Day: April 20, 2022

Reference of 57883-25-7 ,Some common heterocyclic compound, 57883-25-7, molecular formula is C7H8BrNO, 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.

To a solution of 3-bromo-2-ethoxy-pyridine (350 mg, 1.7 mmol) in NMP (2 mL) was added Zn(CN)2 (244 mg, 2.1 mmol) and Pd(dppf)C12 (127 mg, 0.17 mmol). The mixture was degassed with N2 and heated at 140C under microwave irradiation for 1 hour. The mixture was cooled to roomtemperature and filtered through celite. The filtered cake was washed with ethyl acetate (30 mL). The filtrate was washed with water (20 mL x 2) and brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (0%20% ethyl acetate in petroleum ether) to give 2-ethoxynicotinonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57883-25-7, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

Step-1: Preparation of 2-(2,6-Bis-benzyloxy-pyridin-3-yl)-2,6-dihydro-4H-pyrrolo[3,4- c]pyrazole-5-carboxylic acid tert-butyl ester (26-2) (1327) (1328) Compound 26-2 was synthesized according to Scheme 26. Yield: 12%; LC MS: ES+ 499.3.

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; CHEN, Chi-li; DUPLESSIS, Martin; HE, Minsheng; LAZARSKI, Kiel; (980 pag.)WO2017/197051; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56946-65-7, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine, 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, 56946-65-7, blongs to pyridine-derivatives compound. HPLC of Formula: C8H7Cl2N

To a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[Z?]pyridine (0.152 g, 0.81 mmol) in dioxane (3 mL) was added 2-(tributylstannyl)oxazole (0.318 g, 0.89 mmol) and tetrakis(triphenylphosphine)palladium (0.046 g, 0.040 mmol). The mixture was purged with nitrogen and then heated to 110 C under sealed conditions for 16 h. After this time, the mixture was diluted with water and extracted with ethyl acetate. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.061 g, 34%) as a white solid. MW = 220.66. ]H NMR (CDC13, 500 MHz) delta 7.94 (s, 1H), 7.78 (s, 1H), 7.29 (s, 1H), 3.19 (t, / = 7.5 Hz, 2H), 3.06 (t, / = 7.5 Hz, 2H), 2.22 (quin, J = 7.5 Hz, 2H); APCI MS m/z 221 [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,56946-65-7, its application will become more common.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 885588-17-0, Adding some certain compound to certain chemical reactions, such as: 885588-17-0, name is 5-Fluoro-2-methylisonicotinic acid,molecular formula is C7H6FNO2, 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 885588-17-0.

To a mixture of 5-fluoro-2-methylisonicotinic acid (200 mg) in dichloromethane (7 ml) und DMF (1 ml) was subsequently added at 22 C EDCI (198 mg), HOBT (158 mg) and triethylamine (163 mg) and stirring was continued for 15 min. l,3,3-Trimethyl-2-oxoindoline-6- carbohydrazide (165 mg) was added and stirring was continued for 18 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 10% MeOH in dichloromethane) to give the title compound (186 mg, 62%) as yellow oil. MS (ESI, m/z): 371.1 [(M+H)+].

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. 885588-17-0, 5-Fluoro-2-methylisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-88-5 ,Some common heterocyclic compound, 1221171-88-5, molecular formula is C6H5F3N2O, 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.

The product of Example 158B (62 mg, 0.11 mmol) and (1509) bis(tetramethylene)fluoroformamidinium hexafluorophosphate (50 mg, 0.16 mmol, Alfa) were charged to a sealed tube, and a solvent mixture of dichloromethane (0.26 mL) and N,N- diisopropylethylamine (0.083 mL, 0.47 mmol) was added in one portion. The resulting mixture was stirred at ambient temperature for 30 minutes and 5-(trifluoromethoxy)pyridin-2-amine (22.5 mg, 0.13 mmol, Astatech) was added. The tube was sealed and stirred at 75 C for 18 hours. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (3 mL), filtered through a glass microfiber frit and purified by preparative HPLC [YMC TriArt CI 8 Hybrid 5 mupiiota column, 50 x 100 mm, flow rate 70 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (12 mg, 0.023 mmol, 22% yield). JH NMR (400 MHz, DMSO-<) ppm 9.95 (s, 1H), 8.39 - 8.36 (m, 1H), 8.11 (dd, J = 9.2, 0.6 Hz, 1H), 7.83 (ddd, J = 9.2, 3.0, 1.0 Hz, 1H), 7.48 - 7.41 (m, 2H), 7.00 (dd, J = 11.4, 2.8 Hz, 1H), 6.78 (ddd, J = 9.0, 2.8, 1.2 Hz, 1H), 4.42 (s, 2H), 1.92 - 1.78 (m, 12H). MS (APCI+) m/z 516 (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,1221171-88-5, its application will become more common. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 886365-46-4, Adding some certain compound to certain chemical reactions, such as: 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid,molecular formula is C7H6ClNO2, 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 886365-46-4.

To a solution of tert-butyl ((3aR,4R,8S)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39BA, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-chloro-3-methylpicolinic acid (92.4 mg, 0.53 mmol) followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by preparative TLC (silica gel, dichloromethane / ethyl acetate 1: 1, UV) to yield, after drying in vacuo, the title compound as a yellow solid (100 mg, 50% yield). MS (ES+) m/z 579.2 [M+H].

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. 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3430-26-0, 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. 3430-26-0, name is 2,5-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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.

5-bromo-4-methyl-pyridine-2-carbonitrile:To a solution of 2,5-dibromo-4-methylpyridine (15 g, 59.8 mmol, Eq: 1.00) in DMF (100 ml) was added copper(1) cyanide (4.28 g, 47.8 mmol, Eq: 0.8) and sodium cyanide (2.34 g, 47.8 mmol, Eq: 0.8). The reaction mixture was refluxed for 20 hr at which point a precipitate formed. Upon cooling water was added and the mixture sonicated. The solids were filtered and washed with water. The resulting filtrate was extracted with EtOAc and the organic layers then combined, washed with water and brine, and concentrated under reduced pressure. The crude material was then purified by column chromatography (0-10% EtOAc/Hex gradient) to give 5-bromo-4-methyl-pyridine-2-carbonitrile (5 g, 42.4% yield) as a white solid.

According to the analysis of related databases, 3430-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90334; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 582303-10-4 ,Some common heterocyclic compound, 582303-10-4, molecular formula is C8H11NO, 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 this alcohol compound (32.2 g, 235 mmol) in 144 ml toluene and 120 ml CHCl3 was added dropwise to a solution of SOCl2 (18.8 ml, 259 mmol) in 24 ml toluene, all the while maintaining the internal temperature between 23 and 35. After the end of the addition the reaction mixture was vigorously stirred at 35 for 1.5 h and water pump vacuum was applied until the solvent was completely evaporated. The brown precipitate was resuspended in toluene, rapidly filtered off and washed three times with toluene. Drying in the desiccator (aspirator vacuum) gave 33.8 g (176 mmol, 75%) of 5-(chloromethyl)-2,6-dimethylpyridine hydrochloride as a light brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,582303-10-4, its application will become more common.

Reference:
Patent; Phan, Hieu Trung; Nguyen, Lan Mong; Azoulay, Raymond; Diep, Vinh Van; Eschenhof, Harald; Niesor, Eric Joseph; Bentzen, Craig Leigh; Ife, Robert John; US2005/124586; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 25194-01-8, 2,6-Dichloro-4-nitropyridine, 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, Product Details of 25194-01-8, blongs to pyridine-derivatives compound. Product Details of 25194-01-8

REFERENCE SYNTHESIS EXAMPLE 1 Synthesis of 2,6-dichloro-4-methoxypyridine used in the Synthesis example 6 To a tetrahydrofuran solution containing methanol (0.37 g, 0.0104*1.1 mol), sodium hydride (0.44 g, (ca.60% in mineral oil), 0.0104*1.05 mol) was added. Then 2,6-dichloro-4-nitropyridine (2.00 g, 0.0104 mol) was added thereto and the mixture was stirred for about 2 hours at room temperature. After it was confirmed that there was no bubbling with the addition of methanol (0.5 g), the mixture was stirred for about 1 hour. The reaction solution was partitioned between ethyl acetate and water. The obtained organic layer was washed successively with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, then dried over anhydrous sodium sulfate and concentrated to obtain the end product which was almost pure. Yield: 1.63 g (88%). Solid. Melting point: 94-96 C. 1 H-NMR (60 MHz, CDCl3, delta): 3.79(3H,s), 6.70(2H,s).

The synthetic route of 25194-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US5624942; (1997); A;,
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.52559-11-2, name is Pyridine-2,3,4-triamine, molecular formula is C5H8N4, molecular weight is 124.14, as common compound, the synthetic route is as follows.Safety of Pyridine-2,3,4-triamine

Dissolve 2,3, 4-triaminopyridine (2.5 mmol) in water (20 mL). Add NAHCO3 (0.63 g, 7.5 mmol), dioxane (10 ML), AND 2-BROMO-1-(3-TRIRLUOROMETHYL-PYRIDIN-2-YL)-ETHANONE hydrobromide (0.5 g) and stir at 100C for 2 hours. Cool the mixture and extract with EtOAc (4 X 10 mL). Wash the combined organic extracts with brine and dry over NA2S04. Purify the residue by preparative HPLC to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52559-11-2, Pyridine-2,3,4-triamine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/7652; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem