Pyridine-derivatives

Electric Literature of 1235036-15-3, 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.1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate, molecular formula is C10H11BrClNO2, molecular weight is 292.56, as common compound, the synthetic route is as follows.

To a solution of Example 1.23.2 (12.3 g) and tert-butyl 3-bromo-6-chloropicolinate (5.9 g) in dioxane (50 mL) was added (lS,3R,5R,7S)-l,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8- phosphaadamantane(CyTop) (0.52 g) and bis(dibenzylideneacetone)palladium(0) (0.66 g). After several house vacuum/nitrogen refills, potassium phosphate (4.06 g) and water (25 mL) were added and the reaction was heated at 80 C under nitrogen for 30 minutes. The reaction was cooled and then water and ethyl acetate were added. The organic layer was separated and washed with brine. The combined aqueous layers were extracted with ethyl acetate, and dried over sodium sulfate. The solution was filtered, concentrated and chromatographed on silica gel using 33% ethyl acetate in heptanes to give the title compound.

The chemical industry reduces the impact on the environment during synthesis 1235036-15-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10128-72-0, 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 10128-72-0 as follows.

[0163] To a DMF (15 mL) solution of the chloride (300 mg, 1.5 mmol, 1.0 eq) and phenol (230 mg, 1.5 mmol, 1.0 eq) was added K2C03 (621 mg, 4.5 mmol, 3.0 eq) and the reaction mixture was heated at 80-90 C for 5 h. Solvent was removed and the residue was purified by column chromatography (EtOAc/ MeOH) to give the alkylation product. MS: exact mass calculated for C15H13N303, 283.10; mlz found, 284 [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,10128-72-0, its application will become more common.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102145; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 109613-97-0, name is 2-Bromo-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below., Safety of 2-Bromo-4-methoxypyridin-3-amine

To a solution of 2-bromo-4-methoxypyridin-3-amine (2.1 g, 10.34 mmol), N-(4-ethynylpyridin-2-yl)acetamide (1.82 g, 11.38 mmol) in DMF (15 mL) was added TEA (21.62 mL, 155 mmol) and CuI (0.12 g, 0.62 mmol). The reaction mixture was purged with nitrogen for 2 min, followed by addition of Pd(PPh3)2Cl2 (0.73 g, 1.03 mmol). The reaction mixture was then heated at 100 C. for 3 h. The reaction mixture was cooled down and diluted with ethyl acetate and saturated NaHCO3 solution. The organic layer (two times extracts) were combined, washed with saturated NaHCO3 solution, dried over MgSO4. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography. The product was eluted with DCM to 50% of 10% MeOH in DCM to give the desired product as a light yellow (1.0 g, 34%); HPLC: RT=0.48 min (H2O/ACN with 0.05% TFA, Waters Acquity SDS C18, 2.1×50 mm, 1.7-mum particles, gradient=1.8 min, wavelength=220 nm); MS (ES): m/z=283.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 10.59 (s, 1H), 8.34 (dd, J=5.1, 0.7 Hz, 1H), 8.22 (s, 1H), 7.79 (d, J=5.3 Hz, 1H), 7.34 (dd, J=5.2, 1.4 Hz, 1H), 6.91 (d, J=5.3 Hz, 1H), 5.35 (s, 2H), 4.03 (q, J=7.2 Hz, 1H), 3.88 (s, 3H), 2.11 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 109613-97-0, 2-Bromo-4-methoxypyridin-3-amine.

Reference:
Patent; Bristol-Myers Squibb Company; Fink, Brian E.; Zhao, Yufen; Borzilleri, Robert M.; Zhang, Liping; Kim, Kyoung S.; Kamau, Muthoni G.; Tebben, Andrew J.; (162 pag.)US2016/176871; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89466-17-1, 6-Bromo-5-methylpyridin-2-amine, 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, Safety of 6-Bromo-5-methylpyridin-2-amine, blongs to pyridine-derivatives compound. Safety of 6-Bromo-5-methylpyridin-2-amine

To a solution of 1 -(2,2-difluoro-l,3-benzodioxol-5-yl)cyclopropanecarboxylic acid (5g) in toluene (5OmL) and dimethylformamide (1 .25mL) was slowly added thionyl chloride(3.63mL) and the reaction mixture was stirred for about 3h at about 80C. The reaction mixture was concentrated under reduced pressure at about 50C. To the obtained residue in dichloromethane (lOmL) were added 6-amino-2-bromo-3-methylpyridine (3.86g) in dichloromethane (SOmL) and pyridine (SmL) at about room temperature. The reaction mixture was maintained for about 3h at about room temperature and water was added toit. The two layers were separated and the organic layer was treated with 10% hydrochloric acid solution and then with sodium bicarbonate solution. The organic layer was washed with water and brine solution, treated with charcoal, filtered, concentrated under reduced pressure at about 50C and was co-distilled with hexane. Hexane was added to the obtained residue and the mixture was stirred for about 6h. The solid obtainedwas filtered and dried at about 60C for about 8h. Yield: 65.3g (76%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89466-17-1, 6-Bromo-5-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; BHIRUD, Shekhar Bhaskar; KADAM, Suresh Mahadev; KANSAGRA, Bipin Parsottam; BHADANE, Shailendra Nilkanth; KALE, Shrikrishna Kantilal; PATIL, Ulhas Digambar; (57 pag.)WO2017/56031; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56946-65-7, Adding some certain compound to certain chemical reactions, such as: 56946-65-7, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine,molecular formula is C8H7Cl2N, 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.

A 25-mL round bottom flask was charged with 2,4-dichloro-6,7-dihydro-5H- cyclopenta[Z?]pyridine (0.300 g, 1.59 mmol), 5-chloro3-pyridinyl boronic acid (0.301 g, 1.91 mmol), tetrakis(triphenylphosphine)palladium(0) (0.092 g, 0.08 mmol), and CS2CO3 (1.56 g, 4.78 mmol). Toluene (8 ml), EtOH (2 ml) and water (4 ml) were added. The resulting mixture was stirred under Ar at 90 C for 2.5 h. After this time, the mixture was cooled to rt, filtered through celite, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on silica using hexane/ethyl acetate (10:0 to 0: 10) as eluent to afford the title compound (0.127 g, 30%) as a white solid. MW = 265.14. ]H NMR (CDC13, 500 MHz) delta 8.99 (d, / = 2.0 Hz, 1H), 8.59 (d, / = 2.5 Hz, 1H), 8.30 (t, / = 2.5 Hz, 1H), 7.50 (s, 1H), 3.15 (t, / = 7.5 Hz, 2H), 3.05 (t, / = 7.5 Hz, 2H), 2.21 (quin, / = 7.5 Hz, 2H).

According to the analysis of related databases, 56946-65-7, the application of this compound in the production field has become more and more popular.

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

Related Products of 128071-79-4, 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.128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine, molecular formula is C6H5BrFN, molecular weight is 190.013, as common compound, the synthetic route is as follows.

A mixture of 4-bromo-2-fluoro-3-picoline (1.90 g, 10 mmol, 1.0 eq), pyrazole (1.36 g, 20 mmol, 2.0 eq) and potassium carbonate (2.80 g, 20 mmol, 2.0 eq) in DMSO (20 mL, 0.5 M) was stirred at 70 C. After 16 h, the reaction mixture was added to brine and extracted with EtOAc (3x). The combined extracts were washed with brine, dried (MgS04), filtered and concentrated. The crude material was purified using chromatography on silica gel (0-50% EtO Ac/hexanes) to provide the title compound as a white crystalline solid (2.23 g, 94%). NMR (400 MHz, CDCl3) d 8.12 (d, J= 5.1 Hz, 1H), 8.09 (d, J= 2.2 Hz, 1H), 7.75 (d, J= 1.3 Hz, 1H), 7.51 (d, j= 5.2 Hz, 1H), 6.45 (dd, j= 2.3, 1.9 Hz, 1H), 2.56 (s, 3H). ES-MS [M+H]+ = 238.3.

The chemical industry reduces the impact on the environment during synthesis 128071-79-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P. Jeffrey; ENGERS, Darren W.; ENGERS, Julie L.; BENDER, Aaron M.; LONG, Madeline; (120 pag.)WO2019/241467; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2, 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 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Imidazo[l,2-a]pyridine-2-carboxylic acid (500 mg, 3.1 mmol) was dissolved in ethanol (20 ml) and platinium oxide (100 mg) was added, and the mixture hydrogenated at 4 bar overnight. The mixture was filtered, and the filtrate evaporated to dryness to afford the sub-title compound (500 mg, 97%). 1H NMR (400 MHz, DMSO-J6) delta 7.63 (s, IH), 3.96 (t, 2H), 2.70 (t, 2H), 1.85 (m, 4H).

According to the analysis of related databases, 64951-08-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/108750; (2007); 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.1346148-32-0, name is Methyl 5-fluoro-3-methylpicolinate, molecular formula is C8H8FNO2, molecular weight is 169.153, as common compound, the synthetic route is as follows.Recommanded Product: Methyl 5-fluoro-3-methylpicolinate

b) 5-Fluoro-3-methyl-pyridine-2-carboxylic acid To a solution of 5-fluoro-3-methyl-pyridine-2-carboxylic acid methyl ester (1.28 g) in MeOH (6 ml) was added at 22 C. a solution of lithium hydroxide mono hydrate (636 mg) in water (3 ml) and stiring was continued for 16 h. The mixture was diluted with water, the MeOH was evaporated at reduced pressure and the pH was adjusted to 1 using 1 N aqueous HCl. The aqueous layer was extracted with AcOEt, the organic layer was dried, evaporated and the residue was crystallized from AcOEt/n-heptane to give the title compound (1.02 g) as a pale yellow solid. MS: m/z=153.7 [M-H]-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1346148-32-0, Methyl 5-fluoro-3-methylpicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Banner, David; Guba, Wolfgang; Hilpert, Hans; Humm, Roland; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Rogers-Evans, Mark; Rombach, Didier; Woltering, Thomas; Wostl, Wolfgang; US2011/312937; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 94170-15-7, 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, 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, Quality Control of 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, blongs to pyridine-derivatives compound. Quality Control of 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde

Intermediate 1-10 (134.73 mg, 0.39 mmol) was dissolved in DCM (6 mL)4-Aldehyde-1-methylpyridine-2(1H)-one (64.2 mg, 0.468 mmol) and NaBH(OAc)3 (206.6 mg, 0.975 mmol),Stir at room temperatureThe reaction is complete,Add saturated aqueous sodium bicarbonate (5 mL),Extracted with DCM (3 x 10 mL),Combine the organic phase,Wash with water (2 × 5mL),Dry over anhydrous sodium sulfate,Filtered, concentrated,The crude product was purified by preparative HPLC to give a white solid(10.0 mg, yield: 5.5%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,94170-15-7, 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Wang Lin; Yang Xiaoju; Tian Yuwei; (46 pag.)CN108341819; (2018); 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.94170-15-7, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.Application In Synthesis of 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde

7-(1,1-dioxotetrahydro-2H-thiopyran-4-yl)-2-((3S,4S)-4-isobutylpyrrolidin-3-yl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (81.64 mg) was dissolved in DCM (4 mL).4-Aldehyde-1-methylpyridine-2(1H)-one (34.23 mg, 0.25 mmol) and sodium triacetoxyborohydride (110.2 mg, 0.52 mmol),Stir at room temperature overnight.TLC monitors the reaction completely,Add saturated aqueous sodium bicarbonate (5 mL),Extracted with DCM (3 x 10 mL),Organic phase merger,Washed (2 × 5mL),Dry over anhydrous sodium sulfate,filter,concentrate,The crude product was separated by preparative thin layer chromatography (DCM:MeOH = 10:1)A white solid 7-(1,1-dioxotetrahydro-2H-thiopyran-4-yl)-2-((3S,4S)-4-isobutyl-1-((1-methyl-) 2-oxo-1,2-dihydropyridin-4-yl)methyl)pyrrolidin-3-yl)pyrrolo[2,1-f][1,2,4]triazine-4(3H)-ketone(4.0 mg, yield: 3.7%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,94170-15-7, 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Wang Lin; Yang Xiaoju; Tian Yuwei; (46 pag.)CN108341819; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem