Month: April 2022

Reference of 1026796-81-5, 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.1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

Step 2: N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide To a mixture of N-(4-bromopyridin-2-yl)acetamide (17.2 g, 80 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (26.4 g, 104 mmol), Pd(dppf)Cl2 (11.7 g, 16 mmol) and KOAc (23.6 g, 240 mmol) under an atmosphere of nitrogen was added anhydrous DMF (1500 mL). The mixture was allowed to stir at 80 C. for 3.5 h. The solvent was removed and the residue was diluted with EtOAc (1000 mL). Activated carbon (100 g) was added. The slurry was heated at reflux for 5 min and then filtered. The organic solution was concentrated and the residue was recrystallized from EtOAc to give N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (6.1 g, 29%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 1.29 (s, 12H), 2.09 (s, 3H), 7.24 (dd, J=6.0, 1.2 Hz, 1H), 8.30-8.33 (m, 2H), 10.47 (br s, 1H).

Statistics shows that 1026796-81-5 is playing an increasingly important role. we look forward to future research findings about N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89510-90-7, 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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine. A new synthetic method of this compound is introduced below.

4-Amino-2-chloro-5-fluoropyridine (0.77 g, 4.7 mmol) was carefully added to 7.5 niL of concentrated sulfuric acid at 0-5 C (ice-bath) with stirring to give a solution. Potassium nitrate (1.1 g, 10 mmol) was gradually added to the solution during a period of 10 min while the internal temperature was maintained below 5 C. The reaction mixture was further stirred at 0-5 C for 1 hr and at room temperature for 10 min when TLC showed that all starting material had disappeared and a new product was formed. The mixture was carefully poured onto 30 g of crushed ice. The resulting solution was extracted with methylene chloride (2 x 20 mL). Combined organics were dried, filtered, and concentrated to give the crude product (0.56 g, yield: 61 %), which was directly carried to the next step without purification. LCMS(ESI) m/z: 192.6 [M+H+].Step 5 : 2-Chloro-5-fluoro-4-nitroaminopyridine (560 mg, 2.9 mmol) was carefully added to4.5 mL of concentrated sulfuric acid. The mixture was stirred at room temperature for 12 hrs when TLC showed that the starting material had disappeared and a new product had formed. The mixture was then poured onto 11 g of crushed ice with stirring. The resulting solution was mixed with 20 mL of methylene chloride and neutralized by dropwise addition of 28% ammonium hydroxide with stirring while the internal temperature was maintained below 5 C in a salted ice bath. The organic layer was separated and the aqueous layer was extracted with methylene chloride (2 x 20 mL). The combined organic extracts were dried over MgS04, filtered, evaporated in vacuo to give the crude product (450 mg, yield: 80%), which was carried to the next step without purification. LCMS(ESI) m/z: 192.6 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LAI, Yingjie; LIANG, Jun; MAGNUSON, Steven R.; TSUI, Vickie H.; ZHANG, Birong; ROBARGE, Kirk; WO2011/113802; (2011); A2;,
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. 89488-30-2, name is 5-Bromo-3-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-3-methylpyridin-2(1H)-one

Example 509 5-{1-[2-(Difluoromethoxy)benzyl]-2-methyl-1H-benzimidazol-6-yl}-3-methylpyridin-2(1H)-one To Intermediate 57 (140 mg, 0.34 mmol) were added 5-bromo-3-methylpyridin-2-ol (76 mg, 0.41 mmol), Pd(PPh3)4 (20 mg, 0.016 mmol), 2M aqueous Na2CO3 solution (2 mL) and 1,4-dioxane (10 mL). The reaction mixture was stirred at 105 C. for 4 h. Further Pd(PPh3)4 (20 mg, 0.016 mmol) and Na2CO3 solution (1 mL) were added and the reaction mixture was stirred at 105 C. overnight. The reaction mixture was cooled to ambient temperature, diluted with water (1 mL) and extracted with ethyl acetate (2*20 mL). The combined organic layers were concentrated in vacuo and the crude residue was purified by silica flash column chromatography (0-10% MeOH/DCM) and then by preparative HPLC to yield, after freeze-drying, the title compound (3 mg, 2%) as a white solid. deltaH (d6-DMSO) 11.59-11.25 (1H, br s), 7.72 (1H, d, J 1.4 Hz), 7.63-7.49 (3H, m), 7.40-7.33 (3H, m), 7.26 (1H, d, J 7.6 Hz), 7.16-7.11 (1H, m), 6.68-6.65 (1H, m), 5.52 (2H, s), 2.45 (3H, s), 2.00 (3H, s). LCMS (pH 3) 396.8, MH+, RT 1.33 minutes, 100% UV. LCMS (pH 10) 396.8, MH+, RT 1.66 minutes, 100% UV.

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, 89488-30-2, 5-Bromo-3-methylpyridin-2(1H)-one.

Reference:
Patent; Brookings, Daniel Christopher; Calmiano, Mark Daniel; Gallimore, Ellen Olivia; Horsley, Helen Tracey; Hutchings, Martin Clive; Johnson, James Andrew; Kroeplien, Boris; Lecomte, Fabien Claude; Lowe, Martin Alexander; Norman, Timothy John; Porter, John Robert; Quincey, Joanna Rachel; Reuberson, James Thomas; Selby, Matthew Duncan; Shaw, Michael Alan; Zhu, Zhaoning; Foley, Anne Marie; US2015/152065; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109613-97-0, 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 109613-97-0 as follows.

To an ice-cold solution of 2-bromo-4-methoxypyridin-3-amine (Intermediate 38), (2.74 g) in pyridine (102 mL) was added ethyl chloroformate (1.91 mL) dropwise and then stirred at rt for 45 min. The reaction mixture was cooled in an ice-bath and more ethyl chloroformate (9 mL) added and the mixture left to stir overnight at rt. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over MgSO4, filtered and evaporated under vacuum to give a solid. Product was observed in the aqueous layer by LC-MS, so this was re-extracted with EtOAc (3*) and evaporated under vacuum to give a solid which was combined with the previous solid, dissolved in DCM and purified by column chromatography (normal phase, 50 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 10-70% EtOAc in n-hexane) to give the desired product (2.35 g). LCMS: m/z 275.43 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.32 (t, J=7.1 Hz, 3H) 3.93 (s, 3H) 4.24 (q, J=7.1 Hz, 2H) 6.06 (br. s., 1H) 6.86 (d, J=5.6 Hz, 1H) 8.19 (d, J=5.6 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109613-97-0, its application will become more common.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 766557-60-2, 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. 766557-60-2, name is 2-Ethoxy-3-iodopyridine, molecular formula is C7H8INO, 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.

An excess of saturated ammonium chloride solution was added, followed by ethyl acetate, the mixture being stirred for 5 minutes. The aqueous phase was separated off and extracted with ethyl acetate (2*). The combined organic phases were washed with water (2*), and the solvent was removed in vacuo. During this, unreacted 5-iodoisatin precipitated first from the still dilute solution and was separated off. After further concentration, finally the title compound also crystallized. The suspension was stored in a refrigerator at 5 C. for 2 hours. The precipitated, pale yellow solid was then filtered off and washed with a little ethyl acetate. After drying at 40 C., (±)-3-(2-ethoxypyridin-3-yl)-3-hydroxy-5-iodo-1,3-dihydro-2H-indol-2-one (17.1 g, 43.16 mmol, 57%) was isolated. ESI-MS [M+H+]=397.05 calculated for C15H13IN2O3=396.19

According to the analysis of related databases, 766557-60-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abott GmbH & Co KG; US2011/65720; (2011); 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. 23612-36-4, name is 3-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below., Computed Properties of C7H5BrN2

To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert- butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol). After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HC1 (25, 10 mL) and brine. The organic layer was dried (Na2S04), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90%). MS (ESI+) m/z = 299 (M+H)+.

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, 23612-36-4, 3-Bromo-1H-pyrrolo[3,2-c]pyridine.

Reference:
Patent; Proximagen Limited; EVANS, David; CARLEY, Allison; STEWART, Alison; HIGGINBOTTOM, Michael; SAVORY, Edward; SIMPSON, Iain; NILSSON, Marianne; HARALDSSON, Martin; NORDLING, Erik; KOOLMEISTER, Tobias; WO2011/113798; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 76015-11-7 ,Some common heterocyclic compound, 76015-11-7, molecular formula is C7H9NO2, 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.

REFERENCE EXAMPLE 2 3-Methoxy-2-methyl-4(1H)-pyridone (5.6 g) was suspended in phosphorus oxychloride (50 ml), refluxed for 10 hours, and concentrated. To the resultant residue was added toluene and the residual phosphorus oxychloride was evaporated under reduced pressure. To the resultant oily substance were added chloroform and water and the chloroform layer was separated. The aqueous layer was made alkaline with potassium carbonate and extracted with chloroform. The chloroform solutions thus obtained were combined, washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, to give 4-chloro-3-methoxy-2-methylpyridine (4.8 g) as a light brown oil. NMR(CDCl3) delta: 2.53(3H, s), 3.84(3H, s), 7.14(1H, d, J=6 Hz), 8.12(1H, d, J=6 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76015-11-7, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4738975; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73583-41-2, 4-Bromo-3-chloropyridine, 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, 73583-41-2, blongs to pyridine-derivatives compound. Recommanded Product: 4-Bromo-3-chloropyridine

Step c: To a solution of tert-butyl (i-(6-amino-5-mercaptopyrazin-2-yl)-4-methylpiperidin-4-yl)carbamate(44 mg, 0.130 mmol), 4-bromo-3-chloropyridine (31.2 mg, 0.162 mmol), XantPhos (7.5 mg, 0.013 mmol), and Pd2 (dba)3 (5.9 mg, 0.0065 mmol) in dioxane (2 mL) was added (at RT and under N2) DIPEA (68 IL, 0.389 mmol). The resulting solution was stirred in a microwave reactor for 1 h at 110 C. and for 1 h at 125 C. After cooling to RT, the reaction was diluted with EtOAc and it was filtered through a pad of Celite followed by EtOAc (5 mL) wash. The volatiles were removed under reduced pressure. The result-ing residue was dissolved in DCM (3 mE) and it was treated with TFA (500 IL). The resulting mixture was stirred for 10 mm at RT. The volatiles were removed under reduced pressure and the resulting residue was purified by HPLC (gradient elution 15-40% acetonitrile in water, 5 mM NH4OH modifier) to give 6-(4-amino-4-methylpiperidin-1 – yl)-3-((3-chloropyridin-4-yl)thio)pyrazin-2-amine (8.5 mg, 0.024 mmol). ?H NMR (400 MHz, METHANOL-d4) oe 8.30 (s, 1H), 8.06 (d, J=5.56 Hz, 1H), 7.52 (s, 1H), 6.58 (d, J=5.31 Hz, 1H), 3.76 (ddd, J=13.64, 7.07, 4.29 Hz, 2H), 3.44-3.59 (m, 2H), 1.45-1.64 (m, 4H), 1.09-1.23 (m, 3H). HRMS calcd for C,5H2QC1N65 (M+H) 351.1159. found 351.1159. IC50 is 0.076 tM.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-41-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; Chen, Zhuoliang; Dore, Michael; Fortanet, Jorge Garcia; Karki, Rajesh; Kato, Mitsunori; LaMarche, Matthew J.; Perez, Lawrence Blas; Williams, Sarah; Sendzik, Martin; (63 pag.)US2017/1975; (2017); 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.1214328-96-7, name is Methyl 3-bromo-6-chloropicolinate, molecular formula is C7H5BrClNO2, molecular weight is 250.48, as common compound, the synthetic route is as follows.Formula: C7H5BrClNO2

B) methyl 6-chloro-3-((E)-2-ethoxyvinyl)pyridine-2-carboxylate To a mixture of methyl 3-bromo-6-chloropyridine-2-carboxylate (2.00 g) in acetonitrile (30 mL) and water (20 mL) were added 2-((E)-2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.42 g), tripotassium phosphate (3.39 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (328 mg) and palladium(II) acetate (90 mg), and the mixture was stirred under nitrogen atmosphere at 60C for 2 hr. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate, and the insoluble substance was removed by filtration. The filtrate was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (560 mg). 1H NMR (400 MHz, DMSO-d6) delta 1.28 (3H, t, J = 7.6 Hz), 3.88 (3H, s), 3.90-4.00 (2H, m), 6.27 (1H, d, J = 12.8 Hz), 7.43 (1H, d, J = 12.8 Hz), 7.60 (1H, d, J = 8.8 Hz), 8.16 (1H, d, J = 8.8 Hz) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214328-96-7, Methyl 3-bromo-6-chloropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOGO, Takatoshi; YOSHIKAWA, Masato; SAITOH, Morihisa; KATOH, Taisuke; SEKI, Tomohiro; NAKADA, Yoshihisa; (148 pag.)EP3366684; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1189434-55-6, 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 1189434-55-6 as follows.

[0149] A mixture of 67.2 mL of acetic anhydride and 28.8 mL of formic acid was heated at 50-60 C oil bath temperature for 3 h and then cooled to rt to give formic-acetic anhydride, which was then slowly added into the solid ethyl 2-(aminomethyl)-3-pyridinecarboxylate HCland then stirred at rt for 8 h. Excess reagent was evaporated to give a residue, which was neutralized by very slow addition of sat NaHCC>3 solution. Solution was extracted with DCM, dried and evaporated to provide imidazo[l,5-a]pyridine as a yellow solid.MS: exact mass calculated for C10H10N2O2, 190.07; m/z found, 191 [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,1189434-55-6, 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; WO2013/102142; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem