Pyridine-derivatives

Reference of 103058-87-3 ,Some common heterocyclic compound, 103058-87-3, molecular formula is C7H6BrNO2, 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.

5-Bromo-2-methoxynicotinaldehyde (472 mg, 2.18 mmol) and 1-methylpiperidin-4- amine (249 mg, 2.18 mmol) were stirred in methanol (10 mL). Acetic acid (0.12 mL) and sodium cyanoborohydride (137 mg, 2.18 mmol) were then added and the mixturewas stirred at room temperature for 22 h. The reaction mixture was evaporated under reduced pressure and the residue was partitioned between dichloromethane and a saturated aqueous sodium hydrogen carbonate solution. The phases were separated. The aqueous layer was extracted with dichloromethane. The combined organics were dried over anhydrous magnesium sulphate, filtered and evaporated under reducedpressure to give 647 mg (94% yield) of the title compound.LRMS (M+1): 314, 3161H NMR (400 MHz, Chloroform-d) 6 ppm 1.44 (2H, m), 1.88 (2H, m), 2.26 (3H, s), 2.43(1 H, m), 2.81 (2H, m), 3.73 (2H, s), 3.93 (3H, s), 7.69 (1 H, d, J = 2.4 Hz), 8.08 (1 H, d, J= 2.4 Hz)

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. 103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMIRALL, S.A.; GRACIA FERRER, Jordi; ERRA SOLA, Montserrat; WO2015/91532; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4487-56-3 , The common heterocyclic compound, 4487-56-3, name is 2,4-Dichloro-5-nitropyridine, molecular formula is C5H2Cl2N2O2, 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.

2,4-Difluoro-5-nitropyridine.In a 250 mL round-bottom flask was added 2,4- dichloro-5-nitropyridine (0.73 g,3.8 mmol), potassium fluoride (0.659 g, 11.3 mmol), and 18-crown-6 (0.160 g,0.605 mmol) in N-methylpyrrolidinone (3 mL) to give a tan suspension. Themixture was heated at 100C under nitrogen for 3 h. The mixture was thenpartitioned between water and ether/hexane. The organic layer was washed withwater, brine, dried and concentrated to give a tan solid (0.515 g, 85%): 1H NMR(400 MHz, CDC13) delta 9.07 (d, J = 9.7 Hz, 1H), 6.96 (dd, J = 9.5, 2.5 Hz,1H);19F NMR (376 MHz, CDC13) delta -52.20 (d, J = 29.3 Hz), -98.13 (d, J = 28.9 Hz).

The synthetic route of 4487-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, 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 73406-50-5.

Intermediate 8. S-Trifluoromethanesulfonyloxy-pyridine^-carboxylic acid ethyl ester.; To a stirred solution of 3-hydroxy-pyridine-2-carboxylic acid ethyl ester (3.06 g, 20.0 mmol) and Et3N (triethylamine) (5.58 ml_, 40.0 mmol) in CH2CI2 (100 mL) at minus150C was added a solution of Tf2O (trifluoromethanesulfonic anhydride) (4.04 mL, 24.0 mmol) in CH2CI2 (10 mL). The reaction was stirred at this temperature for 1 hour and then CH2CI2 (100 mL) was added followed by H2O. The layers were separated and the organic EPO layer was washed three times with 30 ml H2O and twice with 30 ml brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica chromatography using a gradient of hexanes:EtOAc (100:0) to hexanes-.EtOAc (75:25) to yield 13.3 g (74.52%) of Intermediate 8 as a yellow oil.

According to the analysis of related databases, 73406-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/31828; (2007); A2;,
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.62150-46-3, name is 4-Bromopicolinamide, molecular formula is C6H5BrN2O, molecular weight is 201.0207, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5BrN2O

EXAMPLE 64-((4-Oxo-3-o-tolyl-3,4-dihydropyrrolo[1 ,2-tf[1 ,2,4]triazin-2- yl)methylamino)picolinamideA mixture of 2-(aminomethyl)-3-o-tolylpyrrolo[1 ,2-7[1 .2,4]triazin-4(3H)-one (102 mg, 0.4 mmol), 4-bromopicolinamide (105 mg, 0.52 mmol) and DIEA (200 mu, 1 .13 mmol) in n- butanol (2.2 mL) was reacted under microwave irradiation at 190C during 22 h. After cooled to room temperature, the mixture was concentrated in vacuum and was purified by reverse phase chromatography (C-18 silica from Waters, water/1 :1 acetonitrile- methanol as eluents [0.1 % v/v formic acid buffered] 0% to 100%) to obtain 7 mg of the title compound (4,6%).LRMS (m/z): 375 (M+1 )+.1H NMR (400 MHz, DMSO) delta 8.38 (s, 2 H), 8.01 (d, J=5.86 Hz, 1 H), 7.90 (m, 1 H), 7.61 – 7.73 (m, 1 H), 7.48 – 7.58 (m, 1 H), 7.39 – 7.48 (m, 1 H), 7.23 – 7.40 (m, 2 H), 7.03 – 7.14 (m, 1 H), 6.93 – 7.04 (m, 1 H), 6.62 (dd, J=4.30, 2.74 Hz, 1 H), 6.38 – 6.53 (m, 1 H), 3.86 – 3.99 (m, 2 H), 2.08 (s, 3 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62150-46-3, 4-Bromopicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
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.628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, molecular weight is 175.55, as common compound, the synthetic route is as follows.Product Details of 628691-93-0

Step l :A suspension of 2-chloro-3-fluoropyridine-4-carboxylic acid (CAS 628691-93-0, 2 g, 11.39 mmol) in MeOH (7 mL) and DCM (21 mL) at 0 C was treated with TMS-Diazomethane (5.70 mL, 11.39 mmol) in a drop wise fashion. The reaction was stirred at 0 C for 0.5 h. The reaction was quenched with AcOH (0.5 mL) and concentrated in vacuo. The residue was purified by flash chromatography (0-100% EtOAc in petrol on Si02) to afford methyl 2-chloro-3-fluoropyridine-4-carboxylate. 1H NMR (300 MHz, Methanol-^) delta ppm 3.97 (s, 3 H) 7.76 – 7.86 (m, 1 H) 8.29 – 8.40 (m, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,628691-93-0, 2-Chloro-3-fluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; AHMED, Saleh; BARKER, Gregory; CANNING, Hannah; DAVENPORT, Richard; HARRISON, David; JENKINS, Kerry; LIVERMORE, David; WRIGHT, Susanne; KINSELLA, Natasha; (259 pag.)WO2016/148306; (2016); A1;,
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. 821791-58-6, name is Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

The following compounds were prepared as previously described with the addition of a chlorination step. An example of such a chlorination is described below. A mixture of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (1.00 g, 4.64 mmol) and NCS (0.68 g, 5.10 mmol) in DMF (30 mL) was stirred for 1 hour. The reaction mixture was diluted with EtOAc and washed with 0.1 N HCl solution. The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 1.10 g (95%) of 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester.

The synthetic route of 821791-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Marlow, Allison L.; Wallace, Eli; Seo, Jeongbeob; Lyssikatos, Joseph P.; Yang, Hong Woon; Blake, James; US2005/256123; (2005); A1;,
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 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 167837-43-6

The following compounds were obtained according to a similar manner to that of Example 2-(4). 2-[(E)-3-(6-Aminopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole. NMR (DMSO6, delta): 2.59 (3H, s), 4.00-4.10 (1H, m), 4.19-4.21 (1H, m), 5.32-5.45 (2H, m), 6.16-6.22 (2H, m), 6.29 (1H, d, J=16 Hz), 6.38-6.45 (2H, m), 6.48 (1H, d, J=8 Hz), 6.83-6.87 (1H, m), 7.11-7.23 (2H, m), 7.37-7.48 (2H, m), 7.48-7.58 (2H, m), 7.61 (1H, d, J=8 Hz), 7.70 (1H, d, J=8 Hz), 7.99-8.09 (2H, m), 8.20 (1H, d, J=8 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 167837-43-6.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6344462; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22353-40-8, 2,3-Dichloro-5-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, 22353-40-8, blongs to pyridine-derivatives compound. Recommanded Product: 22353-40-8

Anhydrous SnCl2 (300 g, 1.58 mol) and concentrated HCl (350 mL) were charged to a 5L flask with mechanical stirrer and thermocouple. The flask was cooled in ice and the product of Example 2B (100 g, 0.518 mol) was added in portions maintaining the temperature below 65 C. After the addition was complete, the cold bath was removed, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled in ice as 25% aqueous NaOH (1000 mL) was added to bring the mixture to pH>10. The mixture was extracted with CH2Cl2 (1*600 mL, 2*400 mL) and the combined extracts were washed with brine (200 mL), dried (MgSO4), and concentrated under vacuum. The residual solid was crystallized from a mixture of water (500 mL) and ethanol (100 mL) to provide the title compound as a solid. 1H NMR (CDCl3, 300 MHz) delta 3.80 (br s, 2H), 7.10 (d, J=3 Hz, 1H), 7.77 (d, J=3 Hz, 1H); MS (DCI/NH3) m/z 180/182/184 (M+NH4)+163/165/167 (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,22353-40-8, its application will become more common.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2004/242644; (2004); A1;,
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 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of (E)-3-(6-Aminopyridin-3-yl)acrylic acid

(1) To methanol (5 ml) in dry ice-acetone bath was added thionyl chloride (0.41 ml) dropwise over 5 minutes. After (E)-3-(6-Aminopyridin-3-yl)acrylic acid (700 mg) was added to the mixture, the reaction mixture was heated at reflux for 1 hour, and the solvent was removed under reduced pressure. The reaction mixture was adjusted to pH 8 with saturated sodium bicarbonate aqueous solution and extracted with dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The precipitate was collected by vacuum filtration and washed with isopropyl ether to give methyl (E)-3-(6-aminopyridin-3-yl)acrylate (725 mg) as a solid. mp: 173-175 C. NMR (DMSO-d6, delta): 3.67 (3H, s), 6.32 (1H, d, J=16 Hz), 6.45 (1H, d, J=8 Hz), 6.57 (2H, s), 7.51 (1H, d, J=16 Hz), 7.79 (1H, dd, J=2, 8 Hz), 8.15 (1H, d, J=2 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 167837-43-6.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5994368; (1999); A;,
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. 67310-56-9, name is 1-(5-Hydroxypyridin-2-yl)ethanone, the common compound, a new synthetic route is introduced below. Recommanded Product: 1-(5-Hydroxypyridin-2-yl)ethanone

A mixture of Example 28A (0.1 g, 0.235 mmol), l-(5-hydroxypyridin-2-yl)ethanone (0.065 g, 0.471 mmol), potassium carbonate (0.065 g, 0.471 mmol) and potassium iodide (2.73 mg, 0.016 mmol) in acetone (2.0 mL) was stirred at 140 C (0-450 W) in a Biotage Initiator microwave reactor for 45 minutes. The suspension was filtered, and the filtrate was concentrated. This residue and NaBH^ (0.089 g, 2.35 mmol) in methanol was stirred at ambient temperature overnight. The reaction mixture was concentrated, and the residue was purified by HPLC (10-85% acetonitrile in 0.1% trifluoroacetic acid/water at 25 mL/minute on aPhenomenex Luna CI 8 5 mupiiota 100 A AXIA column (250 mm x 21.2 mm)) to give 59 mg of the title compound as a white solid.JH NMR (400 MHz, DMSO-<) delta ppm 8.74 (d, / = 26.6 Hz, 2H), 8.30 (d, / = 2.8 Hz, 1H), 7.81 - 7.60 (m, 2H), 7.47 (t, / = 8.9 Hz, 1H), 7.05 (dd, / = 11.4, 2.8 Hz, 1H), 6.83 (ddd, / = 9.0, 2.9, 1.2 Hz, 1H), 4.85 (q, / = 6.5 Hz, 1H), 4.61 (s, 2H), 4.46 (s, 2H), 2.25 (s, 6H), 1.37 (d, / = 6.5 Hz, 3H). MS (ESI+) m/z 464.0 (M+H)+. The synthetic route of 67310-56-9 has been constantly updated, and we look forward to future research findings. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem