Month: April 2022

Electric Literature of 76041-79-7, 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.76041-79-7, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-ol, molecular formula is C6H3BrF3NO, molecular weight is 241.99, as common compound, the synthetic route is as follows.

Methyl iodide (0.12 mL, 1.88 mmol) and Cs2C03(0.942 g, 2.89 mmol) were added to a solution of 5-bromo-3-(trifluoromethyl)-1 H-pyridin-2-one (0.350 g, 1.45 mmol) in DMF (3 mL) and the resulting mixture was stirred for 18 h at rt. The solvent was evaporated under reduced pressure, water (10 ml) was added to the residue and the aqueous phase was extracted with EtOAc (2 x 30 mL). The combined organic phases were washed with brine and dried over MgS04, filtered and concentrated under reduced pressure. The material was triturated with ether then dried to afford title compound, which was used in the next step without any further purification (0.32 g, 86%).1H NMR (500 MHz, CDCI3) delta 7.78 (d, J = 2.1 Hz, 1 H), 7.64 (d, J = 2.7 Hz, 1 H), 3.59 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 76041-79-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEOMED INSTITUTE; POURASHRAF, Mehrnaz; JACQUEMOT, Guillaume; CLARIDGE, Stephen; BAYRAKDARIAN, Malken; JOHNSTONE, Shawn; ALBERT, Jeffrey S.; GRIFFIN, Andrew; (180 pag.)WO2017/24412; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1186637-43-3 ,Some common heterocyclic compound, 1186637-43-3, molecular formula is C7H5BrN2O, 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 2-(tert-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-methoxypicolinonitrile (from step 1) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol %) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 100 C. and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-50% ethyl acetate in hexane to give 3-methoxybenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (acetone d-6): delta 8.91 (d, 1H), 8.34 (d, 1H), 7.63 (d, 1H), 7.51-7.53 (dd, 1H), 7.27-7.33 (m, 2H), 6.65 (br, 2H), 4.11 (s, 3H). LRMS [M+H]=226.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1186637-43-3, its application will become more common.

Reference:
Patent; GlaxoSmithKline Biologicals SA; Skibinski, David; Jain, Siddhartha; Singh, Manmohan; O’Hagan, Derek; (124 pag.)US9408907; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 669066-89-1, 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. 669066-89-1, name is 3-Amino-5-bromopicolinamide. A new synthetic method of this compound is introduced below.

(b) 3-Amino-5-bromopicolinic acid. A mixture of 3-amino-5- bromopicolinamide (28.2 g, 0.13 mol) and concentrated HCl (361 inL) was heated at reflux for 12 hours. The reaction mixture was allowed to reach room temperature, and the solid which precipitated was filtered. The filter cake was dissolved in water, and the pH of the aqueous solution was adjusted to pH = 4 with saturated NaOAc, and extracted with EtOAc (3 x). The combined organic extracts were dried over anhydrous MgSO4, and filtered. The filtrate was evaporated under reduced pressure, and the residue dried in vacuo to afford the title compound as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,669066-89-1, 3-Amino-5-bromopicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2008/76425; (2008); 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 885168-04-7, name is 5-Bromo-3-chloropicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 885168-04-7

2) In tetrahydrofuran (27 mL) was dissolved 5-bromo-3-chloro-N-methoxy-N-methyl- pyridine-2-carboxamide (2.66 g), the mixture was cooled under nitrogen atmosphere at -70C or lower, and a tetrahydrofuran (5 mL) suspension of lithium aluminum hydride (180 mg) was added dropwise to the mixture. The mixture was stirred at -70C or lower for 2 hours, then, water (10 mL) and a saturated brine (10 mL) were added dropwise to the mixture. A temperature of the mixture was raised to room temperature, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and a saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=100:0 to 90: 10) to obtain a mixture of an aldehyde compound and an aldehyde equivalent (2.1 g). To water (36 mL) were added 3,3-dibromo-l,l,l-trifluoropropan-2-one (6.61 g) and sodium acetate (4.02 g) and the mixture was stirred at 95C for 30 minutes. An aqueous solution obtained by ice-cooling the mixture was added to a mixture comprising the previously obtained mixture of the aldehyde/ aldehyde equivalent (1.8 g), 28% aqueous ammonia (18 mL) and methanol (36 mL) at room temperature, and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated, the residue was extracted with ethyl acetate, and the organic layer was washed with a saturated brine, and then, dried over anhydrous magnesium sulfate. After concentrating the mixture under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=80:20), and the obtained solid was collected by filtration, washed with isopropyl ether and dried to obtain 5-bromo-3-chloro-2-[5- (trifluoromethyl)-lH-imidazol-2-yl]pyridine (935 mg).MS (m/z): 326/328/330 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 885168-04-7.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SAKURAI, Osamu; SARUTA, Kunio; HAYASHI, Norimitsu; GOI, Takashi; MOROKUMA, Kenji; TSUJISHIMA, Hidekazu; SAWAMOTO, Hiroaki; SHITAMA, Hiroaki; IMASHIRO, Ritsuo; WO2012/81736; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185041-05-8, 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.185041-05-8, name is Methyl 2-chloro-4-iodonicotinate, molecular formula is C7H5ClINO2, molecular weight is 297.48, as common compound, the synthetic route is as follows.

2.0 g 2-chloro-4-iodo-nicotinic acid methyl ester (6.7 mmol), (6.7 mmol) and methyl pyrrolidone (NMP) in a mixture of 0.60 g of cuprous cyanide were heated to 10 ml containing N- 130 five hours, after cooling was diluted with 50 ml of ethyl acetate, the mixture was filtered and concentrated under reduced pressure, the residual material was dissolved in 25 ml of ethyl acetate after washing twice with 10 mL of aqueous ammonia, dried over magnesium sulfate and concentrated, the residual material was purified by silica gel column chromatography (moving phase: ethyl acetate: petroleum ether = 3% to 5%), to give the desired product, 2-chloro-nicotinic acid methyl ester cyano, a white solid (1.0 g, 5.1 mmol, 56% yield).

Statistics shows that 185041-05-8 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-4-iodonicotinate.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; ARNDT, JOSEPH; CHAN, TIMOTHY; GUCKIAN, KEVIN; KUMARAVEL, GNANASAMBANDAM; LEE, WEN-CHERNG; LIN, EDWARD YIN-SHIANG; SCOTT, DANIEL; SUN, LIHONG; THOMAS, JERMAINE; VAN VLOTEN, KURT; WANG, DEPING; ZHANG, LEI; ERLANSON, DANIEL; (469 pag.)TWI525093; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1138444-17-3, 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 1138444-17-3, name is 6-Bromo-2-chloro-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 6-bromo-2-chloro-3-iodopyridine (8.0 g, 25.1 mmol), (E)-2-(2- ethoxyvinyl)-4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolane (4.98 g, 25.1 mmol), cesium carbonate (16.38 g, 50.3 mmol), and [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (2.052,2.51 mmol) was added 1,4-dioxane (100 mL) and H20 (10 mL). A steady stream of N2 was bubbled through the reaction mixture for 15 minutes then the mixture was heated to 73 C for 20h. The mixture was cooled to ambient temperature, diluted with EtOAc, and washed successively with H20 (2X) and brine (lx). The organic layer was dried over MgSO4, filtered,and concentrated in vacuo. The residue was purified by silica gel column chromatography using a step gradient of 0-10-60% EtOAc/Hexanes as eluent. MS (M+H): 261.

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 1138444-17-3, 6-Bromo-2-chloro-3-iodopyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda, L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/123793; (2014); A1;,
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. 896139-85-8, name is Imidazo[1,2-a]pyridin-7-ol. A new synthetic method of this compound is introduced below., Recommanded Product: Imidazo[1,2-a]pyridin-7-ol

To a solution of intermediate 1 (500 mg, 1 .54 mmol, 1 .0 eq) and Imidazo[l,2-a]pyridin- 7-ol (248.6 mg, 1.85 mmol, 1.2 eq) in THF (20 mL) was added tributylphosphane (624.9 mg, 3.1 mmol, 2.0 eq) and (NE)-N-(piperidine-l-carbonylimino)piperidine-l- carboxamide (779 mg, 3.1 mmol, 2.0 eq) . The mixture was stirred at 15 C for 15 hrs. The solvent was removed. The residue was purified by flash column on silica gel (ISCO; 12 g SepaFlash Silica Flash Column, Eluent from 0% to 3% MeOH / DCM gradient 30 mL/min) and intermediate 78 (240 mg, 33.7% yield) was obtained as a light yellow solid.

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, 896139-85-8, Imidazo[1,2-a]pyridin-7-ol.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston Stanislas Marcella; LAWSON, Edward Charles; MEERPOEL, Lieven; PANDE, Vineet; PARADE, Marcus Cornelis Bernardus Catharina; SCHEPENS, Wim Bert Griet; SUN, Weimei; THURING, Johannes Wilhelmus John F.; VIELLEVOYE, Marcel; (186 pag.)WO2018/65365; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22918-01-0, Adding some certain compound to certain chemical reactions, such as: 22918-01-0, name is 2-Bromo-4-chloropyridine,molecular formula is C5H3BrClN, 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 22918-01-0.

Example 103a 2-Bromo-4-chloronicotinaldehyde 103a To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70 C. was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C. for another 1h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 103a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO-d6) delta 10.21 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.79 (d, J=5.0 Hz, 1H).

According to the analysis of related databases, 22918-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1122-43-6, 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. 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine. A new synthetic method of this compound is introduced below.

Compound 34C (50 mg, 0.14 mmol), potassium carbonate (39 mg, 0.28 mmol), and2,6-dimethylpyridin-3-ol (51 mg, 0.42 mmol) were stirred in DMF (2.5 mL). The reaction was purged with nitrogen, sealed in a vial, and then heated in a microwave reactor at 190C for eight minutes on high absorbance. The crude reaction mixture was concentrated in vacuo, redissolved in DCM, and washed with water. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude reaction mixture was purified using a silica gel cartridge with DCM/methanol (95/5) to provide compound 103 as an off white solid (60 mg, 96%). LCMS: 445.2 (MH’).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2009/55331; (2009); A2;,
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.62150-46-3, name is 4-Bromopicolinamide, molecular formula is C6H5BrN2O, molecular weight is 201.0207, as common compound, the synthetic route is as follows.category: pyridine-derivatives

third step:Add water to the 50 liter reactor, sodium hydroxide, stir to reduce the temperature to 0 , add bromine, drop the temperature to minus 10 degrees.Add the amide in batches and stir for one hour.Then heat to 80 degrees for one hour.The TCL was detected until the end of the reaction, and the temperature was lowered to room temperature and centrifuged to obtain a crude product which was crystallized from toluene to give a pure product of 1.5 kg.The ratio of each raw material in the third step of Example 1 and the reaction conditions of the third step and the purity and yield of the obtained product are shown in Table 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62150-46-3, 4-Bromopicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; Chengdu Tong Chuangyuan Pharmaceutical Technology Co., Ltd.; Shou Yuehan; (12 pag.)CN105153023; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem