Month: April 2022

Synthetic Route of 884494-51-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid, molecular formula is C6H3FINO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1 : Methyl 2-(((3R.6R)-l-(ter?-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4- iodonicotinate A solution of 2-fluoro-4-iodonicotinic acid (4.43 g, 16.61 mmol) in DMSO (75 ml) was treated with sodium hydride (0.471 g, 19.62 mmol) in portions. After stirring a few minutes, (2R,5R)-tert-butyl 5-hydroxy-2-methylpiperidine-l-carboxylate (8, 3.25 g, 15.10 mmol) was added. Additional sodium hydride (0.362 g, 15.10 mmol) was added in portions and, after stirring for a few minutes, the reaction was heated at 40 C for 2 days. The reaction was cooled and quenched with saturated, aqu. NH4C1, then rapidly diluted with H2O and EtOAc. Cone. HCl was added until the the solution was acidic, then rapidly extracted 3x with EtOAc. The organics were washed 2x with H20, lx with brine, dried over MgS04, filtered, concentrated, and dried to provide the crude carboxylic acid. The crude foam was dissolved in DMF (76 mL) and cooled at 0 C and treated with sodium hydride (0.55 g, 23 mmol) in portions. After stirring ~10 mins, iodomethane (1.34 mL, 21.4 mmol) was added and the reaction was warmed to RT overnight. The reaction was cooled at 0 C and quenched by additon of saturated, aqu. NH4C1 and stirred well. Saturated, aqu. aHC03 was added and the reaction was extracted 2x with EtOAc. The organic fractions were washed with brine, dried over MgS04, filtered, and concentrated to provide the title compound as a crude oil. LRMS m/z (M+H) 477.3 found, 477.1 required.

According to the analysis of related databases, 884494-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/62533; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 42373-30-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 42373-30-8, name is 4-Aminonicotinaldehyde, molecular formula is C6H6N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 4: A solution of 4-aminonicotinaldehyde (57 mg, 0.47 mmol) in tetrahydrofuran was cooled in an ice bath and lithium aluminium hydride (27 mg, 0.70 mmol, 1.5 eq) was added. The ice bath was removed and the reaction mixture was sittred for 30 min. TLC showed complete consumption of starting material. The reaction mixture was quenched with water (1 mL) and 1 N HCl (2 mL) was added extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was used for the next reaction with in a crude state (60 mg, 99%).

According to the analysis of related databases, 42373-30-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/29961; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 688782-02-7, 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. 688782-02-7, name is 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

To a mixture of 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine (0.20 g, 1.20 mmol), Pd(OAc)2 (0.013 g, 0.060 mmol) and Xantphos (0.069 g, 0.12 mmol) in dioxane (3.0 mL, 1.200 mmol) under Ar gas was added methyl 3-mercaptopropanoate (0.15 mL, 1.32 mmol) and Hunig’s base (0.42 mL, 2.4 mmol). The reaction was heated to 150C under argon in a microwave reactor for 2 hours. 3-mercaptopropanoate (0.15 mL, 1.32 mmol) was added and heated to 200C in the microwave reactor for 2 hours. The reaction mixture was cooled and diluted with EtOAc (25 mL) and filtered through celite. The filtrate was concentrated and the resulting residue was purified by flash chromatography with a 0 to 10% MeOH in EtOAc gradient. The material was subjected to a DCM trituration to afford methyl 3-((3-methyl-1H- pyrrolo[2,3-b]pyridin-4-yl)thio)propanoate (0.042 g, 0.17 mmol, 14 % yield). m/z (esi/APCI) M+1 = 251.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,688782-02-7, 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; BOYS, Mark Laurence; CHICARELLI, Mark Joseph; COOK, Adam; ELSAYED, Mohamed S. A.; FELL, Jay B.; FISCHER, John P.; HINKLIN, Ronald Jay; MCNULTY, Oren T.; MEJIA, Macedonio J.; RODRIGUEZ, Martha E.; WONG, Christina E.; (259 pag.)WO2020/81848; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54401-85-3 ,Some common heterocyclic compound, 54401-85-3, molecular formula is C9H11NO2, 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.

A. 4-Pyridineethanol Fifteen grams (0.091 mol) of 4-pyridineacetic acid ethyl ester was dissolved in 180 ml of dry THF. The solution was transferred to a 1 l., 3-neck round bottom flask which had been flushed with nitrogen. To the mixture was added dropwise 55 ml of 1.0 M lithium aluminum hydride (0.055 mol) at approximately 0 C. The reaction mixture became yellow upon addition of the reducing agent. Following addition, the mixture was quenched with 2.1 ml of water at 0 C. followed by 2.1 ml of 15% by volume of sodium hydroxide and 6.3 ml of water. The mixture was allowed to stir at room temperature for approximately 4 hours and filtered through Celite. The filtrate was concentrated under vacuum to provide 6.38 g of 4-pyridineethanol. This material was used directly in the following reaction.

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. 54401-85-3, Ethyl 4-pyridylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; US4968678; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1233205-73-6, 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.1233205-73-6, name is 2-Ethynyl-6-fluoropyridine, molecular formula is C7H4FN, molecular weight is 121.11, as common compound, the synthetic route is as follows.

To a solution of the compound obtained in the previous section (1.45 g, 4.54 mmol) and the reference example 2 (0.50 g, 4.13 mmol) in AcN (20 ml_ ) at 0 5C, a DBU (1.24 ml_, 8.26 mmol) solution in AcN (7 ml_) was slowly added. The resulting mixture was heated at 50 0C for 18 h. After that, was cooled and concentrated to dryness. The crude product obtained was chromatographed over silica gel using hexane/EtOAc mixtures of increasing polarity as eluent, to afford 0,48 g of the desired compound (45% yield). LC-MS (Method 2): tR = 3.03 min; m/z = 239 (MH+).

Statistics shows that 1233205-73-6 is playing an increasingly important role. we look forward to future research findings about 2-Ethynyl-6-fluoropyridine.

Reference:
Patent; PALAU PHARMA, S. A.; SALAS SOLANA, Jorge; ALMANSA ROSALES, Carmen; COMELLES ESPUGA, Josep; FONTES USTRELL, Montserrat; SOLIVA SOLIVA, Robert; PASTOR PORRAS, Jose, Javier; WO2010/72823; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98197-88-7, 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 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-(methoxymethyl)-4-nitropyridine (i59): To a solution of (4-nitropyridin-2-yl)methanol (i58) (2.3 g, 14.93 mmol) in THF (40 mL), NaH (0.89 g, 22.40 mmol) was added at 0C and stirred for 5 min. Mel (3.18 g, 22.4 mmol) was added and the reaction mixture allowed to warm to room temperature and stirred for 4h. The progress of the reaction was monitored by TLC. After completion, the mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by silica gel (60:120 mesh) column chromatography using 10% ethyl acetate in n-hexane as eluent to afford 2-(methoxymethyl)-4-nitropyridine (i59) (0.775 g, Yield 31 %). 1H NMR (400 MHz, DMSO-d6) delta 3.44 (s, 3H), 4.66 (s, 2H), 8.08 – 8.00 (m, 2H), 8.91 (d, J = 5.2 Hz, 1 H). MS (ESI) m/e (M+1 )+: 169.00

According to the analysis of related databases, 98197-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; PROVINS, Laurent; VERMEIREN, Celine; SABNIS, Yogesh Anil; (106 pag.)WO2016/124508; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183428-91-3, 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.183428-91-3, name is 2-Amino-3-methyl-5-cyanopyridine, molecular formula is C7H7N3, molecular weight is 133.15, as common compound, the synthetic route is as follows.

Step II: 6-Amino-5-methyl-pyridine-3-carboxylic acid To a stirred suspension of 6-amino-5-methyl-pyridine-3-carbonitrile (6.0 g, 45.0 mmol) in water (40 mL) was added sodium hydroxide (5.4 g, 135.2 mmol) and refluxed for 4 h. Reaction mixture was cooled to room temperature and filtered through Buchner funnel. Filtrate was neutralized with 4N HCl. Solid formed was filtered through Buchner funnel and dried under high vacuum to furnish 6.0 g (88%) of titled intermediate as a white solid. 1H NMR (400 MHz, CDCl3): delta 2.05 (s, 3H), 6.53 (s, 2H), 7.66 (s, 1H), 8.37 (d, J=2.0 Hz, 1H), 12.29 (brs, 1H). MS (ES) m/z 153.0 (M+1).

Statistics shows that 183428-91-3 is playing an increasingly important role. we look forward to future research findings about 2-Amino-3-methyl-5-cyanopyridine.

Reference:
Patent; Kharul, Rajendra; Bhuniya, Debnath; Mookhtiar, Kasim A.; Singh, Umesh; Hazare, Atul; Patil, Satish; Datrange, Laxmikant; Thakkar, Mahesh; US2015/65464; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 113713-60-3, 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 113713-60-3, name is 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 113713-60-3, 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine.

Reference:
Article; Gao, Mingzhang; Wang, Min; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 26; 5; (2016); p. 1371 – 1375;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 57963-08-3, 5,6-Dimethylpyridin-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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: A mixture of the arylhydrazine hydrochlorides (1.0 mmol), aminopyridines (20.0 mmol), and potassium carbonate (415 mg, 3.0 mmol) in DMSO (10 mL) was stirred at 25 C in air. The reactions were completed after 24 h, monitored by thin layer chromatography (TLC). Then, quenched by the addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine solution and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give the crude products. Purified by column chromatography over silica gel (hexane/AcOEt), the pure products were afforded.

The synthetic route of 57963-08-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Taniguchi, Toshihide; Imoto, Mitsutaka; Takeda, Motonori; Matsumoto, Fukashi; Nakai, Takeo; Mihara, Masatoshi; Mizuno, Takumi; Nomoto, Akihiro; Ogawa, Akiya; Tetrahedron; vol. 72; 27-28; (2016); p. 4132 – 4140;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1122-61-8, 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. 1122-61-8, name is 4-Nitropyridine. A new synthetic method of this compound is introduced below.

General procedure: A solution of complex 4a (1 g, 4.25 mmol) in benzene (10 ml) was stirred at 15-20 and treated with a solution of heterocyclic amine or oxaadamantane () (4.25 mmol) in benzene (5 ml) (Scheme 10, Table 1). The reaction mixture was stirred for the indicated time at room temperature, with periodic control of the amount of evolved THF by GLC (60-70, adsorbent – chromosorb, liquid phase – PEG monolaurate). After the increase of THF signal stopped, the reaction mixture was evaporated from Petri dish under exaust hood, the residue was extracted first with hexane and then with Et2O. The combined extract was evaporated under vacuum at room temperature, the residue was recrystallized from Et2O-hexane mixture. Complexes of trinitromethylborane with amines (compounds 7-s) or with oxaadamantanes (compounds 4d,e) were thus obtainecharacteristics, as well as yields and melting points of target complexes 4d,e and 7-s are given in Table 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-61-8, its application will become more common.

Reference:
Article; Shitov; Tartakovskii; Ioffe; Chemistry of Heterocyclic Compounds; vol. 50; 12; (2015); p. 1647 – 1657; Khim. Geterotsikl. Soedin.; vol. 50; 12; (2014); p. 1795 – 1806,12;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem