Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid, 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, Recommanded Product: 2-(2-Chloropyridin-3-yl)acetic acid, blongs to pyridine-derivatives compound. Recommanded Product: 2-(2-Chloropyridin-3-yl)acetic acid

[0540] To a stirred solution of diisopropyl amine (0.82 mL, 5.8 mmol) in anhydrous THF (5 mL) cooled to -15C was added n-butyl lithium (2.5 M in hexanes, 2.3 mL, 5.8 mmol) slowly, maintaining the temperature of the flask between -10C and 0C. The resultant mixture was stirred at room temperature for 15 minutes before being cooling to 0C. The LDA thus formed was added to a rapidly stirred suspension of 2-(2-chloropyridin-3-yl)acetic acid (500 mg, 2.9 mmol) in anhydrous THF (10 mL) at 0C. The resultant bright yellow suspension was stirred at 0C for 15 min. A solution of 2-fluoro-4-iodo-l -isothiocyanatobenzene (814 mg, 2.9 mmol) in anhydrous THF (10 mL) was then added to the reaction mixture (brown suspension) and heated to 65C for 18 hours. The reaction mixture was cooled and the volatiles removed in vacuo. The resultant crude product was redissolved in THF, cooled to 0C and 10% aqueous acetic acid in water (10 mL) was added slowly. Acetonitrile (5 mL) was added slowly until a brown solid developed, the solid was isolated by filtration and washed with ether and acetonitrile to give the title compound. LC/MS: [M+l]+ 415; NMR (300 MHz, DMSO-d6): d 10.74 (s, 1H), 9.21 (s, 1H), 8.36-8.25 (m, 2H), 7.79 (d, J = 1.8 Hz, 1H), 7.68-7.61 (m, 1H), 7.51 (t, J=8.5 Hz, 1H), 7.42- 7.31 (m, 1H).

The synthetic route of 61494-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NFLECTION THERAPEUTICS, INC.; TSAI, Kenneth, Y.; KINCAID, John; SARIN, Kavita, Yang; (319 pag.)WO2020/106303; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55304-80-8, Adding some certain compound to certain chemical reactions, such as: 55304-80-8, name is 2,6-Dibromo-3-nitropyridine,molecular formula is C5H2Br2N2O2, 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 55304-80-8.

N, N-Dimethyl-N’- (6-bromo-3-nitropyridin-2-yl) sulfonic acid Stir a mixture of 2,6-dibromo-3-nitropyridine (11. 3g, 39.25 mmol) and N, N- dimethylsulfamide (0.006 g, 47.10 mmol) in DMF (40 mL). Add lithium hydride (0.81 g, 102.05 mmol) and stir at RT overnight. Add 100 mL of water and 3 N HC1 until pH = 7. Filter the yellow solid to provide the title compound (93%). 1H NMR (DMSO-d6) 8 10.25 (br s, 1H), 8.41 (d, J= 8.59 Hz, 1H), 7.50 (d, J= 8.59 Hz, 1H), 2.95 (2,6H).

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. 55304-80-8, 2,6-Dibromo-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/75478; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route 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.

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 1 h. 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 114a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO) delta 10.21 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.79 (d, J=5.0 Hz, 1H).

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. 22918-01-0, 2-Bromo-4-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65515-39-1, 2-Methoxy-4,6-dimethylnicotinonitrile, 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, 65515-39-1, blongs to pyridine-derivatives compound. SDS of cas: 65515-39-1

Add a I M solution of DIBAL-H in toluene (240 mL, 240 mmol) to a solution of 2-methoxy-4,6-dimethyl-pyridine-3-carbonitrile (48 g, 295.95 mmol) in DCM (480 mL)at 0 C over 2 hr. Remove the ice bath after 1 hr and stir at RT overnight. Cool in a waterbath at RT and quench by slowly adding a mixture of lMaqueous HC1 (192 mL) andAcOH (192 mL). Add DCM, separate the layers, wash the organic phase with saturated aqueous NaC1, dry over Na2504, filter and concentrate in vacuo. Subject the resulting residue to chromatography on silica, eluting with a gradient of 0-20% EtOAc/hexane to afford title compound as a solid (22.6 g, 46% yield) after solvent evaporation. ES/MS(mlz): 166 (M+H). ?H NMR (400.1 MHz, CDC13) oe 2,43 (s, 3H), 2.54 (s, 3H), 4.01 (s,3H), 6.61 (s, 1H), 10.48 (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,65515-39-1, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; DOMINGUEZ, Esteban; GUO, Deqi; MADER, Mary Margaret; NGUYEN, Anh-Quan Hannah; DEL PRADO, Miriam Filadelfa; RICHETT, Michael Enrico; RODRIGUEZ, Michael John; YIP, Yvonne Yee Mai; YU, Kuo-Long; (165 pag.)WO2017/35060; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 38923-08-9, 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. 38923-08-9, name is Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

A solution of 250mg (1.01 mmol) of ethyl 6-ni-troimidazo[ 1 ,2-a]pyridine-2-carboxylate in 20 ml of ethanolwas hydrogenated in the presence of 30 mg of palladium(10% on activated carbon) at RT and standard pressure for5 h. The reaction mixture was then filtered through Celiteand the residue was washed with ethanol. The combinedfiltrates were concentrated under reduced pressure and dried.Yield: 215 mg (quant.)10502] LC/MS [Method 5]: R=1.40 mm; MS (ESIpos):mlz=206 (M+H),10503] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=8.33 (s,1H), 7.66 (s, 1H), 7.37 (d, 1H), 6.94 (dd, 1H), 5.11 (s, 2H),4.26 (q, 2H), 1.29 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38923-08-9, Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHRIG, Susanne; HILLISCH, Alexander; STRASSBURGER, Julia; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; BUCHMUeLLER, Anja; GERDES, Christoph; SCHAeFER, Martina; TELLER, Henrik; JIMENEZ NUNEZ, Eloisa; SCHIROK, Hartmut; KLAR, Juergen; (66 pag.)US2016/272637; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 866775-18-0, 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 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate. This compound has unique chemical properties. The synthetic route is as follows.

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 ml); Sodium hydroxide (2.0 M aqueous solution) (14.04 ml, 28.1 mmol) was added and the suspension was stirred at RT overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in water (100 ml) and then acidifed by the addition of 5.0M HCI(aq). The product was extracted into ethyl acetate (2 x 75 ml) and the combined organic extracts were washed with water (50 ml), brine (25 ml), dried (MgS04) and concentrated under reduced pressure to afford the title product as a yellow solid. H-NMR: 9400MHz, DMSO-d6) ? 13.24 (1 H, br s, C02H), 7.74 (1 H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1 , 287.1 [M+H]+

According to the analysis of related databases, 866775-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren, Mark; WO2013/38381; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 915720-71-7, 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. 915720-71-7, name is (S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate. A new synthetic method of this compound is introduced below.

In a 5 mL microwave vial a solution of (S)-tert-butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate (60 mg, 0.2 mmol), (4-fluoro-3-methylphenyl)boronic acid (37 mg, 0.24 mmol), Sodium bicarbonate (0.2 mL, 0.4 mmol, 2 M aqueous solution) in Dioxane (2 mL) was bubbled N2 for 3mm then CI2Pd(dppf)CH2CI2 (16 mg, 0.02 mmol) was added. The capped tube was heated to10000 for 16 h. After cooling the reaction mixture was diluted with EtOAc (10 mL) and washed with water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3 x 10 mL). Combined organics were dried over Na2504, filtered and concentrated. The crude material was purified through silica gel column chromatography (EtOAc in Heptane 12 to 100%) to givea white solid (66 mg, 80% yield). LCMS tR = 1.43 mm; MS mlz 331.1 (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,915720-71-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; CAFERRO, Thomas Raymond; CHEN, Zhuoliang; CHO, Young Shin; COSTALES, Abran Q.; LEVELL, Julian Roy; LIU, Gang; MANNING, James R.; SENDZIK, Martin; SHAFER, Cynthia; SHULTZ, Michael David; SUTTON, James; WANG, Yaping; ZHAO, Qian; WO2014/141104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113293-70-2, 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. 113293-70-2, name is 2,6-Dichloroisonicotinaldehyde. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloroisonicotinaldehyde (30 g, 170 mmol) in dichloromethane (450 mL) was added diethylaminosulfur trifluoride (90 mL, 682 mmol) in dichloromethane (200 mL) at -78 C. over 10 minutes. The reaction mixture was warmed to 25 C. and stirred for 2 hours. The reaction mixture was quenched with ice water (500 mL) and extracted with dichloromethane (3 × 300 mL). The combined organic layers were washed with NaHCO 3 (saturated aqueous solution, 200 mL), water (200 mL) and brine (200 mL), dried over Na 2 SO 4, filtered and concentrated to give the desired product (20 g, 57% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 ml_) and the resulting mixture stirred at rt for 8h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 ml_). The resultingcolourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield).1H-NMR (400 MHz, DMSO-d6,298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid, molecular formula is C8H8N2O2, 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. Formula: C8H8N2O2

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3- (6-AMINO-PYRIDIN-3- yl) acrylic acid (164 mg, 1.0 mmol), methyl- (3-methyl-benzofuran-2-ylmethyl) amine (193 mg, 1.1 mmol), HOBTNo.H2O (149 mg, 1.1 mmol) and DIPEA (525 PL, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The oraganic layer was washed with brine (2 x 30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2Cl2) of the residue furnished pure free base which was dissolved in CH2C12 (10 mL). After addition OF HCL (1.5 mL, 1M in ether), the solvents were evaporated, washed with ether and dried to afford the title compound (195 mg, 54%). 1H NMR (300 MHz, DMSO-d6) 8 8.36 (m, 3H), 7.50 (m, 3H), 7.25 (m, 3H), 7.02 (m, 1H), 4.98 and 4.79 (rotamers, 2s, 2H), 3.17 and 2.92 (rotamers, 2s, 3H), 2.26 (s, 3H). MS (ESI) nile 322 (M+H) +.

With the rapid development of chemical substances, we look forward to future research findings about 167837-43-6.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem