Pyridine-derivatives

Reference of 70593-57-6 , The common heterocyclic compound, 70593-57-6, name is 4,6-Dichloronicotinamide, molecular formula is C6H4Cl2N2O, 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 4,6-dichloronicotinamide (400 mg, 2.09 mmol), 3-iodobenzylamine (0.285 mL, 2.13 mmol) and DIEA (0.500 mL, 2.87 mmol) in NMP (5 mL) was stirred at 90 C for 48 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-100% EtOAc in hexane to give 6-chloro-4-(3-iodobenzylamino)nicotinamide as a solid (266 mg).

The synthetic route of 70593-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Portola Pharmaceuticals, Inc.; US2012/108566; (2012); 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

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

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

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

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

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

Electric Literature of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, 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.

Example 140 To a suspension of NaH (60% dispersion in mineral oil, 1.34 g, 0.056 mol) in THF (10 mL), a solution of 5-bromopyridin-2-ol (2.5 g, 0.014 mol) in THF (50 mL) was added and the resulting mixture was stirred at RT for 1 h. To this mixture, iodoethane (10.9 g, 0.07 mol) was added and the mixture was stirred at RT overnight. The mixture was quenched with water and washed with NH4Cl solution. The organic phase was separated, then concentrated in vacuo and the residue was purified by flash chromatography on silica gel (50-100% PE-AE) to afford 5-bromo-1-ethylpyridin-2(1H)-one.

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 13466-38-1, 5-Bromopyridin-2-ol.

Reference:
Patent; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6937-03-7, 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 6937-03-7 as follows.

To solution of (2,4,5-trichloro-phenoxy)-acetic acid (150 mg, 0.59 mmol), 2-amino isonicotinic acid methyl ester (179 mg, 1.18 mmol) and DMAP (144 mg, 1.18 mmol) in DMF 13 mL was added PyBOP (614 mg, 1.18 mmol) at room temperature. Reaction mixture was stared at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:1) to give 2-[2-(2,4,5-trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.056 g, 24.45% yield). 1H NMR (DMSO-d6, 300 MHz) 10.89 (1H, s, CONH), 8.54 (2H, d, J=5.4 Hz, pyridine), 7.85 (s, 1H, aromatic), 7.58 (1H, dd, J=1.35 &4.95 Hz, pyridine), 7.48 (1H, s, aromatic), 5.05 (2H, s, OCH2), 3.89 (3H, s, OCH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6937-03-7, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16110-09-1, 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 16110-09-1 as follows.

Step 1 Synthesis of Ethyl 5-chloropyridin-2-carboxylate: 1.2 g (8.2 mmol) of 2,5-dichloropyridine was dissolved in 50 ml of acetonitrile. 1.46 g (9.7 mmol) of sodium iodide and 0.7 ml (9.7 mmol) of acetyl chloride were added to the obtained solution, and they were stirred at 50 C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 15 ml of DMF. 182 mg (0.8 mmol) of palladium acetate, 147 mg (0.56 mmol) of triphenylphosphine, 2.3 ml of ethanol and 1.3 ml (9.7 mmol) of triethylamine were added to the obtained solution, and they were stirred in the presence of carbon monoxide at 70 C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound. Yield: 250 mg (1.35 mmol) (16%) H-NMR (CD3Cl) delta 1.44 (3H, t), 4.47 (2H, d), 7.82 (1H, dd), 8.09 (1H, d), 8.69 (1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16110-09-1, its application will become more common.

Reference:
Patent; AJINOMOTO CO. INC; US2003/186969; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem