Month: April 2022

Related Products of 1003-56-1 ,Some common heterocyclic compound, 1003-56-1, molecular formula is C6H7NO, 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 5: 1-(4-chlorobutyl)-3-methyl-2(1H)-pyridinone (Prep5); To a solution of 3-methyl-2(1 H)-pyhdinone (commercial aldrich) (200 mg, 1.85 mmol), in dry DMF (5 mL), K2CO3 (0.51 g) and 1-bromo-3-chlorobutane (0.32 mL) were added and the resulting mixture was heated at 90 C for 5 hours After solvent elimination under reduced pressure, the residue was diluted with ethyl acetate and washed once with water and once with brine The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure The crude product was purified by silica gel chromatography eluting with cyclohexane/EtOAc 8 2 to give the title compound as colourless oil (0 24 g) MS (m/z): 200 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-56-1, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/113258; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 113209-90-8, 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. 113209-90-8, name is (4-Chloro-5-fluoropyridin-2-yl)methanol. A new synthetic method of this compound is introduced below.

(v) Substituting 2-hydroxymethyl-4-chloro-5-fluoropyridine (2.5 g) for 2-hydroxymethyl-3-fluoro-4-chloropyridine and using corresponding molar proportions of the other reagents in the method of Example 27(v), gave 2-hydroxymethyl-4-morpholino-5-fluoropyridine (2.08 g) m.p. 134-136 (from acetonitrile).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113209-90-8, (4-Chloro-5-fluoropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline & French Laboratories Limited; US5250527; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22918-01-0, 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. 22918-01-0, name is 2-Bromo-4-chloropyridine. A new synthetic method of this compound is introduced below.

Example 103a 2-Bromo-4-chloronicotinaldehyde 103a To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70C was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C for another 1 h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL * 3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 103a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO) delta 10.21 (s, 1H), 8.52 (d, J= 5.5 Hz, 1H), 7.79 (d, J= 5.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22918-01-0, 2-Bromo-4-chloropyridine, 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

Reference of 623942-84-7, 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.623942-84-7, name is (3-Bromo-6-methoxypyridin-2-yl)methanol, molecular formula is C7H8BrNO2, molecular weight is 218.05, as common compound, the synthetic route is as follows.

(3-bromo-6-methoxypyridin-2-yl)methanol (2.5 g, 11.4 mmol) and CBr4 (4.5 g, 13.6 mmol) were added into DCM (30 mL). PPh3 (3.6 g, 13.6 mmol) in DCM (10 mL) was added dropwise into the reaction mixture at 0 C. The mixture was stirred at 0 C for 0.5 hour. The reaction was concentrated to give a residue. The residue was purified by flash silica gel chromatography (40 g column, EtOAc in petroleum ether from 0% to 10%) to afford 3- bromo-2-(bromomethyl)-6-methoxypyridine (2.69 g, 84% yield) as a colorless oil. LCMS m/z [M+H]+ = 281.8.

Statistics shows that 623942-84-7 is playing an increasingly important role. we look forward to future research findings about (3-Bromo-6-methoxypyridin-2-yl)methanol.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); 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. 24195-07-1, name is 2-(Methoxycarbonyl)nicotinic acid, the common compound, a new synthetic route is introduced below. Formula: C8H7NO4

methyl 3- [(fe^-butoxycarbonyl)aminolpyridine-2-carboxylate; To a mixture of 2- (methoxycarbonyi)nicotinic acid and 3-(methoxycarbonyl)pyridine-2-carboxylic acid (10.46 g, 57.7 mmol) is added tert-butanol (100 mL) and TEA (8.85 mL, 63.5 mmol). The reaction is stirred for five minutes at rt and then diphenyl phosphoryl azide (13.1 mL, 60.6 mmol) is added. The reaction is heated to reflux and stirred for approximately four hours. The reaction mixture is cooled to rt, concentrated to dryness, re-dissolved in EtOAc, and washed with water and saturated sodium bicarbonate (2 x 20 mL each). The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The mixture is purified by column chromatography (100% hexanes to 100% EtOAc) to yield the title compound and methyl 2-[(f°rt-butoxycarbonyl)amino]nicotinate (9.24 g, 64% yield). LCMS (ES, M+Na=275).

The synthetic route of 24195-07-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106326; (2006); 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. 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C12H9N3

Step 2: 8-Fluoro-4-((2-(pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)methyl)quinolin-2(1H)-one Sodium hydride (60% in mineral oil, 117 mg, 2.9 mmol) was added to 2-(pyridin-3-yl)-1H-benzo[d]imidazole (191 mg, 0.98 mmol) in DMF (5 mL) and stirred at RT for 15 min. 4-(Bromomethyl)-8-fluoroquinolin-2(1H)-one (300 mg, 1.2 mmol) was then added as a solid and the resulting mixture was stirred at RT for 18 h. The crude mixture was purified by preparative HPLC (ACN/water) to yield 60 mg (16%) of 8-fluoro-4-((2-(pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)methyl)quinolin-2(1H)-one as a pale yellow. 1H NMR (400 MHz, DMSO-d6, TFA salt) delta 11.86 (s, 1H), 8.93 (s, 1H), 8.72 (d, 1H), 8.13 (d, 1H), 7.86 (d, 1H), 7.69 (d, 1H), 7.64 (d, 1H), 7.59-7.57 (m, 2H), 7.40-7.36 (m, 2H), 7.26 (m, 1H), 5.94 (s, 2H), 5.53 (s, 1H). LCMS: 371 (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, 1137-67-3, 2-(Pyridin-3-yl)-1H-benzo[d]imidazole.

Reference:
Patent; KALYPSYS, INC.; US2008/139558; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.700811-29-6, name is 2-Chloro-4-hydrazinopyridine, molecular formula is C5H6ClN3, molecular weight is 143.5742, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-4-hydrazinopyridine

5.25 g (13.3 mmol) of (7), 3.78 g (17.5 mmol) of (2-Chloro-pyridin-4-yl)-hydrazine and 13.3 ml (74.7 mmol) of DIEA were suspended in 26.6 ml of NMP. The reaction mixture was capped and heated to 220 degrees C. via microwave irradiation. After 6 min., the reaction mixture was allowed to cool to RT. The reaction mixture was then poured onto a saturated aqueous solution of sodium bicarbonate. This aqueous phase was diluted with EtOAc and the layers were separated. The organic was dried over MgSO4, filtered and evaporated to dryness. This crude material was chromatographed on 6 inches of silica gel and eluted with 5-9% MeOH/CH2Cl2. The still slightly crude material was recrystallized from EtOAc/Hexane. Yield: 1.38 g, approximately 23%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,700811-29-6, 2-Chloro-4-hydrazinopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Salituro, Francesco; Ledeboer, Mark; Ledford, Brian; Wang, Jian; Pierce, Albert; Duffy, John; Messersmith, David; US2006/63756; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98353-08-3, 5-Ethoxypicolinic acid, 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, Safety of 5-Ethoxypicolinic acid, blongs to pyridine-derivatives compound. Safety of 5-Ethoxypicolinic acid

5-ethoxypicolinic acid (80mg, 0.479 mmol) was slurried in N,N-Dimethylformamide (dry) (2 ml), DIPEA (0.100 ml, 0.574 mmol) was added followed by HATU (200 mg, 0.526 mmol). After 15 mins 2-chloroaniline (0.056 ml, 0.526 mmol) was added to the brown suspension and the resulting reaction mixture stirred at room temperature for 20 hours. The reaction mixture was evaporated to dryness. This mixture was added to a cold water/ sat. sodium bicarbonate mixture (2:1, 20 ml) and DCM 20 mL. The product was extracted and the layers were separated over a phase separator. The filtrate was evaporated to dryness to give the product as a brown oil which solidified on standing. The product was purified further by reveleris 12 gram column using heptane-EtOAc gradient (0 to 25%) to afford a white solid. Used as such.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98353-08-3, 5-Ethoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; FORSCHUNGSVERBUND BERLIN E.V.; UNIVERSITY OF OULU; KRAUSS, Stefan; NAZARE, Marc; ANUMALA, Upendra Rao; LEHTIO, Lari; WAALER, Jo; HOLSWORTH, Dan; WEGERT, Anita; LEENDERS, Ruben Gerardus George; (99 pag.)WO2018/118868; (2018); 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. 116026-95-0, name is tert-Butyl (4-formylpyridin-3-yl)carbamate, the common compound, a new synthetic route is introduced below. Application In Synthesis of tert-Butyl (4-formylpyridin-3-yl)carbamate

Sodium triacetoxyborohydride (0.57 g, 2.70 mmol) and acetic acid (0.41, 6.75 mmol) were added to a solution OF N-BOC-3-AMINO-4-PYRIDINE carboxaldehyde (0.50 g, 2.25 mmol) and ETHYL 4-AMINOPIPERIDINE-1-CARBOXYLATE (0.47 g, 2.70 mmol) in dichloroethane (5 rriL) at room temperature. The reaction was stirred overnight, and quenched with saturated aqueous sodium bicarbonate. This was separated, extracted with ethyl acetate and the combined organics were dried over sodium sulfate. The solution was filtered and evaporated to give the crude product. This was purified by chromatography (silica GEL, 1 to 12% methanol in methylene chloride gradient elution), which gave the title compound (0.47 g). MS 379.3.

The synthetic route of 116026-95-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/92166; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100202-78-6, 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 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The commercially available starting material 1 (1.0mmol) was suspended in acetonitrile (10mL) containing K2CO3 (2.0mmol). The reaction was treated with an appropriately substituted arylalkyl derivatives 2a-o and 4a-4h (1.2mmol) and heated under reflux for 8h. The reaction progress was monitored using silica gel TLC with DCM/MeOH as mobile phase. Upon completion, the acetonitrile was evaporated in vacuo and the mixture was then poured into water, which was extracted with DCM, washed with brine, dried over anhydrous Na2SO4 and purified by chromatography (DCM/MeOH) on silica gel to afford the target compounds.

According to the analysis of related databases, 100202-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Zhi-Min; Cai, Pei; Liu, Qiao-Hong; Xu, Ding-Qiao; Yang, Xue-Lian; Wu, Jia-Jia; Kong, Ling-Yi; Wang, Xiao-Bing; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 282 – 297;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem