Day: April 7, 2022

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

Application of 1403899-44-4 ,Some common heterocyclic compound, 1403899-44-4, molecular formula is C9H11ClN2, 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.

Alternative procedure: Potassium teit-butoxide (600 mg, 5.36 mmol) was added to a stirred solution of 6-chloro-3,3-dimethyl-2,3-dihydro-1 H-pyrrolo[3,2-c]pyridine (800 mg, 4.38 mmol) in anhydrous THF (15 mL) and the mixture was stirred at room temperature for 10 minutes. Asolution of di-teit-butyl dicarbonate (1.07 g, 4.89 mmol) in anhydrous THF (15 mL) was added and the mixture was stirred at room temperature overnight. The organic solvent was removed in vacuo, the aqueous residues were diluted with water (100 mL) and extracted with EtOAc (2 x 200 mL). The organic layers were combined and the solvent was removed in vacuo to afford the title compound (1.19g, 96%), NMR data consistent with those previouslyobtained.

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. 1403899-44-4, 6-Chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; MILLEMAGGI, Alessia; HOWARD, Steven; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; WO2014/60768; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 189230-41-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 189230-41-9 as follows.

b) Preparation of intermediate 34A mixture of intermediate 33 (1.8 g, 9.57 mmol) and 4-fluoro-benzoic acid (1.34 g, 9.57 mmol) in polyphosphoric acid (25 g) was stirred and heated for 1 h at 180 0C. The r.m. was cooled to r.t, and water was added. The resulting sol. was neutralized with K2Ctheta3, and the resulting precipitate was filtered off and washed with water. Yield: 1 g of crude intermediate 34, which was used as such in the next reaction step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; BISCHOFF, Francois Paul; ZHUANG, Wei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; MACDONALD, Gregor, James; OEHLRICH, Daniel; WO2010/94647; (2010); A1;,
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. 1206775-52-1, name is 5-Bromo-6-methoxypicolinaldehyde, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-6-methoxypicolinaldehyde

(1) (5R) -5 – [(1,3- benzothiazol-2-ylsulfonyl) methyl] pyrrolidin-2-one (2.80 g), in tetrahydrofuran (170 mL) solution of lithium chloride (824 mg), argon gas atmosphere, at -78 , toluene solution (0.5M, 39mL) of potassium hexamethyldisilazide, and the mixture was stirred at the same temperature for 1 hour. Tetrahydrofuran (10 mL) solution was added to thereto 5-bromo-6-methoxy-pyridine-2-carbaldehyde (1.75g), and stirred at the same temperature for 30 minutes. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, after filtration, concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform: ethyl acetate = 50: 50) to give, (5R) -5 – [(Z) -2- (5- bromo-6-methoxy-pyridin-2-yl) ethenyl] pyrrolidin-2-one (900 mg) as a pale yellow oily substance.

The synthetic route of 1206775-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88912-24-7, 5,6-Dichloropicolinic 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, Safety of 5,6-Dichloropicolinic acid, blongs to pyridine-derivatives compound. Safety of 5,6-Dichloropicolinic acid

A four-neck 500 milliliter (mL) round bottomed flask was fitted with a thermocouple/J-KEM controller, mechanical stirrer, condenser that vented to a knock-out pot then to a 12% sodium hydroxide (NaOH) scrubber and a stopper. To the vessel was added concentrated sulfuric acid (H2SO4; 27.0 grams (g), 0.28 moles (mol)) and sulfolane (28.9 g). This mixture was warmed to 130 C. and then the solid trichloromethyl-pyridine (70.2 g, 0.26 mol) was added in portions over ca. 1 hour (h). Vigorous degassing to the caustic trap was observed. After the addition was complete, the mixture was stirred at 130 C. for 2 h and then allowed to cool to room temperature with stirring overnight resulting in a thick taffy. The mixture was warmed to 70 C., and a sample was taken for high performance liquid chromatography (HPLC) analysis which indicated a very clean conversion to the corresponding carboxylic acid. To the pot at 70 C. was carefully added isopropyl alcohol (IPA; 83.2 g, 1.39 mol) in portions over about 45 minutes (min) Initially there was vigorous degassing to the NaOH/caustic trap. After the addition was complete, the clear brown solution was stirred at 70 C. for 1 h. The 70 C. solution was added to crushed ice (361 g) with swirling of the flask. At the end of the addition, there was very little ice in the slurry. The slurry was cooled in the refrigerator for 1 h, and the solid was collected via filtration. The cake was washed with IPA/water (31 g/31 g) and then water (65 g). The material was allowed to air dry in a hood to a constant weight providing the product as a light beige solid (55 g, ca. 89%): HPLC purity was 98.5%; EIMS (70 eV) m/z 235, 233 (M+, 1%, 2%), 220, 218, 194, 192, 176, 174, 149, 147 (100%); 1H NMR (400 MHz, CDCl3) 7.98, 7.91 (ABq, J=8.0 Hz, 2H), 5.30 (m, 1H), 1.41 (d, J=4.0 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88912-24-7, 5,6-Dichloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Allen, Laura; Sanford, Melanie; Lee, Shin Hee; Bland, Douglas; Cheng, Yang; Roth, Gary; Muhuhi, Joseck M.; US2015/141654; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem