Day: March 16, 2022

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. 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, molecular formula is C12H9ClN2O3, 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. HPLC of Formula: C12H9ClN2O3

General procedure: 10%Pt/C (0.40 g, 0.2 mmol) was added to a suspension of the nitro derivative (2a-2d)(1.7 mmol) in methanol (50.0 mL). The reaction mixture was stirred underhydrogen atmosphere at room temperature overnight. The mixture was thenfiltered through celite and the filtrate was evaporated under reduced pressureto afford the desired amines (3a-3d).

With the rapid development of chemical substances, we look forward to future research findings about 179687-79-7.

Reference:
Article; Elkamhawy, Ahmed; Farag, Ahmed Karam; Viswanath, Ambily Nath Indu; Bedair, Tarek M.; Leem, Dong Gyu; Lee, Kyung-Tae; Pae, Ae Nim; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5147 – 5154;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 867279-13-8 , The common heterocyclic compound, 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine, molecular formula is C6H5BrClN, 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 stirred solution of 4-bromo-2-chloro-5-methylpyridine (2 g, 9.69 mmol, 1 equiv.) in t- BuOH (15 mL) was added t-BuONa (2.0 g, 20.34 mmol, 2.1 equiv.) at room temperature. The final reaction mixture was irradiated with microwave radiation for 5 h at 120 degrees C. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The reaction solution was acidified to pH 6 with HCl (aq.1M). The resulting mixture was extracted with CH2Cl2(3 x 50 mL). The combined organic layers were washed with brine (1×100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18 Column 330 g; Mobile Phase A: Water (10 mmol/L AcOH), Mobile Phase B: ACN; Flow rate: 80 mL/min; Gradient: 10% B to 30% B in 40 min; 254/220 nm) to afford 4- bromo-5-methylpyridin-2-ol(1.2g,65.89%) as an off-white solid.

The synthetic route of 867279-13-8 has been constantly updated, and we look forward to future research findings.

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

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. 403-45-2, name is 6-Fluoronicotinic acid, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Fluoronicotinic acid

A mixture of 6-fluoro-nicotinic acid (2.07g, 14.7mmol), K2CO3 (4.48g, 32.4mmol) and MeI (3.2Og, 22.5mmol) in DMF (6OmL) was stirred for 16h at rt. After dilution with H2O (5OmL), the reaction mixture was extracted with EtOAc (5OmL) and the extract washed successively with saturated NaHCO3 solution (2OmL), brine (2 x 2OmL) and dried (MgSO4). Filtration and evaporation of the solvent gave the product as an orange solid (1.79g, 78%). 1H (CDCl3) 8.53 (IH, s), 8.12 (IH, m), 6.77 (IH, dd), 3.67 (3H, s)

The synthetic route of 403-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JAMES BLACK FOUNDATION; WO2007/135350; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 183741-86-8, 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. 183741-86-8, name is 5-(Boc-amino)-2-methoxyisonicotinic Acid. A new synthetic method of this compound is introduced below.

[0615] Procedure: To a stirred solution of 5-((tert-butoxycarbonyl)amino)-2-methoxyisonicotinic acid (6.7 g, 24.974 mmol) in methanol / dichloromethane (6.7 mL / 67 mL) was added TMS-diazomethane (31.2 mL, 2.5 eq) at 0 C and the mixture was stirred at same temperature for 4 h. Reaction progress was monitored by TLC. Reaction mixture was concentrated, and residue was diluted with water, extracted using ethyl acetate (40 mL x 3), organic layer was dried over sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by gradient column chromatography using ethyl acetate in n-hexane to afford methyl 5-((tert-butoxycarbonyl)amino)-2-methoxyisonicotinate as off-white solid (4.5 g, 63.82 %).1HNMR (400 MHz, CDCl3): delta 9.24 (bs, 1H), 9.18 (s, 1H), 7.23 (s, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 1.52 (s, 9H). LC-MS (ES) m/z = 283.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183741-86-8, 5-(Boc-amino)-2-methoxyisonicotinic Acid, and friends who are interested can also refer to it.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 171197-80-1 ,Some common heterocyclic compound, 171197-80-1, molecular formula is C5H3FIN, 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.

Preparation 46; 5-Cyclopropyl-2-fluoro-pyridine; In a flask, combine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol), potassium phosphate (3.2 g, 15 mmol), and toluene-water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 hours. Dilute the mixture with chloroform-isopropanol (3: 1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 % ethyl acetate in hexane) to afford the title compound (430 mg, 63 %) as a pale yellow oil. 1H nuMR (400 MHz-CDCl3) delta 7.99 (d, J= 3 Hz, IH), 7.39 (td, J= 3, 5 Hz, IH), 6.79 (dd, J= 3, 8 Hz, IH), 0.96-1.02 (m, 2H), 0.63-0.69 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,171197-80-1, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1149-24-2, 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.1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, molecular weight is 251.28, as common compound, the synthetic route is as follows.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

The chemical industry reduces the impact on the environment during synthesis 1149-24-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153747-97-8, 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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.

Under nitrogen protection,Tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (202 mg, 0.59 mmol),N,N-bis(tert-butoxycarbonyl)-3-(1-(2,5-dichlorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3) ,2-Dioxaborolan-2-yl)pyridin-2-amine (300 mg, 0.49 mmol) andCesium carbonate (320mg, 0.98mmol)Ethylene glycol dimethyl ether/water (10 mL/1 mL)Pd(dppf)Cl2.CH2Cl2 (40 mg, 0.05 mmol) was added to the mixture.The reaction solution is heated to 90C.After stirring overnight, cool to room temperature and filter through celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 5/1) to give the title compound as a yellow oil (250 mg, 68%).

Statistics shows that 153747-97-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; (104 pag.)CN104650049; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89809-65-4, 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.89809-65-4, name is Methyl 6-Cyanopyridine-3-carboxylate, molecular formula is C8H6N2O2, molecular weight is 162.1454, as common compound, the synthetic route is as follows.

To a solution of methyl 5-(3-chlorobenzyl)pyridin-2-amine (0.262 g, 1 .2 mmol) in toluene (7 ml_) was added trimethylaluminum (0.6 ml_,1 .2 mmol, 2 M in toluene) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h before a solution of methyl 6-cyanonicotinate (0.162 g, 1 mmol) in toluene (2 ml_) was added. Reaction mixture was stirred at 100 0 C for 2 h under argon. The reaction solution was cooled to room temperature and quenched with methanol (5 ml_) and 1 N hydrochloric acid aqueous (5 ml_). The volatiles were concentrated, and the aqueous phase was extracted with dichloromethane (1 00 ml_ x 2). The combined organic layers were washed with brine (1 00 ml_), dried over sodium sulfate, filtered and concentrated. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified v/a prep-HPLC (Boston C18 21 *250 mm 10 pm column. The mobile phase was acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3-chlorobenzyl)pyridin-2-yl)-6-cyanonicotinamide (70 mg, 0.20 mmol, 20.8%) as a white solid. 1 H NMR (500 MHz, Dimethylsulfoxide-c/g) d 1 1 .33 (s, 1 H), 9.22 (d, J = 1 .3 Hz, 1 H), 8.53 (dd, J = 4.3, 2.5 Hz, 1 H), 8.36 (d, J = 2.0 Hz, 1 H), 8.20 (d, J = 8.0 Hz, 1 H), 8.12 (d, J = 8.5 Hz, 1 H), 7.75 (dd, J = 4.3, 2.5 Hz, 1 H), 7.35 – 7.32 (m, 2H), 7.28-7.23 (m, 2H), 3.99 (s, 2H); LCMS (ESI) m/z: 349.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 89809-65-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1116136-63-0 ,Some common heterocyclic compound, 1116136-63-0, molecular formula is C7H4ClN3O2, 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.

Into a 250 ml 3-necked roundbottom flask, was placed a solution of 5-chloro-3-nitro-1H- pyrrolo[3,2-b]pyridine (1.1 g, 5.56 mmol, 1.00 equiv) in 1,4-dioxane (30 ml). To this was added HCl (6mol/L) (15 ml, 90 mmol, 16.00 equiv). This was followed by the addition of a solution of Fe (2.5 g, 44.64 mmol, 8.00 equiv) in MeOH (50 ml). The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at reflux in a bath of oil. A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with H2O. Adjustment of the pH to 7-8 was accomplished by the addition of Na2CO3. The resulting solution was extracted three times with 100 ml of EtOAc and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 1.3 g (crude) of 5-chloro-1H-pyrrolo[3,2-b]pyridin-3-amine as a black solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1116136-63-0, its application will become more common.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2009/23844; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 550347-54-1 ,Some common heterocyclic compound, 550347-54-1, molecular formula is C6H5ClIN, 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 stirred solution of 2-chloro-5-iodo-4-methyl-pyridine (23. Og, 90.909mmol, 1 eq) in 1 ,2-dichloroethane (230ml_) was added NBS (24.3g, 136mmol, 1 .5eq) followed by addition of AIBN (6.0g, 36.4mmol, 0.4eq) at room temperature in dark. Resulting reaction mixture was heated at 80C for 16 hours. After maximum consumption of starting material, reaction mixture was cooled to room temperature and quenched with water (50ml_), extracted with DCM (3x50ml_). Combined organic phase was washed with brine (50ml_), dried over anhydrous Na2S04 and concentrated under reduced pressure to get dark brown semi solid (20g, crude). Crude of title compound was used as such for next reaction. LC-MS (m/z): No ionisation.

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. 550347-54-1, 2-Chloro-5-iodo-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZOETIS LLC; MENON, Sanjay; SHEEHAN, Susan M.K.; VAILLIANCOURT, Valerie A.; WO2014/39484; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem