Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 60781-83-1, 4-Phenylpyridin-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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Add tri-tert-butylphosphine (4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium t-butoxide (52.7 g, 549 mmol) to 1-3 (30.83) A solution of g, 80.44 mmol) and 1-4 (13.69 g, 80.44 mmol) in degassed toluene (500 mL), and the mixture was heated under reflux for 2 hours.The reaction mixture was cooled to room temperature, diluted with toluene and filtered over EtOAc.The filtrate was diluted with water and extracted with toluene and the organic phases were combined and evaporated in vacuo. The residue was filtered through silica gel (heptane / dichloromethane) and crystallised from isopropyl alcohol.Intermediate 1-5 38.43 g was obtained in a yield of 81.32%.

The synthetic route of 60781-83-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhang Hong; Cai Hui; (28 pag.)CN108440524; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 637348-81-3, 3-Bromo-5-iodopyridin-2-ol, 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, Product Details of 637348-81-3, blongs to pyridine-derivatives compound. Product Details of 637348-81-3

Example 214b 3-Bromo-5-iodo-1-methylpyridin-2(1H)-one 214b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (50 mL), 214a (6.0 g, 20.0 mmol), iodomethane (4.26 g, 30.0 mmol), and K2CO3 (5.52 g, 40.0 mmol). The mixture was stirred at room temperature for 2 h and diluted with water (200 mL). The resulting white solid was collected by filtration to afford 214b (5.97 g, 95%) as a white solid. MS-ESI: [M+H]+ 314

At the same time, in my other blogs, there are other synthetic methods of this type of compound,637348-81-3, 3-Bromo-5-iodopyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74936-72-4, 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 74936-72-4 as follows.

(1) Preparation of (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl) -1,4-dihydropyridine-3-carboxylic acid (700g, 2.1mol) in methanol (14 L) was added Quinidine (617g, 1.90mol). The mixture was stirred at 90C under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for half an hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl -4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74936-72-4, its application will become more common.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 77199-09-8, 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.77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.

To a solution of 27 (20.0 g, 86.9 mmol) in DMF (100 mL) wereadded tributyl(vinyl)tin (28.1 mL, 95.6 mmol) and Pd(PPh3)4 (2.01 g, 1.74 mmol), and the mixture was stirred at 100 C for 2 hunder Ar atmosphere. The mixture was diluted with water(200 mL), and extracted with AcOEt (400 mL). The extracts werecombined, washed with brine (200 mL), dried over Na2SO4 andconcentrated in vacuo. The residue was purified by silica gel columnchromatography (hexane/AcOEt = 49/1 to 4/1) to give ethyl5-ethenylpyridine-2-carboxylate (16.5 g, quant.) as pale yellowoil. To a solution of obtained compound above (7.71 g, 43.5 mmol)in EtOH (77 mL) was added 10% Pd-C (1.54 g) and the mixture wasstirred at room temperature for 3 h under H2 atmosphere. The mixturewas filtered through membrane filter, and the filtrate was concentratedin vacuo to give the title compound (7.92 g, quant.) aspale yellow oil. 1H NMR (DMSO-d6) d 1.22 (3H, t, J = 7.6 Hz), 1.33(3H, t, J = 7.1 Hz), 2.71 (2H, q, J = 7.6 Hz), 4.33 (2H, q, J = 7.1 Hz),7.83 (1H, dd, J = 8.0, 2.2 Hz), 7.98 (1H, d, J = 8.0 Hz), 8.58 (1H, d,J = 2.2 Hz).

Statistics shows that 77199-09-8 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-bromopicolinate.

Reference:
Article; Ohashi, Tomohiro; Tanaka, Yuta; Shiokawa, Zenyu; Banno, Hiroshi; Tanaka, Toshio; Shibata, Sachio; Satoh, Yoshihiko; Yamakawa, Hiroko; Yamamoto, Yukiko; Hattori, Harumi; Kondo, Shigeru; Miyamoto, Maki; Tojo, Hideaki; Baba, Atsuo; Sasaki, Satoshi; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4777 – 4791;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1201676-03-0 ,Some common heterocyclic compound, 1201676-03-0, molecular formula is C7H4Cl2N2O, 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 mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (0.655 g, 3.23 mmol), triethylamine (2.61 g, 25.8 mmol), and 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3- a]pyrazine hydrochloride (0.544 g, 3.39 mmol) in dioxane (7.5 ml.) is stirred in a 48 ml_ sealed tube at 12O0C for 16 h. Additional 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine hydrochloride (0.500 g, 3.11 mmol) is added to the mixture, which is heated again at 12O0C for 24 h. A light yellow powder is isolated by filtration of the room temperature reaction mixture (0.61 1 g, 2.10 mmol, 65%). MS(ESI) m/z 291.18 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.1 1 (s, 1 H), 8.50 (s, 1 H), 7.01 (s, 1 H), 4.97 (s, 2 H), 4.68 (s, 2 H), 4.19 (t, J=5.31 Hz, 2 H), 4.01 (t, J=5.43 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1201676-03-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); 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 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5ClN2O2

A mixture of 6-chioro-2-methyi-3-nitropyridine(8.6() g, 50.00 mrnol), NH4Ci (27.00 g, 500.0() mrnol) and Fe (14.0() g, 250.00 mrnoi) in MeOK(100 mL) was stirred at 80 C for 5 11 The mixture was filtered and concentrated, and theresulting residue was purified by column chromatography (Si02. eluting with PE:EA 5:1) toafford the title compound.

With the rapid development of chemical substances, we look forward to future research findings about 22280-60-0.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADAMS, Gregory, L.; COX, Jason, M.; DEBENHAM, John, S.; EDMONDSON, Scott; GILBERT, Eric, J.; GUO, Yan; JIANG, Yu; JOSIEN, Hubert; KIM, Hyunjin, M.; LAN, Ping; MIAO, Shouwu; PLUMMER, Christopher, W.; RAJAGOPALAN, Murali; SHAH, Unmesh; SUN, Zhongxiang; TRUONG, Quang, T.; UJJAINWALLA, Feroze; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; SUZUKI, Takao; WANG, Nengxue; (182 pag.)WO2017/205193; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1040682-68-5, Adding some certain compound to certain chemical reactions, such as: 1040682-68-5, name is 1H-Pyrrolo[3,2-c]pyridine-4-carbonitrile,molecular formula is C8H5N3, 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 1040682-68-5.

To a solution of lH-pyrrolo[3,2-c]pyridine-4-carbonitrile (60.0 mg, 0.42 mmol , 1.0 eq), NIS (52.0 mg, 0.46 mmol, 1.1 eq) in DCM (4.0 mL) was stirred at rt for 2 h. After the reaction was complete, water was added, and the mixture was extracted with EA. The organic layer was washed with water, dried over Na2S04, filtered and concentrated. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide 3-iodo-lH-pyrrolo[3,2-c]pyridine-4-carbonitrile (160 mg, 97%).

According to the analysis of related databases, 1040682-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 23100-12-1, 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 23100-12-1, name is 6-Chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Preparation of tert-butyl 4-((6-chloropyridin-3-yl)methyl)piperazine-1-carboxylate To a solution of 6-chloronicotinaldehyde (0.5 g, 2.68 mmol) and tert-butyl piperazine-1-carboxylate (0.6 g. 3.22 mmol) in DCE was added acetic acid (0.1 mL) and the reaction was stirred for 2 h at RT. Then NaBH(OAc)3 (1.7 g, 8.1 mmol) was added to the reaction portion-wise at RT. The reaction was stirred at RT for 16 hours. The reaction mixture was then concentrated. The crude material was dissolved in water and basified to pH 8-9 using saturated aqueous NaHCO3 solution. The mixture was extracted with EtOAc (2*25 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by preparative HPLC to afford tert-butyl 4-((6-chloropyridin-3-yl)methyl)piperazine-1-carboxylate (300 mg, 31% yield).

According to the analysis of related databases, 23100-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; DALES, Natalie; GORMISKY, Paul; KERRIGAN, John Ryan; SHU, Lei; (159 pag.)US2019/77773; (2019); 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 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

To compound 12 (50 mg, 0.27 mmol) and 2-aminophenol (35 mg, 0.32 mmol) was added a 1N aqueous sodium hydroxide solution (0.75 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. It was then diluted with water and extracted twice with ethyl acetate. 4N HCl solution was added (pH 4), and the mixture was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate, and the solvent was evaporated. The residue was purified by preparative HPLC to yield 52 mg (82%) of the title compound as a tan solid. 1H NMR (400 MHz, DMSO-d6): delta 7.44-7.52 (m, 3H), 7.89 (t, J=8.4Hz, 2H), 8.71 (d, J=4.4Hz, 1H), 8.76 (d, J=8.1Hz, 1H), 14.42 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 111.0, 113.3, 118.9, 119.8, 125.0, 125.8, 130.4, 131.9, 141.1, 149.5, 150.1, 152.3, 157.4. HRMS m/z calcd for C13H8N4O: 236.0698; found: 236.0698.

With the rapid development of chemical substances, we look forward to future research findings about 956010-87-0.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 144657-66-9, 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. 144657-66-9, name is tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, molecular formula is C13H14N2O3, 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 l-(fer?-butyloxycarbonyl)-3-formyl-7-azaindole (Int-16, 9.8 g, 40 mmol) and sodium borohydride (1.7 g, 44 mmol) in methanol (50 mL) were stirred at rt for 4 h. TLC showed the reaction was complete. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water, brine, dried, concentrated, and purified by flash column chromatography to afford alcohol Int-17 (8.4 g, 85%).

According to the analysis of related databases, 144657-66-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCEPION PHARMACEUTICALS, INC.; JIANG, Shan; XING, Xinglong; WANG, Qishan; KONG, Ren; WO2011/23081; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem