Pyridine-derivatives

Application of 52378-63-9 , The common heterocyclic compound, 52378-63-9, name is (3-Aminopyridin-2-yl)methanol, molecular formula is C6H8N2O, 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.

0.5 mmol of 3-amino-2-hydroxymethylpyridine was added to the schlenk tube,0.5 millimoles of phenethyl alcohol, 0.5 millimoles of potassium t-butoxide,0.005 mmol dodecacarbonyltrisodium,0.015 mmol of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene and 1.2 ml of t-amyl alcohol were charged, protected with N2, and the mixture was stirred at 130 C for 10 hours.Stop heating and stirring, cooled to room temperature, diluted reaction solution, filtered,The solvent was distilled off under reduced pressure and the residue was purified by column chromatography to obtain the target product. The column eluant was a petroleum ether: ethyl acetate mixed solvent with a volume ratio of 12: 1, and the yield was 46%.

The synthetic route of 52378-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South China University of Technology; Zhang Min; Xiong Biao; (19 pag.)CN104876929; (2016); B;,
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. 161117-83-5, name is tert-Butyl (2-methoxypyridin-3-yl)carbamate, the common compound, a new synthetic route is introduced below. SDS of cas: 161117-83-5

Under a nitrogen atmosphere, the entire batch of compound II in tetrahydrofuran solution, 70.2 tetramethylethylenediamine (0.6 mol, 1.5 eq) was added to the reaction flask.The temperature was lowered to -30 C, and 263.4 g of n-butyl lithium n-hexane solution (0.96 mol, 2.4 eq) was added dropwise. After the dropwise addition, the reaction was incubated for 2 hours.After the heat preservation was completed, 92.7 g of N-formylmorpholine (0.8 mol, 2.0 eq) was added and stirred for 30 min.After the reaction is completed, the temperature is controlled at 0-20 C, the pH value is adjusted to 5-7 with 3N hydrochloric acid, the layers are separated, 200g of methylene chloride is added to the aqueous phase, and extraction is performed once.Combine the organic phases, concentrate under reduced pressure until a large amount of solid precipitates, add 300g of n-heptane,After steaming to a certain volume, beating and filtering, 81.3 g of yellow solid (80% yield in two steps) is obtained as compound III.

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheng Da Pharmaceutical Co., Ltd.; Shi Yuhua; Qian Wei; Feng Yu; Huang Xing; Dang Junkui; Wang Zhipeng; Dong Changming; Xu Hong; Huang Zongxi; Chen Ye; Shen Huafei; Zhang Jun; (12 pag.)CN110964011; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 113293-70-2, 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 113293-70-2 as follows.

2,6-dichloroisonicotinaldehyde (25.3 g, 144 mmol) in toluene (205 mL)as well asethylene glycolTo a solution in (12.06 mL, 216 mmol),p-Toluenesulfonic acid monohydrate (0.54 g, 2.87 mmol) was added in one portion.The reaction was heated to reflux using a Dean-Stark trap apparatus for 16 hours.Cool the reaction to room temperature,Add 200 mL of ethyl acetate,Quenched by addition of aqueous NaHCO3. Separate the layers,The aqueous phase was extracted with ethyl acetate (2 × 20 mL). The combined organic extracts are then washed once more with NaHCO3,Dried over MgSO4, filtered and concentrated.The product was purified by silica gel chromatography eluting with 5-40% ethyl acetate: heptane,The product (24.8 g, 78% yield) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59105-50-9, 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.59105-50-9, name is (5-Bromopyridin-3-yl)(phenyl)methanone, molecular formula is C12H8BrNO, molecular weight is 262.1, as common compound, the synthetic route is as follows.

The 3-bromo-5-benzoyl-pyridine (270 mg, 1 . 0mmol), potassium thioacetic acid (183 mg, 1 . 61mmol) dissolved in dioxane (10 ml), add DIPEA (0.36 ml, 2 . 1mmol), after the replacement Ar gas, adding Pd2(dba)3, (23.8 mg, 0 . 026mmol), Xantphos (30 mg, 0 . 052mmol), Ar gas replacement again 3 times, the temperature is increased to 100 C reflux reaction 10h.The filtrate was washed with ethyl acetate, combined with ethyl acetate and filtrate, evaporated to dryness and the residue was purified by silica gel column chromatography to give an orange-red oil (116 mg, 45%).

Statistics shows that 59105-50-9 is playing an increasingly important role. we look forward to future research findings about (5-Bromopyridin-3-yl)(phenyl)methanone.

Reference:
Patent; Chinese Academy of Sciences, Shanghai Institute of Materia Medica; Nanjing Changao Pharmaceutical Technology Co., LTD; YANG, YU SHE; LING, CHEN YU; FU, LI QIANG; LI, ZHAN; (49 pag.)CN103626693; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1034467-27-0 , The common heterocyclic compound, 1034467-27-0, name is 2-Fluoro-4-iodo-5-(methoxymethoxy)pyridine, molecular formula is C7H7FINO2, 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.

Preparation 19; 6-Fluoro-4-iodo-pyridin-3 -ol; Add HCl (3 M in water, 31 mL, 93.01 mmol) to a solution of 2-fluoro-4-iodo-5- methoxymethoxy-pyridine (3.9 g, 13.78 mmol) in THF (20 mL). Stir the mixture at 60 0C for 3 hours. Cool down the mixture. Adjust the pH to 7 with slow addition of saturated aqueous sodium bicarbonate solution. Extract the solution with ethyl acetate three times. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to afford the title compound (3.2 g, 97.18 %) as a yellow solid. MS (EI) m/z 240 [M+l]+.

The synthetic route of 1034467-27-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); 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. 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Hydroxymethyl)-4-nitropyridine

A 200-mL round-bottomed flask was charged with n-butanol (50 mL) and NaH (2.12 g, 53.57 mmol) and stirred at 0 C under inert atmosphere for 1 h. After, (4~nitropyndin-2~yl)methanol (1.0 g, 6.5 mmol) was added to the stirring reaction mixture. The resulting reaction mixture was refluxed for 20 h. After this period, the reaction mixture was cooled with an ice bath, quenched with saturated aqueous NFUC and concentrated in vacuo. The resulting reside was extracted with EtOAc (3 c 75 mL). The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The crude material purified by flash chromatography (80 to 100% EtOAc in hexanes) on silica gel (55 mL) to afford (4- butoxypyridin-2-yl)methanol (599 mg, 51 % yield) as a brown oil.

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, 98197-88-7, 2-(Hydroxymethyl)-4-nitropyridine.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; KOIDE, Kazunori; BEIN, Kiflai; BRESSIN, Robert, Kruger; BURROWS, James, Proviano; GAMBINO, Adriana; LEIKAUF, George, D.; PHAM, Dianne; (80 pag.)WO2020/27905; (2020); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 386704-05-8, 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 386704-05-8, name is 2-Chloro-6-(trifluoromethyl)nicotinamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6 Preparation of 3-amino-2-chloro-6-trifluoromethylpyridine To a mixture of 200 g of 2-chloro-6-trifluoromethylnicotinamide and 1,000 ml of water, 432 ml of a 11.6 wt% aqueous sodium hypochlorite solution and 190 ml of a 10 N aqueous sodium hydroxide solution were dropwise added in order under cooling with ice, followed by stirring at 90C for 30 minutes. The reaction mixture was cooled to 10C, crystals precipitated were collected by filtration, washed three times with 100 ml of cooled water, and then dried at room temperature for 24 hours to obtain 144 g of 3-amino-2-chloro-6-trifluoromethylpyridine (melting point: 96 to 97C). 1H-NMR(CDCl3) delta= 4.47(2H, bs, NH2), 7.09(1H, d, J= 7.8 Hz), 7.42(1H, d, J= 7.8 Hz).

According to the analysis of related databases, 386704-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP2251329; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 161117-83-5, 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 161117-83-5 as follows.

Under a nitrogen atmosphere, a whole batch of compound II in tetrahydrofuran solution, 93.6 g of tetramethylethylenediamine (0.8 mol, 2.0 eq) was added to the reaction flask.Cool to -78 , add 261.1g n-butyl lithium n-hexane solution (0.96mol, 2.4eq) dropwise,After the dropwise addition, the reaction was kept for 2 hours.After the heat preservation is completed, the temperature is controlled to -40 C, 58.9 g of N-N-dimethylformamide (0.8 mol, 2.0 eq) is added, and the mixture is stirred for 30 min.After the reaction is completed, the temperature is controlled at 0-20 C, the pH value is adjusted to 5-7 with 3N hydrochloric acid, the layers are separated, 200g of methylene chloride is added to the aqueous phase, and extraction is performed once.Combine the organic phases, concentrate under reduced pressure until a large amount of solid precipitates, add 300g of n-heptane and steam to a certain volume.Beating and filtering to obtain 79.3g of yellow solid (78% yield in two steps) is compound III.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,161117-83-5, its application will become more common.

Reference:
Patent; Cheng Da Pharmaceutical Co., Ltd.; Shi Yuhua; Qian Wei; Feng Yu; Huang Xing; Dang Junkui; Wang Zhipeng; Dong Changming; Xu Hong; Huang Zongxi; Chen Ye; Shen Huafei; Zhang Jun; (12 pag.)CN110964011; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1220910-89-3 , The common heterocyclic compound, 1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, molecular formula is C21H17FN6O2, 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 the kettle was added tetrahydrofuran (20 L)And benzyl N- [3-fluoro-4- [6- (2-methyl- 2H- tetrazolium- 5 -yl) -3-pyridyl] phenyl] carbamateCompound (II) (1 Kg, 2.47 mol),0 ~ 30 C After mixing,1,3-Dimethyl-3,4,5,6-tetrahydro-2-pyrimidone was added sequentially (DMPU, 0.63 Kg, 4.94 mol, 2 equivalents),Lithium tert-butoxide (0.396 Kg, 4.94 mol, 2 equivalents)Add R-glycidyl butyrate(0.39 Kg, 2.72 mol, 1.1 equivalents)0 ~ 30 C for 15 hours.After the reaction,The reaction was quenched by adding a mass-volume ammonium chloride solution (1 Kg / 10 L)Concentrated under reduced pressure,The residue was added to methanol (10 L)Stirred for 0.5 hours to give suction filtration,The filter cake was washed with methanol,45 ~ 50 C under vacuum to give a white solid(5R) -3- (4- (6- (2-methyl- 2H- tetrazolium- 5-yl) -3-pyridyl) -3- fluorophenyl) -5-hydroxymethyl oxazoline -2-one Compound (III) (0.87 Kg, yield: 95%).

The synthetic route of 1220910-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing You Ke Pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Group Co., Ltd.; Li Shang; Che Xiaoming; Zhao Zanzan; Zhu Suhua; Xue Yuquan; Zhang Feng; (7 pag.)CN106317114; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 933721-91-6, Imidazo[1,2-a]pyridin-8-ylmethanamine, 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

A solution of compound 5e (60 mg, 0.15 mmol) and compound 19c (26 mg, 0.18 mmol) in ethanol (0.5 mL) was irradiated at 180 C. in a microwave instrument for two 30 min intervals, then concentrated. The residue was dissolved in methyl sulfoxide and purified by reversed-phase chromatography to furnish the title compound 188 as its trifluoroacetate salt. 1H NMR (methanol-d4): delta 8.66 (d, 1H, J=6.8 Hz), 8.20 (d, 1H, J=2.2 Hz), 8.01 (d, 1H, J=2.2 Hz), 7.46 (d, 1H, J=7.4 Hz), 7.33 (d, 2H, J=8.6 Hz), 7.28 (t, 1H, J=7.0 Hz), 7.15 (d, 2H, J=8.6 Hz), 6.88 (d, 2H, J=8.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 5.15 (s, 2H), 4.96 (s, 2H), 4.88 (s, 2H), 3.78 (s, 3H), 3.75 (s, 3H); HRMS m/z (M+H)+ calcd for C27H27N6O4 499.2094, found 499.2052.

The synthetic route of 933721-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Flores, Christopher M.; Wade, Paul R.; US2011/319400; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem