Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 942920-55-0, Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, 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 Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of Ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

To a mixture ethyl 4-bromo-1 H-pyrrolo[2,3-b]pyridine-2-carboxylate (500 mgs, 1.86 mmol) and 2-((tetrahydro-2H-pyran-4-yl)oxy)-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzonitrile (673 mgs, 2.0 mmol) in DME (6 mL) was 2.0 M aqueous Na2CO3 (2.0 mL, 4 mmol) and Pd(PPh3)4 (107 mgs, 0.09 mmol). The reaction mixture was heated at 140 C for 1 hr. After cooling to rt, ethyl acetate (10 mL) and water (20 mL) was added and the solids were filtered and washed with water and dried to give ethyl 4-(3-cyano-4-((tetrahydro-2H-pyran-4-yl)oxy)phenyl)-1 H-pyrrolo[2,3- b]pyridine-2-carboxylate (500 mgs) LCMS-ESI+ (m/z): [M+H]+ calcd for C22H21 N3O4 as (M+H)+ 392.4 found: 392.1

The synthetic route of 942920-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; DU, Zhimin; GUERRERO, Juan, Arnaldo; KAPLAN, Joshua, Aaron; KNOX, JR., John Edward; NADUTHAMBI, Devan; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William, J.; ZABLOCKI, Jeff; WO2015/187684; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 107504-08-5, 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. 107504-08-5, name is 5-Fluoro-2-picolinic acid. A new synthetic method of this compound is introduced below.

Example B13Preparation of compound 24: (7?)-5-fluoro-pyridine-2-carboxylic acid [3-(4-amino-2- cyano-6-methyl-6,7-dihydro-pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amideN. F 5-Fluoro-2-pyridinecarboxylic acid (87.4 mg, 0.619 mmol) was added to a mixture of 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (171.3 mg, 0.619 mmol) in MeOH (3 mL). The mixture was stirred at room temperature for 30 min, then it was cooled to 0 C and a solution of intermediate A63 (160 mg,0.563 mmol) in MeOH (3 mL) was added. The mixture was warmed to roomtemperature and stirred for 20 hour, then treated with a saturated solution of Na2C03 and stirred for few min. The mixture was then extracted with DCM. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; MeOH/DCM). The desired fractions were collected and the solvents evaporated in vacuo, to afford an oil that was triturated with DIPE. The resulting solid was filtered and dried to givecompound 24 (95 mg, 41% yield) as a solid. 1H NMR (400 MHz, CDC13) delta ppm 1.58 (br. s, 3 H) 4.46 (br. d, J=13.4 Hz, 1 H) 4.66 (d, J=13.4 Hz, 1 H) 4.90 (br. s., 2 H) 6.81 (s, 1 H) 7.10 (dd, J=11.8, 8.8 Hz, 1 H) 7.60 (td, J=8.3, 2.8 Hz, 1 H) 7.78 – 7.86 (m, 1 H) 7.96 (dd, J=7.1, 2.7 Hz, 1 H) 8.32 (dd, J=8.7, 4.5 Hz, 1 H) 8.45 (d, J=2.8 Hz, 1 H) 9.80 (br. s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107504-08-5, 5-Fluoro-2-picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; GIJSEN, Henricus, Jacobus, Maria; VAN GOOL, Michiel, Luc, Maria; VEGA RAMIRO, Juan, Antonio; DELGADO-JIMENEZ, Francisca; WO2012/117027; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 93349-99-6, 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. 93349-99-6, name is Methyl 5-bromo-6-methoxynicotinate, molecular formula is C8H8BrNO3, 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.

Methyl 5-bromo-6-methoxynicotinate (1 g),Ethynyltriisopropylsilane (1.5 ml),Bis (triphenylphosphine) dichloropalladium (280 mg),Copper (I) iodide (80 mg),Triethylamine (1.6 ml), And acetonitrile (15 ml)And the mixture was stirred overnight at 80 C. under a nitrogen atmosphere.The mixture was cooled to room temperature and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine,Dried over magnesium sulfate and then concentrated under reduced pressure. THF (15 ml) and 1 M tetrabutylammonium fluoride THF solution (8 ml) were added to the obtained residue, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (0.55 g)

According to the analysis of related databases, 93349-99-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MIZOJIRI, RYO; CARY, DOUGLAS ROBERT; HIRAYAMA, TAKAHARU; ITO, MASAHIRO; TANAKA, TOSHIO; IMAEDA, YASUHIRO; SASAKI, SHIGEKAZU; TAKAMI, KAZUAKI; FUKUDA, KOICHIRO; KAMAURA, MASAHIRO; MORISHITA, NAO; (133 pag.)JP2017/222626; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16063-69-7 ,Some common heterocyclic compound, 16063-69-7, molecular formula is C5H2Cl3N, 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.

General procedure: A mixture of different phenols (5.0 mmol) and K2CO3 (0.83 g, 6.0 mmol) in 15 mL DMF was stirred at room temperature for 15 min. Then, 2,4,6-trichloropyridine (Y-3) (0.91 g, 5.0 mmol) was added and the mixture was heated to 50 C. The reaction was monitored by TLC until its completion. Then, the solvent was evaporated off and the residue was dissolved in water and extracted with ethyl acetate (3 × 15 mL). Then the organic layer was dried over Na2S2O4 and concentrated in vacuo. The residue was recrystallized from ethyl acetate and petroleum ether or purified by column chromatography using ethyl acetate and petroleum ether (60-90) as an eluent to give Y-4. 4.1.3.1 2,6-Dichloro-4-(mesityloxy)pyridine (Y-4-1). Colorless crystal, recrystallized from ethyl acetate and petroleum ether, yield: 85 %, mp: 130-131 C; 1H NMR (400 MHz, CDCl3) delta: 2.06 (s, 6H, 2 × CH3), 2.31 (s, 3H, CH3), 6.66 (d, J = 1.32 Hz, 2H, Py-H), 6.93 (s, 2H, Ph-H); 13C NMR (100 MHz, CDCl3) delta: 15.99, 20.79, 109.73, 129.94, 130.09, 136.17, 147.14, 151.68, 167.27; MS-ESI: 282.3 [M+H]+, 284.2 [M+H]+. C14H13Cl2NO (281.04).

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. 16063-69-7, 2,4,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Jiapei; Chen, Wenmin; Kang, Dongwei; Lu, Xueyi; Li, Xiao; Liu, Zhaoqiang; Huang, Boshi; Daelemans, Dirk; Pannecouque, Christophe; De Clercq, Erik; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 294 – 304;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 586-98-1, 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 586-98-1 as follows.

EXAMPLE 22 Synthesis of 2-(benzo[3,4-d]1,3-dioxolan-5-yl)-4-(2-pyridylmethoxymethyl)-1,3-thiazole (Compound 27) 2-Pyridylcarbinol(0.19 ml, 1.71 mmol) was dissolved in methylene chloride(2 ml), triethylamine(0.59 ml, 4.27 mmol) was added thereto, and the mixture was stirred for 10 minutes at 0 C. Then, methanesulfonyl-chloride(0.26 ml, 3.41 mmol) was added and the resulting mixture was stirred for 10 minutes at the same temperature. The reaction solution was sequentially washed with saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, and concentrated to give 2-(methanesulfonyloxymethyl)pyridine(315 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,586-98-1, its application will become more common.

Reference:
Patent; Choongwae Pharm. Co., Ltd.; US2003/83326; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-82-3 , The common heterocyclic compound, 153034-82-3, name is 2-Fluoro-4-iodonicotinaldehyde, molecular formula is C6H3FINO, 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.

[00343] (2-Fluoro-4-iodopyridin-3-yl)methanol F OH. To a solution of 2-fluoro-4- iodonicotinaldehyde (3.50 g, 13.94 mmol) in absolute EtOH (56 mL) was added sodium borohydride (0.264 g, 6.97 mmol) at room temperature. The reaction was stirred at room temperature for 1 h, followed by the slow addition of 1 M aqueous hydrochloric acid. The product was extracted with CH2CI2 (repeated four times), and the organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. The aqueous phase was basified to pH 8-10 with 2 M aqueous sodium hydroxide and extracted with diethylether (repeated four times). Then the organic layers were combined, dried over sodium sulfate, filtered, combined with the previously obtained residue and concentrated to dryness under vacuum. The residue was used without any purification in the next step. LC/MS m/z 254[M+H]+.

The synthetic route of 153034-82-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; AUDIA, James Edmund; COTE, Alexandre; GEHLING, Victor S.; HARMANGE, Jean-christophe; HEWITT, Michael C.; LEBLANC, Yves; NAVESCHUK, Christopher G.; TAYLOR, Alexander M.; VASWANI, Rishi G.; WO2012/75383; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5435-54-1, 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. 5435-54-1, name is 3-Nitropyridin-4-ol, molecular formula is C5H4N2O3, 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.

4-Hydroxy-3-nitropyridine (10 g, 71.38 mmol) was added to 100 ml of phosphorus oxychloride. The reaction mixture was refluxed for 1 hour and then concentrated under reduced pressure. The resulting residue was added to 500 ml of ice water and then neutralized with 2N sodium hydroxide solution. The reaction mixture was extracted with 300 ml of methylene chloride. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give the titled compound (9.2 g, 92.0 %) as a pale yellow solid.[145] Rf (n-hexane/ethyl acetate = 2/1 , v/v) = 0.5[146] 1H-NMR (400MHz, CDCl ) delta 9.12(s,lH), 8.69(d,lH), 7.55(d,lH)

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 5435-54-1, 3-Nitropyridin-4-ol.

Reference:
Patent; YUHAN CORPORATION; WO2007/1139; (2007); 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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. A new synthetic method of this compound is introduced below., Product Details of 588729-99-1

Step 1. 6-Bromo-thiazolo [5,4-b] pyridin-2-yl amine:(Intermediatel) In a 50ml RB flask, 5-bromo-2-chloropyridin-3-amine (3.11 g, 15 mmol) was taken in cone. HCl (30 mL) and sonicated well to give pale brown solution. To this potassium thiocyanate (2.187 g, 22.50 mmol) was added and the resulting mixture was heated at 1000C for 6hrs .The reaction mixture was changed to pale yellow suspension after 30 minutes of reflux. The reaction mixture was evaporated in vacuo; ice-cold water was added to the residue, sonicated well and neutralized with saturated sodium carbonate under cooling condition. The precipitated solid was sonicated well, filtered and dried under high vacuum afforded the product as off-white solid (2.5gm)MS (ES+): 231 Rw C6H4BrN3S1H NMR 5(DMSO-dfi): 5.85 (bs, 2H,NH2); 7.3 (s, lH,Aro); 7.65 (s, lH,Aro).

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, 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 246847-98-3, 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. 246847-98-3, name is 5-Chloro-3-fluoropyridin-2-amine. A new synthetic method of this compound is introduced below.

To concentrated sulfuric acid (100mL) cooled to -10 was added 2-amino-3-fluoro-5-chloropyridine (10 g, 68.2 mmol) with stirring. After dissolution, the mixture was continued to stir at -10 for 15min. Then 50 mL 30%hydrogen peroxide solution was added slowly, and the reaction temperature was maintained below 0. The mixture was warmed to room temperature and stirred for 72h, then poured into 500 mL 13%ice brine with stirring and extracetd with 200mL EA for three times. The combined organic extracts were washed with saturated sodium bicarbonate solution until the aqueous phase was alkaline, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to give the desired product 2-nitro-3-fluoro-5-chloropyridine (2.8g, 23.3%) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,246847-98-3, 5-Chloro-3-fluoropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; FUJIAN HAIXI PHARMACEUTICALS CO., LTD; FENG, Yan; WANG, Ruyong; LI, Junqing; ZHENG, Jianjia; LIAN, Xin; GONG, Xuan; FU, Yueli; KANG, Xinshan; (144 pag.)WO2019/174601; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 186593-43-1, 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.186593-43-1, name is 5-Amino-3-bromo-2-methylpyridine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.

Step 1: EDC (1.3 equiv.) was added to a solution of 5-bromo-6-methylpyridin-3-amine (1.05 equiv), 2-(2-cyanopropan-2-yl)isonicotinic acid (1.0 equiv), HOAt (1.3 equiv) in DMF (0.17 M). The mixture was stirred at ambient temperature 3 hrs. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with 1M aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated. The crude was purified by ISCO(50% EtOAc/Heptane). Combined fractions still contained 17% 5-bromo-6-methylpyridin-3-amine. Add 2-(2-cyanopropan-2-yl)isonicotinic acid (0.3 equiv), EDC (0.3 equiv), HOAt (0.3 equiv) in DMF (0.17 M). After stirred at rt overnight, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with 1M aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated to yield N-(5-bromo-6-methylpyridin-3-yl)-2-(2-cyanopropan-2-yl)isonicotinamide in 71% over three steps. LCMS (m/z) (M+H)=359.0, Rt=0.73 min.

Statistics shows that 186593-43-1 is playing an increasingly important role. we look forward to future research findings about 5-Amino-3-bromo-2-methylpyridine.

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