Pyridine-derivatives

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.18368-71-3, name is 4-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.COA of Formula: C6H6N2O2

Method 31; 3-Nitroisonicotinaldehyde 4-Methyl-nitropyridine (1.43g, 10.36mmol) was dissolved in dry DMF (5mL) and dimethylformamide dimethyl acetal (2. 0g, 16. 8mmol) was added. The mixture was heated under nitrogen at 140C for 2 hours and then evaporated under reduced pressure to give (E)- N, dimethyl-2-(3-nitropyridin-4-yl)ethyleneamine as a dark red solid. This was added in one portion at ambient temperature to a stirred solution of sodium periodate (6. 61g, 31mmol) in THF/ 1 1:1 (100mL). After stirring for 2hr at ambient temperature the reaction mixture was filtered and the solid washed with ethyl acetate (100mL). The washings were combined with the filtrate and organic layer separated. The aqueous was extracted with ethyl acetate (2 x lOOmL) and the combined organic layers were washed with saturated aqueous sodium bicarbonate (lOOmL) and brine (lOOmL), dried (MgS04) and evaporated under reduced pressure to give a brown solid which was purified by column chromatography (DCM) to give the title compound. (960mg, 61%). 1HNMR 7. 8 (d, 1H) ; 9. 15 (d, 1H) ; 9. 4 (s, 1H) ; 10. 4 (s, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-71-3, 4-Methyl-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2003/74532; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 79456-33-0, 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. 79456-33-0, name is 5-Chloro-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, 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 B ethyl 6-chloro-8-(trifluoromethyl)imidazo[l,2-a]pyridine-2-carboxylate[0121] 5-chloro-3-(trifluoromethyl)-2-pyridinamine (3.0 g, 15 mmol) and ethyl bromopyruvate (4.27 mL, 30.5 mmol) in N,N-dimethylformamide (50 mL) were stirred at 60 0C for 3 hours. The mixture was allowed to cool and then poured into stirring iced water. The precipitate was stirred for 5 minutes, collected by filtration, washed with water, and dried under vacuum to give the title compound (3.5 g; 78%). LCMS: m/z 293, 295 (M+l).

According to the analysis of related databases, 79456-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; BASKARAN, Subramanian; CATALANO, John; CHONG, Pek; DICKSON, Hamilton; FANG, Jing; MAUNG, Jack; NEITZEL, Martin, Leon; PEAT, Andy; PRICE, Daniel; RAI, Roopa; ROBERTS, Christopher, Don; SHOTWELL, Brad; TAI, Vincent; ZHANG, Huichang; WO2010/91411; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 82523-07-7, 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.82523-07-7, name is Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate, molecular formula is C8H7N3O2, molecular weight is 177.16, as common compound, the synthetic route is as follows.

Methyl 3H-imidazo[4,5-c]pyridin-6-carboxylate (44 mg, 0.25 mmol) was dissolved in N,N-dimethylformamide (2 mL) to which potassium carbonate (69 mg, 0.50 mmol) was added and then stirred at room temperature for 10 minutes. Then, benzyl (2R,3S)-2-(3-bromo-2-oxopropyl)-3-(tert-butyldimethylsilyloxy)piperidin-1-carboxylate (120 mg, 0.25 mmol) was added thereto and stirred at room temperature for 3 hours. When the reaction is completed, the solvent was removed, and the resulting mixture was diluted with ethyl acetate and then washed with saturated sodium chloride solution. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated under reduced pressure, and then purified by column chromatography (dichloromethane:methanol=10:1), thereby obtaining the title compound (110 mg, yield: 79%).

The chemical industry reduces the impact on the environment during synthesis 82523-07-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daewoong Pharmaceutical., Ltd.; Park, Joon Seok; Yoon, Youn Jung; Cho, Min Jae; Lee, Ho Bin; Yoo, Ja Kyung; Bong, Yong Lee; (47 pag.)US2017/88551; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 202217-19-4, 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.202217-19-4, name is 6-Chloro-5-methyl-3-nitropyridin-2-amine, molecular formula is C6H6ClN3O2, molecular weight is 187.58, as common compound, the synthetic route is as follows.

(2f) 5-Methyl-3-nitro-6-(2,2,2-trifluoroethoxy)-2- pyridinamine [Formula 23]; 2,2,2-Trifluoroethanol (340 mg, 3.4 mmol) was dissolved in the tetrahydrofuran (10 ml), sodium hydride (60%) (120 mg, 3.0 mmol) was added thereto, and the reaction mixture was stirred for 30 minutes at room temperature under nitrogen atmosphere. A solution of 6-chloro-5-methyl-3-nitro-2-pyridineamine crude product (400 mg) in tetrahydrofuran (10 ml) was dropped, and the reaction mixture was stirred at room temperature for 2.5 days. Water was added to the’ reaction solution and extracted with ethyl acetate, and after washed with a sodium bicarbonate solution, dried over magnesium sulfate. The residue obtained by evaporating the solvent was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n- hexane= 15/85) to yield the title compound (225 mg, 0.90 mmol) as a yellow solid. (at)H NMR (400MHz, DMSO-d6) No. ppm; 2.07 (3H, s), 5.06 (2H, J=9Hz), 8.05 (2H, s), 8.24(1H, s).

The chemical industry reduces the impact on the environment during synthesis 202217-19-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EISAI CO., LTD.; WO2005/103049; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131747-41-6, 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 131747-41-6 as follows.

To a mixture of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.0 equiv.) and 3-(trifluoromethyl)benzoic acid (1.1 equiv.) in DMF (0.27 M) was added HOAt (1.3 equiv.) and EDC (1.3 equiv.) After 3 h the reaction mixture was diluted with water and then extracted with EtOAc. The organic phase was washed sequentially with 1 M aqueous sodium hydroxide and brine and was then dried over sodium sulfate. The solution was concentrated and dried under vacuo to give N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(trifluoromethyl)pisonicotinamide in 91% yield. LCMS (m/z) (M+H)=407.1, Rt=1.13 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,131747-41-6, its application will become more common.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); 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. 108118-69-0, name is 2,6-Difluoropyridin-3-amine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a stirred solution of 1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-6]pyridine-5-carboxylic acid (47 mg, 0.17 mmol) in CH2C12 (2 mL) was added l-chloro-N,N-2-trimethylpropenylamine (45 muL, 0.34 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6-difiuoro- pyridin-3-ylamine (20 mg, 0.15 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue, to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150 ºC for 10 min, after which the resulting mixture was filtered and concentrated, affording 5- fluoro-2-[ 1 -(4-methoxy-benzyl)-1H-pyrroIo[2,3-b]rhoyridin-5-yl]-oxazolo[5,4-^]pyridine as a crude residue which was subsequently used without further purification. ES MS (M+H+) = 375.

The synthetic route of 108118-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/155017; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 627501-18-2, 5-Chloro-6-hydroxynicotinaldehyde, 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, Application In Synthesis of 5-Chloro-6-hydroxynicotinaldehyde, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Chloro-6-hydroxynicotinaldehyde

General procedure: Unless otherwise stated, the procedure was as follows. To a 1-dram (4 mL) vial equipped with a magnetic stir bar were added Pd(OAc)2 (4.4 mg, 0.02 mmol), alkene (0.2 mmol), acetic acid (6.0 mg, 0.1 mmol), nucleophile (0.3 mmol), and MeCN (0.1 mL). The vial was sealed with an unpunctured TFE septum-covered screw cap, and placed in a heating block that was pre-heated to 120 C. After the designated reaction time, the dark black reaction was purified either by flash column chromatography only or by flash column chromatography followed by an aqueous workup to produce the desired product.

The synthetic route of 627501-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gurak, John A.; Tran, Van T.; Sroda, Miranda M.; Engle, Keary M.; Tetrahedron; vol. 73; 26; (2017); p. 3636 – 3642;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52538-09-7 , The common heterocyclic compound, 52538-09-7, name is 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine, molecular formula is C8H9N3, 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 K 3-Methyl-3H-imidazo[4,5-c]pyridine-2-carboxaldehyde Employing the procedure of Example 10B and starting with 774 mg of 2,3-dimethyl-3H-imidazo[4,5-c]pyridine (Preparation J2) and 584 mg of selenium dioxide in 30 ml of dioxane, there was obtained 442 mg of the desired product.

The synthetic route of 52538-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4782050; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-83-6 ,Some common heterocyclic compound, 69045-83-6, molecular formula is C6H2Cl5N, 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 7 This Example illustrates the preparation of 2,3-dichloro-5-trifluoromethylpyridine by fluorination of 2,3-dichloro-5-trichloromethylpyridine, using a fluorinating agent alternative to that of Example 6. 2,3-Dichloro-5-trichloromethylpyridine (35 g) was heated with anhydrous hydrogen fluoride (100 g) in an autoclave at 200 for 10 hours with stirring. The cooled reaction mixture was poured on to ice and neutralised with sodium hydroxide at 0. The mixture was extracted with methylene chloride (750 ml). The extracts were washed with water (500 ml), sodium carbonate solution (500 ml) and water (500 ml), dried, and evaporated. The remaining oil was distilled and the fraction of boiling point 77-83/25 Torr was collected and identified as the required pyridine derivative.

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. 69045-83-6, 2,3-Dichloro-5-(trichloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries Limited; US4317913; (1982); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89978-52-9, 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 89978-52-9, name is Ethyl 2-bromoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

4-cyano-2-naphthaleneboronic acid (0.10 g), 2-bromoisonicotinic acid ethyl ester (0.12 g) and cesium fluoride (0.09 g) in dimethoxyethane (6 mL) was added tetrakis (triphenylphosphine) palladium (0.06 g), and the mixture was stirred at 150C for 40 minutes using microwave reactor (Biotage). The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 2-(4-cyanonaphthalene-2-yl) isonicotinic acid ethyl ester (0.14 g). To a solution of this compound (0.14 g) in a mixed solvent of tetrahydrofuran (4 mL), ethanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.060 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added acetic acid (0.27 mL). The precipitated solid was collected by filtration, and washed with water and n-hexane. The solid was dried under reduced pressure to give the title compound (0.098g).

According to the analysis of related databases, 89978-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; SHIMIZU, Kazuo; IIZUKA, Masato; FUJIKURA, Hideki; TAKIGAWA, Yasushi; HIRATOCHI, Masahiro; EP2343279; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem