Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 5632-81-5, 2-Chloropyridine-3,5-diamine, 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, 5632-81-5, blongs to pyridine-derivatives compound. COA of Formula: C5H6ClN3

REFERENCE EXAMPLE 18 Synthesis of ethyl 3-[(5-amino-6-chloropyridin-3-yl)amino]-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate To 1.4 g of ethyl 3-chloro-2,4,5-trifluorobenzoyl-acetate were added 1.5 g of acetic anhydride and 1.5 g of triethyl orthoformate, and the mixture was heated under reflux for 2 hours. The solvent was distilled off, and toluene was added to the residue for azeotropic distillation. 3 ml of chloroform was added to the half of the residue, and a solution of 360 mg of 3,5-diamino-2-chloropyridine in 3 ml ethanol was added dropwise to the mixture at room temperature and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off, and the residue was purified by column chromatography to obtain 200 mg of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5632-81-5, its application will become more common.

Reference:
Patent; Wakunaga Pharmaceuticals Co., Ltd.; US5998436; (1999); 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.882033-66-1, name is 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4ClFN2, molecular weight is 170.5715, as common compound, the synthetic route is as follows.Quality Control of 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Example 224A mixture of 4-chloro-5-fluoro-lH-pyrrolo [2, 3-b] pyridine (30 mg) , 3-piperidinecarboxamide (45 mg) and N,N-diisopropylethylamine (30 muL) inDMI(0.4mL) was heated in the microwave reactor (2000C, 2 hours) . The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (10 mL) and half-saturated aqueous sodium hydrogencarbonate (10 mL) . The aqueous phase was extracted with EtOAc(2x 10 mL) and combined organic layers were washed with brine (20 mL) , dried over MgSO4, and concentrated. Purification of the crude product by preparative silica gel thin-layer chromatography (EtOAc) gave 1- (5-fluoro-lH-pyrrolo [2, 3-b]pyridin-4-yl) -3- EPO piperidinecarboxamide (5 mgj as a pale brown solid.1H-NMR(DMSO-d) delta : 11.5 (IH, s) , 7.96 (lH,d, J=5.7Hz) , 7.38 (IH, s) , 7.33 (1H,d, J=3.0Hz) , 6.87 (IH, s), 6.49 (IH, d, J=3.0Hz) , 3.82-3.70 (2H,m) ,3.21-3.06 (2H,m), 2.52-2.44 (IH,m) , 1.94-1.52 (4H,m) . ? MS(ESI) :m/z 263(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,882033-66-1, 4-Chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); 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. 136818-50-3, name is 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, the common compound, a new synthetic route is introduced below. Product Details of 136818-50-3

To the stirred solution of lH-pyrrolo[2,3-b]pyridine-2-carboxylic acid (5, 2.5 g, 15.4 mmol) and Nu,Omicron-dimethylhydroxylamine hydrochloride (6, 1.8 g, 18.5 mmol in DCM (50 mL), was added triethylamine (10.6 mL, 77.1 mmol), HOBt (3.54 g, 23.14 mmol) followed by EDC.HC1 (4.42 g, 23.18 mmol) at 0C and the reaction mixture was stirred at room temperature for 16h. The reaction mixture was cooled to room temperature, filtered through celite and evaporated the filtrate. To the crude, added water (10 mL) and compound was extracted with DCM (30mL). Organic layer was dried over sodium sulfate and evaporated to get crude product. The crude residue was purified by gradient column chromatography using silica gel and eluent 2-4% MeOH in DCM to afford the product as off white solid. (Yield: 82%, 2.6 g). MS (ESI): mass calcd. for CioHnN302, 205.09; m/z found, 206.1 (M+H)+.

The synthetic route of 136818-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; HALLUR, Gurulingappa; DURAISWAMY, Athisayamani Jeyaraj; PURRA, Buchi Reddy; RAO, N.V.S.K.; RAJAGOPAL, Sridharan; (247 pag.)WO2019/58393; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 200064-11-5, 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. 200064-11-5, name is 4-(5-Bromo-2-pyridyl)morpholine. A new synthetic method of this compound is introduced below.

Under the protection of nitrogen, CuI (1 mmol), Cs2CO3 (20 mmol) and ethyl 2-oxocyclohexylcarboxylate (2 mmol) were added to DMSO (10 mL).Stir at room temperature for 30 min.5-hydroxy-3-methoxy-4-phenylquinolin-2(1H)-one (10 mmol) and 4-(5-bromopyridin-2-yl)morpholine (10 mmol) in DMSO (12 mL) solution, added by injection.Heat to 100 C overnight. Cool to room temperature, filter, add water (50 mL) and dichloromethane (50 mL×3) and collect organics.The solvent was evaporated under reduced pressure, and the crude material was purified by column chromatography to give 5-hydroxy-3-methoxy-1-(6-morpholinylpyridin-3-yl)-4-phenylquinolin-2 (1H) -ketone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,200064-11-5, its application will become more common.

Reference:
Patent; Ocean University of China; Shao Changlun; (69 pag.)CN108658937; (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.930093-72-4, name is 4-Chloro-5-methyl-6-((2-methylpyridin-3-yl)oxy)pyrimidine, molecular formula is C11H10ClN3O, molecular weight is 235.6696, as common compound, the synthetic route is as follows.Product Details of 930093-72-4

A solution of KOBut (2.4 mL, 1.0 M in THF, 2.34 mmol) was added to a solution of alcohol 50B (0.42 g, 1.95 mmol) and the chloride IB (0.56 g, 2.39 mmol) in anhydrous THF (10 mL) under nitrogen at 0 C and stirred at 0 C to room temperature for 16 hours. The reaction was quenched with saturated NH4Cl solution (15 mL) and extracted with EtOAc (30 mL * 3). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified on a silica gel column (ISCO) with MeOH (NiH3) in dichloromethane (0-»5%) to provide compound 158 (0.81 g, 99% yield). LCMS: 416.5

At the same time, in my other blogs, there are other synthetic methods of this type of compound,930093-72-4, 4-Chloro-5-methyl-6-((2-methylpyridin-3-yl)oxy)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2009/55331; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 145100-50-1 ,Some common heterocyclic compound, 145100-50-1, molecular formula is C7H4F6N2O4S2, 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.

Step C: Preparation of (1S)-1-(4-fluorophenyl)-3-[(3R,4S)-1-(4-{3-[methyl(methylsulfonyl)-amino]propyl}phenyl)-2-oxo-4-(4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)azetidin-3-yl]propyl acetate (i-10b wherein R10=CH3) Guanidine (13 mg, 0.13 mmol) was added to a mixture of the intermediate from Step B (82 mg, 0.13 mmol) and triethylamine (18 muL, 0.13 mmol) in methanol (2 mL). After 3 h, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo to afford a clear oil which was dissolved in CH2Cl2 (1.5 mL). Triethylamine (24 mL, 0.17 mmol), DMAP (2.0 mg, 0.016 mmol) and (bis(trifluoromethylsulfonyl)amino)pyridine (77 mg, 0.13 mmol) were added successively to the above solution. After 3 h, the reaction was quenched with 0.5N aq. HCl and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 35%-40% EtOAc/hexanes as eluent) afforded the title compound. m/z (ES) 655 (M-OAc)+. 1H-NMR (500 MHz, CDCl3) delta: 7.43 (d, J=8.6 Hz, 1H), 7.32-7.28 (m, 2H), 7.15 (d, J=6.4 Hz, 1H), 7.10 (d, J=8.4 Hz, 1H), 7.04 (t, J=6.5 Hz, 1H), 5.72 (t, 6.6 Hz, 1H), 4.66 (d, J=2.3 Hz, 1H), 3.14 (dt, J=2.6, 6.6 Hz, 2H), 3.08 (dt, J=2.5, 8.2 Hz, 1H), 2.84 (s, 3H), 2.79 (s, 3H), 2.61 (t, 7.7 Hz, 2H), 2.08 (overlapped s, 3H), 2.09-2.04 (m, 2H), 1.93-1.84 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145100-50-1, its application will become more common.

Reference:
Patent; DeVita, Robert J.; Morriello, Gregori J.; Lin, Peter; US2007/78098; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-00-7 , The common heterocyclic compound, 17282-00-7, name is 3-Bromo-5-methylpyridin-2-amine, molecular formula is C6H7BrN2, 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.

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 17282-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72830-09-2, 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. 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride. A new synthetic method of this compound is introduced below.

Examples; Starting compounds and intermediates; 2-(3,4-Dimethoxy-pyridine-2-ylmethylsulfanyl)-5-methoxy-3H-imidazo[4,5-b]pyridine A reaction mixture of 10.00 g (55.20 mmol) 5-methoxy-3H-imidazo[4,5-b]pyridine-2-thiol and 12.37 g (55.20 mmol) 2-chloromethyl-3,4-dimethoxy pyridinium chloride in isopropanol (200 ml) is stirred for 2 h under reflux. The mixture is concentrated, filtered and dried at 60C for 16 h. Afterwards the crude hydrochloride of the product is suspended in a mixture of water dichloromethane and is basified to pH 8 by adding sodium hydroxide solution (6 N). The mixture is extracted with dichloromethane three times. The combined organic layers are washed with water, dried over calcium chloride, concentrated in vacuo, reslurried in acetone and dried again in vacuo to give 14.76 g (44.4 mmol / 80 %) of the title product with a melting point of 157.0C (acetone).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride, and friends who are interested can also refer to it.

Reference:
Patent; ALTANA PHARMA AG; WO2005/105799; (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 56700-70-0, name is tert-Butyl pyridin-3-ylcarbamate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 56700-70-0

In heat-dried argon purged 4-neck flask was placed a solution of pyridin-3-yl-carbamic acid tert-butyl ester (10 g, 51.5 mmol, CAS RN 56700-70-0) in THF (100 mL). After cooling down to -75 C., tert-butyllithium (1.7M solution in n-pentane, 66.6 mL, 113 mmol) was added dropwise over 15 min keeping the temperature below -60 C. The resulting light brown suspension was stirred at -75 C. for 3.75 h. A solution of iodine (28.7 g, 113 mmol) in THF (50 mL) was added dropwise over 20 min. below -63 C. The reaction mixture was stirred at -75 C. for 1.5 h and then poured on saturated aqueous NH4Cl solution (1000 mL) and EtOAc (500 mL). The layers were separated. The organic layer was washed once with 10% aqueous Na2S2O3 solution (300 mL) and once with brine (250 mL), dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 120 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Yellow solid (11.7 g; 71%). MS (ESI): m/z=321.1 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 56700-70-0.

Reference:
Patent; Bissantz, Caterina; Dehmlow, Henrietta; Erickson, Shawn David; Karnachi, Prabha Saba; Kim, Kyungjin; Martin, Rainer E.; Mattei, Patrizio; Sander, Ulrike Obst; Pietranico-Cole, Sherrie Lynn; Richter, Hans; Ullmer, Christoph; US2012/232051; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1990-90-5 , The common heterocyclic compound, 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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.

A total of 20.628 mg (0.1 mmol) of S-IBU and 10.814mg (0.1 mmol) of 3M4AP were dissolved in methanol-H2O (3:1, v: v) and left for slow evaporation at ambient conditions. Good quality single crystals were obtained for SCXRD after 10 days

The synthetic route of 1990-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Dejia; Pei, Tiezhu; Bai, Yunhe; Zhou, Lina; Bao, Ying; Yin, Qiuxiang; Xie, Chuang; Journal of Molecular Structure; vol. 1179; (2019); p. 487 – 494;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem