3-nitropicolinonitrile. A new synthetic method of this compound is introduced below.

Under nitrogen atmosphere, a solution of 5-bromo-3-fluoro-pyridine-2-carbonitrile (1.005 g, 5.00 mmol) in dry N,N-dimethylformamide (15 ml) was cooled to -50C and to this was added dropwise a freshly prepared solution of sodium ethanethiolate (0.429 g, 5.10 mmol) in dry N,N-dimethylformamide (5 ml). After stirring at -50C for 30 minutes, the cooling bath was removed and the mixture was allowed to warm to room temperature. Water and brine were added and the aqueous mixture was extracted with ethyl acetate. After separation, the organic layer was washed twice with brine, dried over sodium sulfate and concentrated. The crude product was purified over silica by flash column chromatography (0 to 40% gradient of ethyl acetate in heptane) to afford the title compound (0.93 g) as a solid. GCMS (method 3): 242/244 (M)+, retention time 6.33 min. H-NMR (CDCI3, ppm) 1.41 (3H), 3.06 (2H), 7.82 (1 H), 8.49 (1 H). Alternative preparation method: Under nitrogen atmosphere, a solution of 5-bromo-3-nitro-pyridine-2- carbonitrile (45.35 g, 199 mmol) in dry N,N-dimethylformamide (500 ml) was cooled to -50C and to this was added dropwise a freshly prepared solution of sodium ethanethiolate (17.4 g, 207 mmol) in dry N,N-dimethylformamide (200 ml) (not a completely clear solution). After complete addition, stirring was continued at -50C for 30 minutes. Water and brine were added and the cooling bath was removed. The aqueous mixture was extracted with ethyl acetate. After separation, the water layer was extracted with ethyl acetate once more. The combined the organic layers were washed twice with brine, dried over sodium sulfate and concentrated. The crude product was purified over silica by flash column chromatography (0 to 25% gradient of ethyl acetate in heptane) to afford the title compound (33.9 g) as a solid. LCMS (method 1 ): 243/245 (M+H)+; retention time: 0.95 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,573675-25-9, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; EMERY, Daniel; BUCHHOLZ, Anke; (145 pag.)WO2017/16910; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem