Category: pyridine-derivatives

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. 1044872-40-3, name is Methyl 2-amino-4,6-dichloronicotinate. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 116-3 The compound (2.2 g) obtained in step 116-2 and 2-propanol (31 ml) were mixed, and N,N-dimethylformamide dimethyl acetal (2.9 ml) was added. The mixture was heated under reflux for 30 min. The reaction mixture was cooled to room temperature, hydroxylamine hydrochloride (1.4 g) was added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated to an about half amount, and water (40 ml) and 2-propanol (6.6 ml) were added. The mixture was stirred at room temperature for 30 min, and the resulting solid was collected by filtration to give the compound described in the above-mentioned scheme (2.2 g, 84%).1H-NMR (DMSO-D6) delta: 3.92 (s, 3H), 7.37 (s, 1H), 7.85 (d, 1H, J=9.5 Hz), 10.12 (d, 1H, J=9.5 Hz), 10.83 (s, 1H).

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, 1044872-40-3, Methyl 2-amino-4,6-dichloronicotinate.

Reference:
Patent; JAPAN TOBACCO INC.; US2011/77267; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156072-84-3, 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. 156072-84-3, name is 5-Chloro-2-cyano-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH 5. ON (110 ml, 550 mmol). The resulting mixture was refluxed at 90 C for 18 h. After cooling to RT, the reaction mixture was conentrated, diluted with water and the pH of the solution was adjusted to 4 by addition of 5N HC1. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2X). The aqueous layer was again acidified with 5N HC1 to pH 4 and extracted with EtOAc (2X). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C for 12 h to give the title compound 5-chloro-3-methylpicolinic acid (24.1 g, 140 mmol, 89 % yield). LC/MS (ESf ) m/z = 172.0 (M+H)+; H NMR (400 MHz, CHLOROFORM -J) delta ppm 11.29 (br. s., 1 H), 8.41 (d, J=1.76 Hz, 1 H), 7.73 (d, J=1.76 Hz, 1 H), 2.75 (s, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 851386-40-8, 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.851386-40-8, name is 4-Chloro-2,5-difluoropyridine, molecular formula is C5H2ClF2N, molecular weight is 149.53, as common compound, the synthetic route is as follows.

To a microwave vial containing solution of 4-chloro-2,5-difluoropyridine (0.40 g, 2.7 mmol) in dioxane (7 mL), were added Intermediate 14C (1100 mg, 3.2 mmol), K3PO4 (1.30 g, 6.2 mmol), water (1.4 mL) and PdCl2(dppf)CH2Cl2 adduct (0.17 g, 0.21 mmol) at rt. The mixture was purged with nitrogen, and then was heated in a microwave reactor at 120 C for 6 min. The reaction mixture was cooled to rt. The aqueous layer was removed with a pipette. The organic phase was concentrated and was purified by normal phase chromatography to afford Intermediate 14D (350 mg, 47%) as a tan solid. LC-MS (ESI) m/z: 278.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 851386-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUAN, Mimi L.; HU, Zilun; WANG, Cailan; PATIL, Sharanabasappa; WO2015/2915; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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.

NaH (570 mg, 14.24 mmol) was added portion wise to stirred anhydrous DMSO (10 ml_). The mixture was heated to 80C until evolution of gas ceased and then cooled to 0C. A solution of (carbethoxymethyl)- triphenylphosphonium bromide (3.05 g, 7.12 mmol) in DMSO (10 ml_) was then added and the mixture stirred at r.t for 30 min. The mixture was cooled to 0C and a solution of 5-chloronicotinaldehyde (1 .0 g, 7.12 mmol) in DMSO (10 ml_) was added and the mixture was stirred at r.t for 1 h. The mixture was then poured into aqueous 1 M HCI and extracted into DCM (3 x 50 ml_). The organics were combined and washed with H2O (3 x 100 ml_) and brine (3 x 100 ml_), separated, dried (MgSO ) and concentrated. Purification by flash silica column chromatography (gradient elution /’-hex to 25% EtOAc in /-hex) gave the title compound as a yellow solid (1 .1 g, 57%). LCMS (ES+) 271 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; LUCKHURST, Christopher A.; HAUGHAN, Alan F.; BRECCIA, Perla; STOTT, Andrew J.; BURLI, Roland W.; HUGHES, Samantha J.; MUNOZ-SANJUAN, Ignacio; DOMINGUEZ, Celia; MANGETTE, John E.; WO2012/103008; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Example 12N-[6-(1 H-lndol-4-yl)-1 H-indazol-4-yl]pyrazolo[1 ,5-a]pyridine-2-carboxamide Pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (27 mg, 0.166 mmol) was treated with anhydrous THF (2ml) and then 1-chloro-N, N, 2-trimethylpropenylamine (0.026 ml, 0.20 mmol). The reaction was stirred at room temperature under nitrogen for 2 hrs. The reaction was then treated with anhydrous DIPEA (0.131 ml, 0.753 mmol) and 2ml of solution of 6-(1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (750mg, 2.26 mmol) in THF (30ml). The reaction was then stirred at room temperature under nitrogen for 69 hrs. The solvent was blown -off under a stream of nitrogen, dissolved in methanol (3ml) and then solvent removed under reduced pressure. The crude reaction mixture was dissolved in methanol (5ml), treated with Macroporous Tosic Acid (4.45 mmol/g, 102 mg, 0.45 mmol), stirred at room temperature for 17 hrs and then treated with 0.88 ammonia (0.5 ml), stirred for 30 minutes and then filtered. The solvent was removed under reduced pressure and then the residue purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound. LCMS (Method B) m/z 393 [MH+], R1 = 1.02min.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147189; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 697739-12-1, 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.697739-12-1, name is Ethyl imidazo[1,5-a]pyridine-8-carboxylate, molecular formula is C10H10N2O2, molecular weight is 190.2, as common compound, the synthetic route is as follows.

Ethyl imidazo [1, 5-a] pyridine-8-carboxylate (J. Het. CLIEIIZ., 1993,473) (0.21 g) was dissolved in 1M KOH in methanol (5 ml) and the solution heated at reflux for 5 min. The mixture was then concentrated, diluted with water (2 ml) and acidified to pH 1 with 2N HCI. The resulting precipitate was collected by filtration to give imidazo [1, 5-a] pyridine-8-carboxylic acid (80 mg) as a yellow solid.

Statistics shows that 697739-12-1 is playing an increasingly important role. we look forward to future research findings about Ethyl imidazo[1,5-a]pyridine-8-carboxylate.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/28445; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 117873-72-0, 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. 117873-72-0, name is 2,6-Dibromo-4-methoxypyridine, molecular formula is C6H5Br2NO, 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.

(1) Production of 2-bromo-4-methoxy-6-{3-(trifluoromethoxy)phenoxy} pyridine as an intermediate product 2.00 g (0.00937*1.2 mol) of 3-(trifluoromethoxy) phenol was dissolved in about 20 ml of dimethyl formamide. The solution was further mixed with 0.39 g (ca. 60% in mineral oil; 0.00937*1.04 mol) of sodium hydride and then with 2.50 g (0.00937 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 110 C. for about 4 hours, the mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed with hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane), and the obtained product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield by weight: 1.40 g; yield by percentage: 41%; oily substance; 1 H-NMR (60 MHz, CDCl3, delta): 3.73 (3H, s), 6.25 (1H, d, J=2 Hz), 6.69 (1H, d, J=2 Hz), 6.7-7.5 (4H, complex).

According to the analysis of related databases, 117873-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6005112; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1849-52-1, 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 1849-52-1, name is 3-Methoxyisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Compound VI (23.8 g, 0.1 mol) was added to a 500 mL three-necked flask. Add tetrahydrofuran (100 mL), The stirring was started, and tetramethylpiperidine lithium (LTMP) (44 mL, 0.11 mol) was added dropwise at -40 ° C under nitrogen atmosphere. After the addition is completed, continue to stir for 0.5 hours. Then, a solution of 3-methoxy-4-pyridinecarboxaldehyde (13.7 g, 0.1 mol) in tetrahydrofuran was added dropwise. After the drop, continue to react at -40 ° C for 1 hour, TLC point plate monitoring,After the material point disappears, a saturated ammonium chloride solution is added dropwise below zero, and ethyl acetate is added. Extract, separate the organic layer, add anhydrous sodium sulfate to dry, filter,The filtrate was concentrated under reduced pressure.Obtained a yellow solid compound V-1, 32.9 g,The yield was 88percent.

According to the analysis of related databases, 1849-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Jin Yanjuan; (11 pag.)CN108689998; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 942473-59-8, 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. 942473-59-8, name is 2,5-Dibromoisonicotinic acid, molecular formula is C6H3Br2NO2, 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.

EXAMPLE 1; ethyl 2,5-dibromoisonicotinate (1-2)A solution of 2,5-dibromoisonicotinic acid (KL, 5 g, 17.80 mmol) and sulfuric acid (1.23 mL, 23.1 mmol)in ethanol (100 mL) was heated to reflux overnight. After reducing the volume of ethanol by rotary evaporation to approximately 1A of it’s original volume, the crude reaction mixture was partitioned between 2M sodium carbonate solution and EtOAc, separating layers and washing the organic layer with saturated sodium bicarbonate solution and brine. This solution was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase column chromatography (O to 50% EtOAc in hexanes) to afford the product (I1T) as a dark oil. ESI+ MS [M]+ C8H7Br2NO2 = 308.0.

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 942473-59-8, 2,5-Dibromoisonicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BERGMAN, Jeffrey, M.; COLEMAN, Paul, J.; MATTERN, Mamio Christa; MERCER, Swati, P.; REGER, Thomas, S.; ROECKER, Anthony, J.; WO2010/51236; (2010); 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. 1032943-43-3, name is 4-Bromo-1H-pyrazolo[3,4-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Bromo-1H-pyrazolo[3,4-c]pyridine

4-Bromo- lH-pyrazolo[3 ,4-c]pyridine (2 g, 10.10 mmol) was dissolved in DCM (30 niL) and m-CPBA (2.61 g, 15.15 mmol) was added at 0 C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, solid precipitate was filtered and dried to afford 4-bromo-6-oxido-lH-pyrazolo[3,4-c]pyridin-6-ium (I, 2 g, 9.34 mmol, 92 52% yield). LCMS (ES +): m/z 215 [M + l l j

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, 1032943-43-3, 4-Bromo-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; HENDERSON, James, A.; VORA, Harit, U.; VEITS, Gesine, Kerstin; PHILIPS, Andrew, J.; (576 pag.)WO2020/51235; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem