Category: pyridine-derivatives

Related Products of 1122-71-0, 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.1122-71-0, name is 6-Methyl-2-pyridinemethanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.

A solution of 0.45 g (3.65 mmol, 1.0 eq.) of of (6-methylpyridin-2-yl)methanol in 8 mL of anhydrous acetonitrile was added to a rapidly stirred mixture of 0.89 g mmol (5.48 mmol, 1.5 eq.) of 1,1?-carbonyldiimidazole in 1.5 mL of anhydrous acetonitrile. The reaction mixture was stirred for 40 minutes, and the volatiles were then removed in vacuo. The residue was redissolved in 30 mL of ethyl acetate and washed with 30 mL of water. The layers wereseparated and the organic phase was washed with 2 x 20 mL of sat. sodium bicarbonate solution, followed by 20 mL of brine. The organic phase was dried (Na2SO4), filtered and evaporated to dryness. The residue was dried under high vacuum to provide 0.65 g (3.0 mmol, 82%) of (6-methylpyridin-2-yl)methyl imidazole-1-carboxylate (0.65g, 82% yield). ?H NMR (300 MHz, CDC13) oe: 8.20 (t, 1H), 7.65 (t, 1H), 7.50-7.45 (m, 1H), 7.23 (d, 1H), 7.17(d, 1H), 7.09 (m, 1H), 5.49 (s, 2H), 2.59 (s, 3H).

Statistics shows that 1122-71-0 is playing an increasingly important role. we look forward to future research findings about 6-Methyl-2-pyridinemethanol.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; COLE, Andrew G.; KULTGEN, Steven; (203 pag.)WO2018/52967; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 874959-68-9 , The common heterocyclic compound, 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride, molecular formula is C5H3BrClNO2S, 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 58(a) l-(5-Bromo-pyridine-2-sulfonyl)-4-methyl-piperazine; 5-Bromopyridine-2-sulfonyl chloride (as described in Example 52(b) (55.0 mg, 0.214 mmol) was dissolved in CH2Cl2 (1 mL) and 1-methyl-piperazine (26 muL, 0.236 mmol) was added. Stirring was continued at room temperature for 3 hours and saturated aqueous NaHCO3 (1 mL) was added. The mixture was diluted with CH2Cl2 (5 mL) and the aqueous phase was extracted with CH2Cl2 (3 x 5 mL). The combined organic phases were dried (Na2SO4) and concentrated to afford the title compound (61 mg, 89%). 1H NMR (400 MHz, CDCl3) delta ppm 2.29 (s, 3 H) 2.33 – 2.38 (m, 2 H) 2.45 – 2.50 (m, 2 H) 3.10 – 3.18 (m, 2 H) 3.30 – 3.37 (m, 2 H) 7.31 (d, J=4.29 Hz, 1 H) 7.81 (d, J=7.58 Hz, 1 H) 8.04 (dd, J=8.34, 2.27 Hz, 1 H); MS (ESI) m/z 321 (M + 1).

The synthetic route of 874959-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/2244; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65156-94-7, Adding some certain compound to certain chemical reactions, such as: 65156-94-7, name is 5-Chloro-1H-pyrrolo[3,2-b]pyridine,molecular formula is C7H5ClN2, 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 65156-94-7.

A mixture of 5-chloro-lH-pyrrolo[3,2-b]pyridine (1 g, 6.55 mmol, 1 equiv), 1,1,1- trifluoro-2-iodoethane (1.4 g, 6.55 mmol, 1 equiv) and CS2CO3 (2.1 g, 6.55 mmol, 1 equiv) in 10 mL of DMF was stirred for 4 hours at 60 C. The reaction was then quenched by the addition of 30 mL of water, extracted with 10 mL of ethyl acetate and the combined organic layers concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petr oleum ether (1/10) to afford the desired final product as a colorless oil in 42% yield.

According to the analysis of related databases, 65156-94-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); 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. 101079-63-4, name is 2,6-Dichloropyridine-3,4-diamine. A new synthetic method of this compound is introduced below., name: 2,6-Dichloropyridine-3,4-diamine

To a solution of intermediate 13 (16.00 g, 89.88 mmol) in EtOH (60 mL) was added triethyl orthoacetate (50 mL) and conc. HCl (4 mL) and the mixture was stirred at 100 C for 16 hours. The mixture was concentrated and diluted with water and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by column chromatography over silica gel (mobile phase gradient: from 100% petrol, 0% EtOAc to 0% petrol, 100% EtOAc). The product containing fractions were collected and the solvent was evaporated to give 11 g of intermediate 14 (57% yield, 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, 101079-63-4, 2,6-Dichloropyridine-3,4-diamine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; PILATTE, Isabelle, Noelle, Constance; QUEROLLE, Olivier, Alexis, Georges; ANGIBAUD, Patrick, Rene; BERTHELOT, Didier, Jean-Claude; COUPA, Sophie; DEMESTRE, Christophe, Gabriel, Marcel; MEERPOEL, Lieven; MERCEY, Guillaume, Jean, Maurice; MEVELLEC, Laurence, Anne; MEYER, Christophe; PASQUIER, Elisabeth, Therese, Jeanne; PONCELET, Virginie, Sophie; (104 pag.)WO2017/216293; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 80194-68-9, 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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid. A new synthetic method of this compound is introduced below.

A mixture of 2-amino-4-(trifluoromethylsulfanyl)phenol 1.0 g, 3-chloro-5-trifluoromethylpicolinic acid 1.08 g, EDC hydrochloride 1.10 g, and chloroform 10 mL was stirred at RT for 1 hr. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 3-chloro-5-trifluoromethyl-N-[2-hydroxy-5-(trifluoromethylsulfanyl)phenyl]picolinamide 1.94 g. 3-chloro-5-trifluoromethyl-N-[2-hydroxy-5-(trifluoromethylsulfanyl)phenyl]picolinamide 1H-NMR(CDCl3)delta: 8.78(1H, d), 8.15(1H, d), 8.09(1H, d), 7.37(1H, dd), 7.04(1H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Chemical Company, Limited; SHIMIZU, Chie; KAMEZAKI, Masashi; NOKURA, Yoshihiko; EP2952098; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 69950-65-8, 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 69950-65-8 as follows.

To methyl 5-formylpicolinate (1.0 g, 6.055 nimol) dissolved in ethanol-water (14.4 mL, 2: 1 ) was added hydroxylamine hydrochloride (0.463 g, 6.66 mmol) and sodium acetate (0.546 mg, 0.6661 mmol). The reaction mixture was stirred overnight at 55 C. The reaction was concentrated under reduced pressure and redissolved in EtOAc (100 mL). The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The solid residue was dissolved triturated with EtOAc, filtered and dried under reduced pressure affording methyl 6-(hydroxyimino)methyl)picoiinate (990 mg, 5.495 mmol, 91 %) as a beige solid. LCMS [M+H]+: 181.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69950-65-8, its application will become more common.

Reference:
Patent; ARQULE, INC.; BATES, Craig; EATHIRAJ, Sudharshan; INAGAKI, Hiroaki; LAPIERRE, Jean-Marc; MOMOSE, Takayuki; NAKAYAMA, Kiyoshi; ODAGIRI, Takashi; OTA, Masahiro; OTA, Yusuke; SHIBATA, Yoshihiro; TANDON, Manish; TSUNEMI, Tomoyuki; (371 pag.)WO2018/39310; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 136818-50-3, 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. 136818-50-3, name is 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Example 13Synthesis of3- ( (dimethylamino) methyl) -lH-pyrrolo [2, 3-£>]pyridine-2- carboxylic acid19Treatment of 2 with a mixture of dimethylamine and aqueous formaldehyde gives3- ( (dimethylamino) methyl) -lH-pyrrolo [2 , 3-£>]pyridine-2-carboxyl ic acid (19) by Mannich reaction.

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 136818-50-3, 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid.

Reference:
Patent; IRONWOOD PHARMACEUTICALS INCORPORATED; LUDRIGAN, Regina; JEFFREY, John; MERMERIAN, Ara; WO2010/5528; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6313-54-8, 2-Chloroisonicotinic 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, HPLC of Formula: C6H4ClNO2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H4ClNO2

Reference Production Example 14 To a mixture of 0.71 g of 2-amino-4-(trifluoromethyl)phenol, 0.63 g of 2-chloroisonicotinic acid and 7 ml of pyridine, 1.05 g of WSC was added and stirred while heating at 60C for four hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.77 g of 2-chloro-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide. [Show Image] 1H-NMR (DMSO-d6) delta: 10.12 (br s, 1H), 8.62 (d, J=5.1 Hz, 1H), 8.03-7.97 (m, 2H), 7.87 (dd, J=5.2, 1.3 Hz, 1H), 7.46-7.43 (m, 1H), 7.10 (d, J=8.2 Hz, 1H)

The synthetic route of 6313-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2274983; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1427-06-1, Methyl 6-fluoropyridine-3-carboxylate, 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: Methyl 6-fluoropyridine-3-carboxylate, blongs to pyridine-derivatives compound. Recommanded Product: Methyl 6-fluoropyridine-3-carboxylate

To a tetrahydrofuran (5 mL) solution of 2-((tert-butyldimethylsilyl)oxy)ethanol (Ark Pharm, 200 mg, 1.134 mmol) stirred at ambient temperature was added sodium hydride (60% dispersion in mineral oil, 68 mg, 1.701 mmol) in one portion. After 5 minutes, methyl 6- fluoronicotinate (Combi-Blocks, 176 mg, 1.134 mmol) was added. After the reaction was stirred for 5 minutes, N,N-dimethylformamide (1 mL) was added. After 30 minutes, the reaction mixture was concentrated under reduced pressure and taken up in a solvent mixture of N,N-dimethylformamide (1.5 mL) and methanol (1.5 mL). The resulting suspension was filtered through a glass microfiber frit, and the filtrate was purified by preparative HPLC [YMC TriArt C18 Hybrid 20 mum column, 25 × 150 mm, flow rate 80 mL/minute, 20-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (0.11 g, 0.35 mmol, 31% yield). MS (ESI+) m/z 312 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1427-06-1, Methyl 6-fluoropyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 109-04-6 ,Some common heterocyclic compound, 109-04-6, molecular formula is C5H4BrN, 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.

Step F: Preparation of 3-(2-pyridinyl)benzenamine; To a solution of 2-bromopyridine (1.6 g, 10 mmol) in dimethoxyethane (50 mL) and water (17 mL) was added 3-aminophenylboronic acid hemisulfate (1.86 g, 10 mmol), sodium carbonate (5.6 g, 52.8 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.3 g). The mixture was heated to reflux for 5 hours and then allowed to cooled to room temperature. Brine (50 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The organic extracts were dried (MgS04) and concentrated to leave the crude product. The crude product was purified by flash column chromatography to provide the title compound as a thick yellow oil (1.1 g). 11-1 NMR (CDC13) 8 8.6 (m, 1H), 7.69 (m, 2H), 7. 3 (m, 4H), 6.8 (m, 1H), 3.8 (br s 2H).

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. 109-04-6, 2-Bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E.I. DUPONT DE NEMOURS AND COMPANY; WO2005/40152; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem