Category: pyridine-derivatives

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.33252-63-0, name is 5-(Trifluoromethyl)pyridin-2-ol, molecular formula is C6H4F3NO, molecular weight is 163.1, as common compound, the synthetic route is as follows.Application In Synthesis of 5-(Trifluoromethyl)pyridin-2-ol

lambda/-bromosuccinimide (NBS, 39.0Og, 0.22 mol) is added portionwise to a solution of 5-(trifluoromethyl)pyridin-2-ol (30.0Og, 0.18 mol) in DMF (180 ml_), and the resulting mixture is stirred for 2 hours. The mixture is poured into water (1200 mL) and the precipitate was collected by filtration. The crystal is dried in vacuo to give the product as a white solid (1st crystal : 28.1Og). The filtrate is extracted with EtOAc, and the organic layer is concentrated.The residue is poured into water and the precipitate is collected by filtration. The crystal is dried in vacuo to give 3-bromo-5-(trifluoromethyl)pyridin-2-ol (2nd crystal : 9.65 g, total:37.75g, 85 % yield) as a yellow solid.1H-NMR (400MHz, CDCI3), delta (ppm): 7.86 (d, 1H), 8.02 (d, 1H), 13.17 (br, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-63-0, 5-(Trifluoromethyl)pyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/73934; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5418-51-9, 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 5418-51-9 as follows.

Step A: 2-(Difluoromethoxy)-5-nitropyridine To 2-hydroxy-5-nitropyridine (7 g, 50 mmol) in acetonitrile (500 mL) was added sodium sulfate (1.5 g, 10.6 mmol), and 2,2-difluoro-2-(fluorosulfonyl)acetic acid (6.2 mL, 60 mmol) and the reaction was allowed to stir at room temperature for 16 hours. The reaction was quenched with saturated aqueous sodium bicarbonate and the acetonitrile was removed in vacuo. The remaining aqueous component was extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The pale brown oily solid was triturated with ether/hexanes, filtered and the filtrate concentrated to afford 2-(difluoromethoxy)-5-nitropyridine (4.7 g, 24.7 mmol, 49% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.14 (d, J=2.76 Hz, 1H), 8.68 (dd, J=9.03, 2.76 Hz, 1H), 7.98 (s, 0.5H), 7.62 (s, 0.5H), 7.34 (d, J=9.03 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,5418-51-9, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/270405; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1235865-75-4, 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. 1235865-75-4, name is Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate. A new synthetic method of this compound is introduced below.

In 100mL2-Boc-octahydropyrrolyl [3,4-c] pyrrole (0.73 g, 3.4 mmol), 2-((1H-pyrrolo [2,3-b] pyridin-5-yl) oxy) -4-fluorobenzoic acidMethyl ester (1.00 g, 3.8 mmol), dipotassium hydrogen phosphate(2.28 g, 10 mmol) and 40 mL of DMSO were reacted at 130 C. for 6 h, cooled to room temperature, 50 mL of water and 30 mLEA, the layers were separated, the aqueous layer was extracted twice with 50 mL of EA, the combined organic phases were washed once with 50 mL of saturated brine,Dried over sodium sulfate, filtered and spin-dried to give 0.702 g of product in 43% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1235865-75-4, Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Sun Yat-sen University; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Kou Yuhui; Hu Bolin; Jiang Haigang; Ye Jiuyong; Liu Zhiqiang; Xie Hongming; Zhang Yingjun; Yan Ming; (39 pag.)CN106749233; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 123846-66-2, Adding some certain compound to certain chemical reactions, such as: 123846-66-2, name is 2-(5-Nitro-2-pyridinyl)acetonitrile,molecular formula is C7H5N3O2, 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 123846-66-2.

Sodium hydride (67.44 mmol) was added to a solution of 2-(5-nitropyridine-2-yl) acetonitrile (30.65 mmol) in dry THF (250 ml) at 0 C and the reaction mixture was stirred for 0.5 h. Methyl iodide (91.95 mmol) was added to the reaction mixture and reaction mixture was warmed to RT, stirred for another 24 h. Solvent was removed under vacuum; crude product was purified (silica gel column, EtOAc/hexane as eluent) to obtain the title compound. .H NMR (300 MHz, DMSO-d6): delta 9.43 (d, J=2.7 Hz, 1H), 8.55 (dd, J=8.7, 2.4 Hz, 1H), 7.86 (d, J = 8.7 Hz, 1H), 1.82 (s, 6H); MS (m/z): 192 (M+l)+.

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. 123846-66-2, 2-(5-Nitro-2-pyridinyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; KUMAR, Sanjay; SHARMA, Rajiv; ZAHLER, Robert; SAHU, Bichismita; AGARWAL, Veena, R.; NAIK, Nishigandha; WO2012/7926; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1462-86-8, 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. 1462-86-8, name is 3-Aminopicolinic acid. A new synthetic method of this compound is introduced below.

1. Reactions which are covered by Scheme 1; Example 1.1: Preparation of 2-amino-nicotinic acid methyl ester; To a solution of 3-amino-pyridine-2-carboxylic acid (1 g) in methanol (8 ml) and toluene (10 ml), under nitrogen atmosphere, was added a solution of (trimethylsilyl)- diazomethane (3.625 ml) (2M in diethylether). When the effervescence from the reaction had subsided a further portion of (trimethylsilyl)diazomethane (3.625 ml) (2M in diethylether) was added. The reaction mixture was stirred at ambient temperature for 20 hours. The reaction was quenched by addition of acetic acid (0.2 ml). The mixture was concentrated and the residue partitioned between dichloromethane and aqueous potassium carbonate (5% by weight). The phases were separated and the aqueous phase was extracted with further dichloromethane. The combined organic extracts were dried over magnesium sulfate and concentrated to give 2-amino-nicotinic acid methyl ester as a light yellow solid (968 mg). IH-NMR (400 MHz, CDCl3): 8.21-8.23 (m, IH), 8.12-8.14 (m, IH), 6.61-6.64 (m, IH), 3.89 (s, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1462-86-8, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2009/90401; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6959-47-3, Adding some certain compound to certain chemical reactions, such as: 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride,molecular formula is C6H7Cl2N, 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 6959-47-3.

General procedure: N-ethyl diamine (550 mg, 6.24 mmol) was dissolved inCH2Cl2 (10 mL). Chloromethyl pyryidine HCl salt (3.07 g, 18.71 mmol)was added followed by water (10 mL). Solution of NaOH in water (1.8 gin 6 mL) was added drop wise and the reaction mixture was stirred atRT for 3 days. Water (50 mL) was added and product was extracted withCH2Cl2 (3×20 mL), dried over MgSO4, solvent volume reduced to ca.10 mL under vacuum and transferred to short chromatographic columnand purified with EtOAc/MeOH gradient (0-30% MeOH). All productswere isolated as viscous orange oils

According to the analysis of related databases, 6959-47-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Schaefer-Ramadan, Stephanie; Barlog, Maciej; Roach, Jim; Al-Hashimi, Mohammed; Bazzi, Hassan S.; Machaca, Khaled; Bioorganic Chemistry; vol. 87; (2019); p. 366 – 372;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1603-40-3, 3-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, Product Details of 1603-40-3, blongs to pyridine-derivatives compound. Product Details of 1603-40-3

General procedure: 3-Chlorophenyl isothiocyanate and phenyl isothiocyanate (1.9 mmol and 3.7 mmol) was dissolved in 10 mL dichloromethane at 0 C. Then aniline (2.7 mmol and 5.5 mmol), was added dropwise with constant stirring, and completion of reaction is checked by TLC analysis. After 45 min a white solid appeared, the resultant solid product was filtered, washed with hexane, triturated with 10 mL of dichloromethane and excess of hexane and dried under vacuum. Recrystallization with methanol afforded the desired solid thiourea 1-38.

The synthetic route of 1603-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Khalid Mohammed; Naz, Farzana; Taha, Muhammad; Khan, Ajmal; Perveen, Shahnaz; Choudhary; Voelter, Wolfgang; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 314 – 323;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 573762-62-6, 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 573762-62-6 as follows.

0.8 g of 2-cyano-3-trifluoromethyl-5-aminopyridine was added to 20 ml of water.Stir vigorously,0.5 ml of thiophosgene was added dropwise over 30 minutes.After the addition, stirring was continued for 2 hours. The reaction mixture was extracted with chloroform (3×150 mL).The solid was filtered off, and the filtrate was evaporated to dryness under reduced pressure.I got ii-2 0.7 grams.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,573762-62-6, its application will become more common.

Reference:
Patent; Beijing Mei Bei Ta Pharmaceutical Co., Ltd.; Zhong Bohua; Fu Renfang; (10 pag.)CN109422725; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1480-65-5, 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 1480-65-5 as follows.

[0271] A mixture of 5-chloro-2-fluoropyridine (2 g, 15.21 mmol), N, N-dimethylformamide (40 mL), phenylmethanethiol (2 g, 16.10 mmol), and CS2CO3 (7.52 g, 23.08 mmol) was stirred for 16 h at room temperature. The resulting solution was stirred for 6 h at 60°C. The solids were filtered out. The residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1 : 10) to afford the title compound (3 g, 83.7percent) as colorless oil. LCMS [M+H+] 236.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-65-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; VERMA, Vishal; VOLGRAF, Matthew; HU, Baihua; (105 pag.)WO2018/29288; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-72-0 ,Some common heterocyclic compound, 1620-72-0, molecular formula is C7H6F3N, 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 solution of 2-methyl-6-(trifluoromethyl)pyridine (22.2 g, 138 mmol) in toluene (200 mL) was added mCPBA (23 g, 150 mmol). The reaction mixture was refluxed for 24 h under N2 atmosphere and quenched with saturated NH4CI solution. The resulting mixture was extracted with EtOAc (2 x 150 mL). The combined organic layers were washed with brine, dried over Na2S04, and concentrated in high vacuum. The residue was purified by silica gel chromatography (PE/EtOAc=5/l to 1/1) to give the title compound (5.5 g, yield : 22%); m/z (ES+) : 178 [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,1620-72-0, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; BLADH, Haakon; FELDING, Jakob; ZHOU, Ding; CAI, Zhen-wei; SØRENSEN, Morten Dahl; WO2015/24878; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem