Category: pyridine-derivatives

Related Products of 794592-13-5, 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. 794592-13-5, name is Ethyl 5-bromo-3-methylpicolinate, molecular formula is C9H10BrNO2, 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.

To A solution of ethyl 5-bromo-3-methylpyridine-2-carboxylate (1.6 G ; 6. 95 mmol) and benzoyl peroxide (84. 23 mg ; 0. 347 mmol) in carbon tetrachloride (20 ML) was added N-BROMOSUCCINIMIDE (2.47 G ; 13. 91 mmol). The reaction mixture was heated at reflux for 3 h. Another equivalent of N-bromosuccinimide and benzoyl peroxide (85 mg) was added and refluxing was continued for a further 7 h. Reaction was monitored by MS. After 10 h the product was the major peak. The reaction mixture was allowed to cool, filtered through celite washed with carbon tetrachloride. The filtrate was evaporated under reduced pressure to give an oil, 2.7 g. The oil (2.7 g ; 6.9615 mmol) and hydrazine hydrate (2.4 mL) in ethanol was heated at reflux overnight. The solvent was evaporated under reduced pressure, the residue was taken-up in water acidified with 2N HCl the solid obtained was collected by filtration washed with water and dried by azeotroping with toluene. Yield = 0.9 g. The crude product and phosphorus oxychloride were heated at 60 for 1 h. The excess phosphorus oxychloride was evaporated under reduced pressure to give 3-BROMO-8-CHLOROPYRIDO [2, 3-D] PYRIDAZINE (0.97 g) as solid. This material was azeotroped with toluene and then treated with 4- aminobenzotrifluoride (0.64 g, 0.495 mL ; 3. 97 mmol) in 1, 4-dioxane (20ml) and heated at 40 for 1 h. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and sodium carbonate solution. The ethyl acetate extracts were combined, washed with brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was purified by flash chromatography using a gradient of (90->50%) ISO- HEXANE/ETHYL acetate. The appropriate fractions were combined and evaporated under reduced pressure to give 3-BROMO-N-(4-(TRIFLUOROMETHYL) PHENYL) PYRIDO [2, 3- D] PYRIDAZIN-8-AMINE (100 MG). H NMR (500 MHz, DMSO-D6) 8 : 7.73 (2H, d, J8. 6 Hz), 8.41 (2H, d, J8. 8 Hz), 8.91 (1H, d, J2.2 Hz), 9.25 (1H, s), 9.33 (1H, d, J2.2 Hz), 10.05 (1H, s). The amine was reacted as in Example 4 to give the title COMPOUND. LH NMR (500 MHz, DMSO-d6) 8 : 2.49 (3H, s), 7.49 (1H, dd, J4.8 and 7.7 Hz), 7.76 (2H, d, J8.6 HZ), 7.90 (1H, dd, J0. 5 and 7.1 Hz), 8.47 (2H, d, J8. 6 Hz), 8. 66 (1H, dd, J0. 5 and 4.2 Hz), 8. 80 (1H, d, J2.0 Hz), 9.39 (1H, s), 9.48 (1H, d, J2.0 Hz), 10.10 (1H, s) ; MS (ES M+1) 382

According to the analysis of related databases, 794592-13-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/99177; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7251-52-7 ,Some common heterocyclic compound, 7251-52-7, molecular formula is C13H12N2O, 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.

d) (RS)-Phenyl-pyridin-2-yl-acetamide (0.340 g, 1.60 mmol) was dissolved in 5 ml of a saturated solution of HCl/methanol and refluxed for 6 h in a closed vessel. The mixture is poured on 25 g of ice, the pH is adjusted to 8-9 by cautious addition of 28% sodium hydroxide solution keeping the temperature below 10 C. and the product is extracted with ethyl acetate/water. After drying (MgSO4) and concentration, the crude material is purified by flash chromatography on silicagel using 1:4 mixture of ethyl acetate and hexane as eluant to yield 0.204 g (0.939 mmol, 59%) of (RS)-phenyl-pyridin-2-yl-acetic acid methyl ester as a white solid, m.p. 74 C. and MS: m/e=228.2 (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,7251-52-7, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US6548522; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 133627-45-9, 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. 133627-45-9, name is 2-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, 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.

A mixture of 2-chloro-4-methylpyridin-3-amine (1.0 g, 7.0 mmol) and concentrated hydrochloric acid (4.4 mL) was cooled to 0 C and a solution of sodium nitrite (0.5 g, 7.5 mmol) in water (8 mL) was added dropwise. The mixture was stirred for 1 hour at 0 C and then was added dropwise to a stirred solution of potassium iodide (1.6 g, 9.6 mmol) in water (9 mL). The mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with diethyl ether and the organic phase was washed with aqueous sodium thiosulphate, brine, dried (MgSO4) and evaporated in vacuo. The crude product was recrystallized from hexane to give the title compound (0.88 g, 47%) as a white solid. LRMS (m/z): 254 (M+1)+. 1H-NMR delta (CDCl3): 2.50 (s, 3H), 7.05 (d, J=4.9 Hz, 1 H), 8.15 (d, J=4.9 Hz, 1 H).

According to the analysis of related databases, 133627-45-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 504413-35-8, N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide, 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, name: N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide, blongs to pyridine-derivatives compound. name: N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide

A mixture of A81-3 (15 g, crude, 46 mmol) in 1 N NaOH/EtOH (50 mL/40 mL) was stirred at 80C overnight. After cooled to r.t., the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2S04 and the solvent was removed by vacuum. The residue was recrystallized in petroleum ether to give a brown solid (8.3 g, 85%). H NMR (400 MHz, DMSO-d<5) delta 8.60 (s, 1H), 7.32 -7.05 (m, 2H), 7.00 (s, 1H), 5.22 (s, 2H). The synthetic route of 504413-35-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ZHANG, Xiaohu; ACCRO BIOSCIENCE INC.; MA, Haikuo; ZHENG, Jiyue; HE, Sudan; (95 pag.)WO2018/17435; (2018); 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.848366-28-9, name is 5-Bromo-3-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-3-chloro-2-methoxypyridine

To a glass vial was added 4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (WO 2008/130481 , p 47) (0.273 g, 1.65 mmol), 5-bromo-3-chloro-2-methoxypyridine (0.368 g, 1.65 mmol), sodium ferf-butoxide (318 mg, 3.31 mmol), diacetoxypalladium (0.037 g, 0.17 mmol), X-Phos (0.079 g, 0.17 mmol) and anhydrous toluene / ferf-butanol, 5 /1 (6 mL). The vial was flushed with a stream of argon for 15 sec and capped. The mixture was heated with stirring for 2h at 1 10C then allowed to cool to room temperature and stirred at rt for 5 days. Diluted with CH2CI2 (10 mL) and water (2 mL), filtered through a celite pad. The organic phase was separated by filtering through a phase separation tube and concentrated in vacuo. Purified by flash chromatography on silica gel with heptane / EtOAc 100 / 0 to 0/ 100 to give 6-(5-chloro-6-methoxy-pyridin-3-yl)-4-methoxy-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine as a yellow solid (95 mg, 19% yield) LCMS: [M+H]+=307.0 / 308.9, Rt (3)= 1.62 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,848366-28-9, 5-Bromo-3-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 53937-02-3 , The common heterocyclic compound, 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone, molecular formula is C12H11NO2, 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 suspension of 4-(benzyloxy)pyridin-2(lH)-one (426 mg, 2.12 mmol), tert-hvXy 7-bromo-9-tosyl-3,4-dihydro-l/f-pyrido[3,4-delta]indole-2(9H)-carboxylate (1.28 g, 2.54 mmol), CuI (484 mg, 2.54 mmol), 8-hydroxyquinoline (369 mg, 2.54 mmol) and Cs2COs (760 mg, 2.33 mmol) in DMSO (10 mL) was degassed under reduced pressure for 45 min. Attorney’s Docket 2882.023BThe suspension was put under Ar and heated at 135 0C with stirring for 1.5 h. The suspension was cooled, 4:1 CH2C12/(9:1 MeOH/NH4OH) (50 niL) was added and the resulting suspension was stirred at 25 0C for 10 min. The suspension was passed through a plug of silica gel and the filtrate was washed with brine. The solution was dried over Na2SO4 and concentrated under reduced pressure to afford an amorphous solid. Flash chromatography (silica gel, (1 :1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH) 100:0 to 0:100) yielded the title compound (715 mg, 54%) as an off-white solid: 1H NMR (300 MHz, CDCl3) delta 8.18 (br s, IH), 7.82-7.73 (m, 2H), 7.48-7.35 (m, 6H), 7.33-7.23 (m, 4H), 6.12-5.97 (m, 2H) 5.07 (s, 2H), 4.90 (br s, 2H), 3.72-3.64 (m, 2H), 2.73-2.63 (m, 2H), 2.34 (s, 3H), 1.51 (s, 9H).

The synthetic route of 53937-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 139022-25-6 , The common heterocyclic compound, 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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 suspension of imidazo[1 ,2-a]pyridine-6-carboxylic acid (1 g, 6.2 mmol) in dioxane (12 ml) the title compound of Preparation 1 (0.91 g, 6.2 mmol) was added. To the suspension thus obtained POCI3 (1.73 ml, 18.6 mmol) was added dropwise at room temperature. The mixture was stirred at 70C for 3h under inert atmosphere. It was poured onto a mixture of a 2M aqueous solution of sodium hydroxide (50 ml) and ice (50 ml). The solid obtained was filtered, washed and dried to yield 792 mg (47%) of the title compound.LRMS: m/z 274 (M+1)+ Retention time: 2.08min (method A)1H NMR (200 MHz, DMSO-d6) delta ppm 0.98(t, J=8 Hz, 3H), 1.46(m, 2H), 1.69(m, 2H), 3.41 (t, J=8Hz, 2H), 5.48 (brs, 1 H), 7.65(m, 4H), 8.64(s, 1 H)

The synthetic route of 139022-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; GRIMA POVEDA1 Pedro Manuel; AGUILAR IZQUIERDO, Nuria; MIR CEPEDA Marta; CARRASCAL RIERA, Marta; TERRICABRAS BELART, Emma; WO2011/69647; (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. 134896-35-8, name is 3-Nitro-2-phenylpyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C11H8N2O2

Step 2 cis-2-Phenyl-3-aminopiperidine A solution of 30 g (0.15 mol) of 2-phenyl-3-nitropyridine in 190 mL of methanol was hydrogenated using 5 g of platinum oxide with an initial pressure of 45 psi hydrogen. After 2 h, 50 mL of conc HCl was added, the vessel repressurized to 45 psi, and the reduction continued for an additional 6.25 h. The reaction was diluted with water (100 mL) and filtered. Three reactions were combined at this point and the combined cake washed with methanol (200 mL), water (100 mL), methanol (200 mL), water (100 mL), and methanol (200 mL). The filtrate was concentrated, the residue treated with 500 mL of 5N NaOH and extracted with ether (3*1 L) and methylene chloride (2*1 L). The combined extracts were dried with sodium sulfate, filtered and the filtrate concentrated to afford 80.9 g of a pale yellow oil. Chromatography (5 kg Silica Gel 60, 70-230 mesh, methylene chloride/methanol/ammonium hydroxide 92.5:7.5:0.75) afforded 62 g (78% yield) of cis-2-phenyl-3-aminopiperidine as a pale yellow oil: 1H NMR (CDCl3) delta 1.35-1.55 (m, 4H), 1.65-1.98 (m, 3H), 2.75 (m, 1H), 2.95 (m, 1H), 3.17 (m, 1H), 3.8 (bs, 1H), 7.19-7.37 (m, 5H). MS (EI) m/z 176.

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, 134896-35-8, 3-Nitro-2-phenylpyridine.

Reference:
Patent; Merck & Co., Inc.; US6241964; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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: To a solution of 6-methoxy-2-pyridinecarboxaldehyde (1.0 eq) in THF (0.05 M) was added dropwise ArMgBr (1.0 M in Et2O, 1.2 eq) at ?78 °C. After stirring at ?78 °C for 1 h, the reaction mixture was quenched by 1 N HCl and extracted with EtOAc. A combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc/hexanes).

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. 54221-96-4, 6-Methoxypicolinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fei, Xiang; Yuan, Yue; Lee, Young-Mi; Jeong, Kwang Won; Seo, Seung-Yong; Bulletin of the Korean Chemical Society; vol. 35; 8; (2014); p. 2547 – 2550;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

From thieno[3,2-b]pyridin-7-ol (300 mg, 2.00 mmol) and POBr3 (2.80 g, 10.0 mmol) and the mixture was heated at 65 C for 6 h. After cooling, NaOH (aq) (5 mL), water (5 mL) and chloroform (5 mL) were added. The phases were separated and the aqueous phase was extracted with more chloroform (2 * 5 mL). The organic phase was dried (MgSO4) and filtered. Removal of the solvent gave compound 1as a yellow solid (363 mg, 85%), m.p. 67-68 C. 1H NMR (400 MHz, CDCl3): delta 7.46 (1H, d, J = 5.2 Hz, 6-H), 7.67 (1H, d, J = 5.6 Hz, HetAr-H), 7.83 (1H, d, J = 5.6 Hz, HetAr-H), 8.51 (1H, d, J = 5.2 Hz, 5-H) ppm. 13C NMR (100.6 MHz, CDCl3): delta 121.7 (6-CH), 125.9 (CH), 126.9 (C), 131.4 (CH), 135.7 (C), 147.5 (5-CH), 156.4 (C) ppm. HRMS (EI-TOF): calcd for C7H479BrNS [M]+ 212.9248. Found 212.9248. Calcd for C7H481BrNS [M]+ 214.9227. Found 214.9227.

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, 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one.

Reference:
Article; Queiroz, Maria-Joao R.P.; Peixoto, Daniela; Calhelha, Ricardo C.; Soares, Pedro; Dos Santos, Tiago; Lima, Raquel T.; Campos, Joana F.; Abreu, Rui M.V.; Ferreira, Isabel C.F.R.; Vasconcelos, M. Helena; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 855 – 862;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem