Category: pyridine-derivatives

Electric Literature of 52605-96-6, 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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.

The boronic acid was prepared as described in Intermediate 4 to give 2.8mmole. (quant. crude). The boronic acid (2. 14MMOL) was dissolved in acetonitrile (2. 4ML) and 3-methoxy-2-chloropyridine (368mg; 2. 6mmol) was added. After mixing, tetrakis palladium was added (25mg; 0. OLMOL%), follwed by 0. 8ml of water and K2CO3 (887mg; 6. 5MOL). The reaction mixture was heated at 160C in A Personal Chemistry EMRYS Microwave for 300S. After reaction completion, the solvents were evaporated and the residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over MGSO4, filtered and evaporated. The residue was then dissolved in A 1 : 1 mixture of THF/42NKOH and heated until saponification was complete. The basic layer was then extracted with EtOAc and acidified with cone. HCI. The aqueous layer was then extracted three times with EtOAc. The combined organic layers were dried over MGS04, filtered and evaporated to give the desired material as A yellow solid (425MG ; 76%). MS :MH+= 264

Statistics shows that 52605-96-6 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-3-methoxypyridine.

Reference:
Patent; RENOVIS, INC.; WO2005/32493; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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 62002-31-7 as follows.

To a stirred solution of 4,5-dibromo-2-(oxan-2-yl)-2,3-dihydropyridazin-3-one (3 g, 8.88 mmol, 1 equiv.) and 1H,4H,5H,6H,7H-imidazo [4,5-c]pyridine (1.1 g, 8.88 mmol, 1.00 equiv.) in 1,4- dioxane (30 mL) was added DIEA (2.3 g, 17.75 mmol, 2 equiv.) dropwise at 0 degree Celsius under nitrogen atmosphere. The mixture was stirred at 100 degrees Celsius overnight. Desired product could be detected by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with CH2Cl2 / MeOH (10:1 to 5:1) to afford 4-bromo-5-[1H,4H,5H,6H,7H-imidazo[4,5-c]pyridin-5-yl]-2- (oxan-2-yl)-2,3-dihydropyridazin-3-one (3g, 88.89%) as white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 945954-94-9, name is Methyl 6-bromo-3-methoxypicolinate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 945954-94-9

A solution of methyl 6-bromo-3-methoxypicolinate (3.0 g, 12.19 mmol) andLiOHH2O (1.4 g, 33.36 mmol) in 1,4-dioxane / H20 (15 mL / 15 mL) was stirred at RT overnight. The mixture was filtered and the filtrate was adjusted to pH = 3 by aqueous HC1 (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2504 andconcentrated to give the crude product of 6-bromo-3-methoxypicolinic acid (2.1 g, yield: 73 %)without further purification. ?H-NMR (CDC13, 400 MHz) 10.05 (br s, 1H), 7.70 (d, J = 8.8 Hz,1H), 7.40 (d, J = 8.8 Hz, 1H), 4.01 (s, 3H). MS (M+H): 232 / 234.

With the rapid development of chemical substances, we look forward to future research findings about 945954-94-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 934180-48-0, 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.934180-48-0, name is 4-Chloro-2-methoxy-3-nitropyridine, molecular formula is C6H5ClN2O3, molecular weight is 188.57, as common compound, the synthetic route is as follows.

Tin(ll)chloride dihydrate (12 g, 53.19 mmol) was added to a solution of 4-chloro-2- methoxy-3-nitropyridine (2 g, 10.64 mmol) in ethyl acetate (30 ml.) and the resultant suspension heated at 70 C with stirring for 2 h. The reaction mixture was cooled to ambient temperature, the pH adjusted to pH 9-10 by addition of saturated sodium carbonate (aq.) and extracted with ethyl acetate (3 x 10OmL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by chromatography on silica gel with EtOAc:heptane (1 :9, v/v) as eluent afforded the product as a colourless oil (1.28 g, 76 %).Data for 3-amino-4-chloro-2-methoxypyridine: MS (ESI) m/z: 159/161 ([M+H]+).

The chemical industry reduces the impact on the environment during synthesis 934180-48-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; N.V. ORGANON; WO2007/39563; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19235-89-3, 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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. A new synthetic method of this compound is introduced below.

A three-neck, 3L round bottomed flask fitted with a mechanical stirrer and a reflux condersor was charged with 4-aminophenol (41.35 g, 0.38 mol) and N5N- dimethylacetamide (500 mL). The resulting solution was degassed with bubbling nitrogen before potassium tert-butoxide was added portionwise (44.54 g, 0.40 mol). The solution became green at first, then became an off-white suspension, to which was added 4- chloropyridine-2-carbonitrile (50.00 g, 0.36 mol) in N,N-dimethylacetamide (300 mL) in one portion. The mixture turned brown within minutes and it was heated to 900C overnight. In the next morning, the mixture was cooled to rt and the solvent was removed under vacuum. The resulting residue was partitioned between water (1.5 L) and EtOAc (1.5 L). K2CO3 was added to adjust the pH to slightly basic and the layers were separated. The aqueous layer was extracted with EtOAc (IL). The combined organic phase was dried over MgSO4, filtered and concentrated. The resulting residue was dissolved in dichloromethane and absorbed onto a plug of silica gel (~ 1 kg). It was then eluted with 25% to 75% EtOAc in hexanes to afford 4-(4-aminophenoxy)pyridine-2-carbonitrile (18.9 g, 25%): 1H NMR (DMSO-^5) delta ppm 8.48 (d, IH), 7.51 (d, IH), 7.04 (dd, IH), 6.83 (dd, 2H), 6.60 (dd, 2H), 5.18 (s, 2H); MS ES 212 (M+H), RT 0.97 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19235-89-3, 4-Chloropyridine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/110763; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58236-70-7, 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. 58236-70-7, name is 5-Bromo-3-chloropyridin-2(1H)-one, molecular formula is C5H3BrClNO, 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.

36.0 g (172.7 mmol) of 5-bromo-3-chloro-2-hydroxypyridine are stirred at 160° C. for 6 hours in 320 ml of phosphorus tribromide. The reaction mixture is cooled to room temperature and poured carefully into ice water. After 2 hours, the mixture is extracted three times with 500 ml of dichloromethane in each case. The combined organic phases are washed with sodium bicarbonate solution until neutral, dried over Na2 SO4 and filtered, and the filtrate is evaporated to dryness. Chromatographic purification (silica gel/dichloromethane) gives 20.53 g of 3-chloro-2,5-dibromopyridine. STR14 m.p.: 40°-41° C.

According to the analysis of related databases, 58236-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoechst Aktiengesellschaft; US5629428; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 886365-46-4

To a solution of Intermediate 12 (100 mg, 0.195 mmol) in N,N-dimethylformamide (1.0 mL) was added 5-chloro-3-methylpicolinic acid (43.6 mg, 0.254 mmol), (O-(7-azabenzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate) (111 mg, 0.293 mmol), and pyridine (0.047 mL, 0.586 mmol). The reaction was stirred at ambient temperature for 2 hours, and then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was redissolved in DCM (0.5 mL) and TFA (0.301 mL, 3.91 mmol) was added. The reaction was stirred at RT for an hour. The reaction was quenched with saturated aqueous sodium carbonate, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica-gel column chromatography, eluting with 0-50% (3:1 ethyl acetate:ethanol, 2% ammonium hydroxide) in heptanes, to provide the title compound (62 mg, 68.2% yield). 1H NMR (400 MHz, DMSO-d6) ppm 1.28-1.34 (m, 1H) 1.46 (s, 3H) 1.68-1.72 (m, 1H) 1.74 (s, 3H) 1.87-2.09 (m, 2H) 2.57 (s, 3H) 3.68 (d, J=5.77 Hz, 1H) 6.03 (br. s., 2H) 7.17 (dd, J=11.74, 8.90 Hz, 1H) 7.72-7.81 (m, 1H) 7.81-7.89 (m, 1H) 8.03 (dd, J=2.25, 0.68 Hz, 1H) 8.52-8.61 (m, 1H) 10.54 (s, 1H). LC/MS (ESI+) m/z=465.1 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 886365-46-4.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-41-6, 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. 131747-41-6, name is 2-(Trifluoromethyl)isonicotinic acid. A new synthetic method of this compound is introduced below.

A solution of 616 2-(trifluoromethyl)isonicotinic acid (10.0 g, 52.4 mmol) in 20 tetrahydrofuran (150mL) was cooled to 0 C., 1 mol/L 617 borane-tetrahydrofuran solution (105 mL, 105 mmol) was addedunder a nitrogen atmosphere and the mixture was stirred at 75 C. for 2 hr. The reaction mixture was pouredinto ice water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and driedover sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressureand the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the618 title compound ( 5.60 g , 31.6 mmol, 60%). MS (ESI) m/z 178 (M+H)+ 1H NMR (300 MHz, CDCl3): delta 8.68 (d, J=4.8 Hz, 1H), 7.79 (s, 1H), 7.64 (d, J=4.8 Hz, 1H) . 5.62 (br-s,1H), 4.66 (s, 2H),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131747-41-6, 2-(Trifluoromethyl)isonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; EA PHARMA CO., LTD.; KOBAYASHI, Kaori; SUZUKI, Tamotsu; KAWAHIRA, Mizuki; FUJII, Tomohiro; SUGIKI, Masayuki; OHSUMI, Koji; OKUZUMI, Tatsuya; (285 pag.)US2016/332999; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 29241-65-4 ,Some common heterocyclic compound, 29241-65-4, molecular formula is C6H3BrClNO2, 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.

Sulfuric acid (2 mL, 52.1 mmol) was added to the suspension of 5-bromo-2-chloronicotinic acid (1) (12.3 g, 52 mmol) was in methanol (100 mL). The mixture was stirred and refluxed for 15 hours. The solvent was evaporated and the residue was neutralized with saturated aqueous NaHC03(aq.). The result suspension was filtered and the solid was washed by water and dried by pump. Methyl 5-bromo-2-chloronicotinate (2) (11.6 g, 89 % yield) was afforded. NMR (400 MHz, CDCL) delta 8.53 (d, J = 2.4 Hz, 1H), 8.25 (d, J = 2.4 Hz, 1H), 3.93 (s, 3H). 13C NMR (101 MHz, CDCL) delta 163.58, 152.75, 148.61, 142.49, 127.64, 118.57, 53.10. ESI-MS m/z: 251.9 (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. 29241-65-4, 5-Bromo-2-chloronicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; ZHAO, Xue, Zhi; SMITH, Steven; METIFIOT, Mathieu, A.; JOHNSON, Barry; MARCHAND, Christophe; HUGHES, Stephen; POMMIER, Yves; BURKE, Terrence, R.; WO2014/186398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1206981-49-8, 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. 1206981-49-8, name is 3-(Trifluoromethoxy)pyridin-2-amine, molecular formula is C6H5F3N2O, 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 a solution of 3-(trifluoromethoxy)pyridin-2-amine (300 mg, 1.68 mmol) in dichloromethane (8 mL) was added N-bromosuccinimide (450 mg, 2.53 mmol) at 20 C. The reaction mixture was stirred at the same temperature for another 5 mm and subsequentlyconcentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 15% ethyl acetate in petroleum ether) affording product (220 mg, 5 1%): 1H NMR (400 MHz, DMSO-d6) oe: 8.03 (d, I = 2.0 Hz, 1H), 7.75 – 7.74 (m, 1H), 6.68 (brs, 2H).

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 1206981-49-8, 3-(Trifluoromethoxy)pyridin-2-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem