Day: April 11, 2022

Synthetic Route of 73112-16-0, Adding some certain compound to certain chemical reactions, such as: 73112-16-0, name is 2,6-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 73112-16-0.

[00170] A solution of n-BuLi (4.4 mL, 2.5 M in n-hexane, 11 mmol) was slowly added to a solution of 2,6-dibromo-4-methylpyridine (2.75 g, 10.9 mmol) in DCM (83 mL) at -78C under N2. After stirring for 1.5 hat -78 C, methyl 3- oxocyclopentanecarboxylate (1.54 g, 11.0 mmol) was added. The cooling bath was removed and the reaction mixture was stirred for 2 h, and then was quenched by addition of saturated aqueous NH4C1 solution. The reaction mixture was extracted with ethyl acetate, and the organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (isocratic elution, 8% ethyl acetate-petroleum ether) to give two product diastereomers. Peak 1(550 mg, yellow solid) was determined to be the 1R,3S and 1S,3R isomers, and peak 2 (350 mg, yellow oil) was determined to be the 1R,3R and 1S,3S isomers. MS (ES+) C13H16BrNO3 requires: 313, found: 314 [M+H].

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31170-78-2, 5H-Cyclopenta[b]pyridin-7(6H)-one, 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, Recommanded Product: 5H-Cyclopenta[b]pyridin-7(6H)-one, blongs to pyridine-derivatives compound. Recommanded Product: 5H-Cyclopenta[b]pyridin-7(6H)-one

5,6-Dihydro-[1]pyrindin-7-one O-methyl-oxime: Methoxylamine hydrochloride (6.20 g, 74.23 mmol) was added to a solution of 5,6-dihydro-[1]pyrindin-7-one (4.96 g, 37.25 mmol) in MeOH and triethylamine (10.4 mL, 74.62 mmol) was added. After refluxing overnight, the reaction mixture was cooled to room temperature and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with H2O (3×200 mL), brine (1×200 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hex: Et2O (4:1) as the eluant afforded 4.10 g (68% yield) of the title oxime.31 g (96.5% yield) of the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 2.90-2.96 (m, 2H), 2.99-3.07 (m, 2H), 4.08 (s, 3H), 7.21 (q, J=4.69, 2.93 Hz, 1H), 7.63 (d, J=7.92 Hz, 1H), 8.55 (d, J=4.69 Hz, 1H).

The synthetic route of 31170-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2008/255239; (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. 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde. A new synthetic method of this compound is introduced below., Formula: C8H6N2O

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

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, 130473-26-6, 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
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. 716362-10-6, name is 6-Chloro-4-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6ClNO3

Triethylamine (7.0 mL, 51 mmol) was added to a suspension of 6-chloro-4-methoxynicotinic acid (2.615 g, 13.94 mmol, Intermediate 66) in MeCN (93 mL). N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (3.74 g, 19.5 mmol), HOBt (2.64 g, 19.5 mmol), and N,O-dimethylhydroxylamine hydrochloride (2.05 g, 21.0 mmol) were added, and the resulting mixture was stirred at rt for 3 days. After this time, the mixture was concentrated, and the residue was dissolved in EtOAc and water. The layers were mixed and separated, and the aqueous layer was extracted five times with EtOAc. The organic layers were combined, dried with anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0?20% EtOAc/hexanes) to provide the title compound.

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, 716362-10-6, 6-Chloro-4-methoxynicotinic acid.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Kummer, David A.; Nishimura, Rachel T.; Fourie, Anne M.; Xue, Xiaohua; (94 pag.)US2019/382373; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 150054-50-5, 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.150054-50-5, name is (4-Chloro-3,5-dimethylpyridin-2-yl)methanol, molecular formula is C8H10ClNO, molecular weight is 171.62, as common compound, the synthetic route is as follows.

EXAMPLE 8 Synthesis 2-hydroxymethyl-4-Methoxy-3,5-Lutidine In a round bottom flask equipped with a stirrer, a condenser and a nitrogen bubbler, 4-Chloro-2-hydroxymethyl-3,5-Lutidine (1 eq.) was dissolved in Dimethylformamide (3-9 volumes) and Methanol (1.5-4.5 volumes). Sodium methoxide (4 eq.) was added and the temperature was raised to (95-100? C.). At the end of the reaction the solvent was distilled under vacuum. Water (2 volumes) was added to the residue and the product was extracted with dichloromethane (2*4 volumes). The combined organic extracts were dried over sodium sulfate, filtered and evaporated. The crude product, 2-hydroxymethyl-4-Methoxy-3,5-lutidine, was obtained in 55% yield. In another work-up method, after evaporation of the dimethylformamide/methanol, water (2 volumes was added to the residue and the product was extracted with toluene (3*4 volumes). The organic extracts were combined and while cooling and stirring HCl gas (1.2 eq.) was bubbled into solution. The product 2-hydroxymethyl-4-Methoxy-3,5-lutidine hydrochloride salt was filtered and washed with toluene. The crude product was obtained as a white solid in 50% yield.

The chemical industry reduces the impact on the environment during synthesis 150054-50-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PDi-Research Laboratories, Inc.; US6437139; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6622-91-9 ,Some common heterocyclic compound, 6622-91-9, molecular formula is C7H8ClNO2, 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.

Example 12 Synthesis of N-[(4-pyridyl)acetyl]-D,L-alanine iso-butyl ester Following General Procedure F and using 4-pyridylacetic acid hydrochloride (Aldrich) and (D,L)-alanine iso-butyl ester hydrochloride (from Example B above), the title compound was prepared as a solid having a melting point of 64-66C. The reaction was monitored by tlc on silica gel (Rf = 0.43 10% methanol/dichloromethane) and purification was by silica gel chromatography. NMR data was as follows: 1H-nmr (CDCl3): delta = 8.51 (dd, J = 1.6, 2.8, 1.6, 2H); 7.23 (dd, J = 4.3, 1.6, 4.4, 2H); 6.71 (d, J = 6.8, 1H); 4.56 (quint., J = 7.3, 7.2, 1H); 3.88 (m, 2H); 3.53 (s, 2H); 1.89 (m, 1H); 1.36 (d, J = 7.2, 3H); 0.88 (d, J = 6.7, 6H). 13C-nmr (CDCl3): delta = 173.5, 169.3, 150.5, 144.4, 125.1, 72.1, 48.9, 43.0, 28.2, 19.5, 19.5, 18.9. C14H20N2O3 (MW = 264, Mass Spectroscopy (MH+ 265)) GENERAL PROCEDURE ELow Temperature BOP Coupling of Acid and Alcohol A solution of methylene chloride containing the carboxylic acid (100M%) and N-methyl morpholine (150 M%) was cooled to -20C under nitrogen. BOP (105 M%) was added in one portion and the reaction mixture was maintained at -20C for 15 minutes. The corresponding alcohol (120 M%) was added and the reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was then poured into water and extracted with ethyl acetate (3x). The combined ethyl acetate portions were backwashed with saturated aqueous citric acid (2x), saturated aqueous sodium bicarbonate (2x), brine (1x), dried over anhydrous magnesium sulfate or sodium sulfate and the solvent removed under reduced pressure to yield the crude product

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. 6622-91-9, 2-(Pyridin-4-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Elan Pharmaceuticals, Inc.; ELI LILLY AND COMPANY; EP951464; (2005); B1;,
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. 856013-04-2, name is 6-Bromopyridine-2-sulfonamide. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H5BrN2O2S

6-Bromopyridine-2-sulphonamide (0.5 g, 2.11 mmol, prepared by the methods described in WO2005/058299) and potassium carbonate (2.92 g, 21.1 mmol) were initially charged in acetonitrile (10 ml). While cooling with ice, acetyl chloride (1.16 g, 14.8 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure, and the residue was taken up in water and acidified with dilute hydrochloric acid solution. It was extracted with ethyl acetate and the solvent was removed under reduced pressure. This gave 0.54 g (85% of theory) of N-[(6-bromopyridin-2-yl)sulphonyl]-acetamide.HPLC-MS: LogP(HCOOH): 0.95; mass (m/z): 278.9 (M+H)+;1H NMR (d6-DMSO): 1.99 (s, 3H), 7.99-8.01 (m, 1H), 8.08 (t, 1H), 8.11-8.13 (m, 1H), 12.48 (s, 1H) ppm.

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, 856013-04-2, 6-Bromopyridine-2-sulfonamide.

Reference:
Patent; BAYER CROPSCIENCE AG; US2012/165345; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38222-83-2, Adding some certain compound to certain chemical reactions, such as: 38222-83-2, name is 2,6-Di-Tert-butyl-4-methylpyridine,molecular formula is C14H23N, 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 38222-83-2.

4-Bromomethyl-2,6-di-t-butylpyridine (Compound A3) To a mixture of 2,6-di-t-butyl-4-methylpyridine (Aldrich, 2.0 g, 9.73 mmol) in 25 ml of dry CCl4 was added benzoyl peroxide (24 mg, 0.097 mmol) and NBS (1.9 g, 10.7 mmol). The reaction mixture was refluxed for 16 hours. After it cooled to room temperature, the solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, hexane) to give an oil (1.957 g) which contained 82% of the desired product and 18% of the starting material. 1 H NMR delta 7.09 (s, 2H), 4.39 (s, 2H), 1.35 (s, 18H).

According to the analysis of related databases, 38222-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan Sales, Inc.; US5965606; (1999); A;,
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. 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine. A new synthetic method of this compound is introduced below., Product Details of 131747-55-2

The above example 2-fluoropyridin-3-yl-methanol was dissolved in 85 mL of dichloromethane,Ice bath 10min,21.7 mL (306.04 mmol) of thionyl chloride was slowly added dropwise.The reaction solution changed from yellow to brown, and the reaction was continued for 2 hours.TLC monitoring, the reaction is complete, continue the ice bath for a while, slowly add 100mL of water, N2 blow, alkali absorption gas, dichloromethane (100mL*3) extraction, 100mL saturated brine, dry anhydrous MgSO4, vacuum distillation Solvent, 7.14g of brown liquid, ready for use

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, 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Li Song; Zheng Zhibing; Lin Feng; Gong Zehui; Lu Xinqiang; Zhou Xinbo; Zhong Wu; Xiao Junhai; Xie Yunde; Li Xingzhou; Wang Xiaokui; (16 pag.)CN107964018; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 91678-23-8, 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.91678-23-8, name is 2-Bromo-6-chloro-3-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

To a solution of 2-bromo-6-chloro-3-nitropyridine (3g, 12.63 mmol) in acetonitrile (60 ml_) was added butyl(1 -ethoxyvinyl)-l2-stannane compound with octane (4.56 g, 12.63 mmol), PdCl2(PPh3)2 (1 .330 g, 1 .895 mmol), and copper(l) iodide (0.120 g, 0.632 mmol) under nitrogen at room temperature. The reaction mixture was stirred at 60 C for 6h. The reaction was allowed to cool to room temperature and filtered with diatomite. The filter cake was washed with acetonitrile and the organic layers were combined. The resulting solution was concentrated under reduced pressure to afford the crude product. The crude product was purified by silica gel column chromatography, eluted with ethyl acetate/petroleum ether, and concentrated under reduced pressure to afford the title compound as a brown solid (2.8 g, 75% pure, 72.7% yield).

The chemical industry reduces the impact on the environment during synthesis 91678-23-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EVANS, Karen Anderson; HILFIKER, Mark A.; MARCUS, Andrew Peter; PLOTNIKOV, Nikolay Valeryevich; RALPH, Jeffrey Michael; (142 pag.)WO2019/193540; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem