Month: April 2022

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

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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5BrClN

[0415] To a stirred solution of sodium metal (4.46 g, 194 mmol) in MeOH (200 mL) under an argon atmosphere was added 3-bromo-2-chloro-6-methylpyridine (20 g, 97 mmol) at 0 C. The reaction mixture was stirred at 100 C for 4 h in a sealed tube. After consumption of starting material (by TLC), volatiles were evaporated in vacuo. The residue was quenched with water (200 mL) and extracted with EtOAc (2 x 250 mL). The combined organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to obtain 3-bromo-2- methoxy-6-methylpyridine (18 g, 92%) as colorless liquid.?H-NMR (CDC13, 400 MHz): 7.61 (d, 1H), 6.60 (d, 1H), 3.99 (s, 3H), 2.39 (s, 3H); LCMS:99.6%; 201.8 (M+1); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 jtm); RT 2.67 mm; mobile phase: 0.025% Aq TFA+5% ACN: ACN+5% 0.025% Aq TFA; T/B%: 0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 10% EtOAc/ Hexane (R1 0.7). Synthesis of 5-bromo-6-methoxypicolinic acid:

With the rapid development of chemical substances, we look forward to future research findings about 185017-72-5.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline, the common compound, a new synthetic route is introduced below. SDS of cas: 185017-72-5

a) 1-(2-Chloro-6-methylpyridin-3-yl)cyclobutanol A suspension of molecular sieves (4 A) and 3-bromo-2-chloro-6-methylpyridine (CAN 185017-72-5, 5 g, 24.2 mmol) in THF (50 mL) was cooled to -15 C. 1.3 M isopropyl magnesium chloride lithium chloride complex solution in THF (19.6 mL, 25.4 mmol) was added within 30 mm. Stuffing was continued for 1 h at -15 C. Cyclobutanone (1.87 g, 2.00 mL, 26.6 mmol) was slowly added. Stirring was continued for 2 h at -15 C and for further 2 h at 0 C. Water (2.5 mL) was added, the mixture was concentrated in vacuo, and poured onto sat. aqueous NH4C1 solution. The mixture was extracted with EtOAc (2 x 100 mL).The combined extracts were washed with ice water (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 140 g, heptane / EtOAc 0-40% in 120 mm.) to give the title compound (3.33 g, 70%) as white solid, MS (ESI): mle = 198.1 [MHi.

The synthetic route of 185017-72-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FREI, Beat; GOBBI, Luca; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/86705; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1314353-68-8, 5-Cyclopropylpyridin-3-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, Quality Control of 5-Cyclopropylpyridin-3-amine, blongs to pyridine-derivatives compound. Quality Control of 5-Cyclopropylpyridin-3-amine

At 0 C, to a solution of 5-cyclopropylpyridin-3-amine (2.08 g, 15.49 minol) in tetrahydrofuran (30 mL) was added a solution of NaHMDS (6.84 g, 37.30 minol) in tetrahydrofuran (20 mL) dropwise over 10 min period. The resulting solution was stirred for 1 h at 0 C, and then was added by a solution of di-tert-butyl dicarbonate (4.85 g, 22.20 minol) in tetrahydrofuran (25 mL) dropwise. The resultingminxture was stirred for additional 2 h at room temperature. When the reaction was done, it was quenched by the addition of sat. NH4C1 solution (100 mL). The resultingminxture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with MeOH in EtOAc (0% to 80% gradient) to yield tert-butyl N-(5- cyclopropylpyridin-3-yl)carbamate as white solid (2.52 g, 69%). MS: m/z = 235.0 [M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1314353-68-8, 5-Cyclopropylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; SHERER, Brian A.; BRUGGER, Nadia; (546 pag.)WO2017/106607; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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

4.48 g (20 mmol) of the compound obtained in the preceding step in solution in 100 ml of diethyl ether and 9.05 ml (60 mmol) of tetramethylethylene-diamine are placed in a reactor, protected from moisture, and under a nitrogen atmosphere. After having cooled the solution to -70 C., 37.5 ml (60 mmol) of n-butyllithium in hexane (1.6 M) are added dropwise.. The reaction medium is stirred for 2 hours at -10 C. and then 14.1 g (60 mmol) of dihexyl sulfide are added dropwise at -70 C. After stirring the solution for 12 hours at room temperature, the reaction medium is taken up in water and extracted with diethyl ether.. The organic phase is washed with hydrochloric acid (0.1 M) and then with water until a PH of the washings equal to 7 is obtained, and then finally dried over sodium sulfate.. After evaporation of the solvent, an oil is obtained which is chromatographed on a silica gel (eluent ethyl acetate-hexane: 1-5).. After evaporation of the solvent, 5.6 g of an oil is obtained which crystallizes, that is to say a yield of 82.3%.. Its melting point is between 72 and 74 C. TLC: (MERCK “Kieselgel 60” silica gel; AcOEt-hexane: 1-3); Rf=0.3 I.R.: upsilon NH=3171, CO=1720; NMR: (CDCl3): 0.85 (t, 3H); 1.3 (m, 4H); 1.45 (m, 11H); 1.7-1.8 (m, 2H); 3.0 (t, 2H); 4.25 (s, 3H); 6.7 (d, 1H, J=6.8 Hz); 7.85 (d, 1H, J=6.8 Hz).

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

Reference:
Patent; Merck Patent GmbH; US6339097; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem