Pyridine-derivatives

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

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

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

Reference of 10366-35-5 ,Some common heterocyclic compound, 10366-35-5, molecular formula is C6H5ClN2O, 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 3 2-[4-(2,3-Dihydroxypropyl)piperazin-1-yl]nicotinamide Operation was carried out in a manner similar to the one described in Example 2, using 1.6 g of 2-chloronicotinamide, 3.2 g of 1-(2,3-dihydroxypropyl)piperazine and 30 ml ethanol and refluxing overnight. Column purification of the residue gave 1 g of 2-[4-(2,3-dihydroxypropyl)piperazin-1-yl]nicotinamide, which, recrystallized from acetone, melted at 140-142C.

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. 10366-35-5, 2-Chloronicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOMPE’ FARMACEUTICI S.p.A.; EP230402; (1993); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 30766-11-1 , The common heterocyclic compound, 30766-11-1, name is 5-Bromopicolinic acid, molecular formula is C6H4BrNO2, 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.

To a mixture of 5-bromopyridine-2-carboxylic acid (2.5 g, 12 mmol) in methylene chloride (10.0 mL) was added oxalyl chloride (1.6 mL, 18 mmol), followed by N,N-dimethylformamide (0.020 mL, 0.26 mmol). After stirred at RT for 2 h, the mixture was evaporated under reduced pressure. The residue was the acid chloride which was used directly in next step reaction.

The synthetic route of 30766-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhuo, Jincong; Qian, Ding-Quan; Yao, Wenqing; US2007/129345; (2007); 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. 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, the common compound, a new synthetic route is introduced below. Safety of Methyl 6-chloro-5-nitronicotinate

Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl 2-(benzylamino)acetate (6.0 g, 31.05 mmol) neat while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30percent gradient, ethyl acetate in hexanes) to yield the title compound (3.10 g, 90percent yield) as a yellow oil. [M+H] calc’d for C18H19N3O6, 374; found, 374.

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2010/190763; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 754214-42-1, 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic 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, Product Details of 754214-42-1, blongs to pyridine-derivatives compound. Product Details of 754214-42-1

A suspension of 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (250 mg, 1.5 mmol) in N,N-dimethylformamide (5 mL) was warmed to 40 C. N-chlorosuccinimide (243 mg, 1.62 mmol) was added and the mixture was stirred at 55 C. for 5 hours. The reaction was cooled to room temperature and left stirring for 2 days. The mixture was diluted with water (20 mL) and stirred overnight. The resulting solid was collected by filtration and dried to give the title compound (161 mg, 55%). +ESI (M+H) 197.1; 1H NMR (400 MHz, DMSO-d6, delta): 13.08 (br. s., 1H), 12.39 (br. s., 1H), 8.86 (d, J=1.8 Hz, 1H), 8.40 (d, J=1.2 Hz, 1H), 7.84 (d, J=2.5 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,754214-42-1, 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US2012/108619; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-98-0, 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.13534-98-0, name is 4-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.

General procedure: Step 1: A vial equipped with a magnetic stir bar was charged with the orthohaloaminopyridineand BrettPhos G1 precatalyst (6 mol %). The vial was sealedwith a teflon screw cap, and evacuated and backfilled with argon three times. Theamine (1 to 1.5 mol eq) was added via syringe, followed by LiHMDS solution (1M in THF, 2.5 mol eq). Amines that were solid at room temperature were addedwith the catalyst. The reaction mixture was stirred at 40 C for 4-18 h, until LC/MSindicated complete conversion of the starting material. The mixture was cooled toroom temperature, diluted with dichloromethane, and poured into water. Theorganic phase was separated and the aqueous phase was extracted twice more withdichloromethane. The combined organic phases were dried over Na2SO4. Thesolvent was removed under reduced pressure.

The chemical industry reduces the impact on the environment during synthesis 13534-98-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Chaomin; Chen, Lily; Steinhuebel, Dietrich; Goodman, Andrew; Tetrahedron Letters; vol. 57; 25; (2016); p. 2708 – 2712;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1052714-46-1, 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.1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid, molecular formula is C6H3BrFNO2, molecular weight is 219.9959, as common compound, the synthetic route is as follows.

To a solution of 6-bromo-5-fluoropicolinic acid (1.0 equiv.) in methanol (0.2 M) was added H2SO4 (4.2 equiv.) and the reaction was stirred at room temperature for two hours. Upon completion of the reaction as monitored by LC/MS, the reaction was diluted with ethyl acetate and quenched slowly with saturated aqueous NaHCO3. The reaction was poured into a separatory funnel and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered, and concentrated in vacuo to provide methyl 6-bromo-5-fluoropicolinate as a white solid (>99%). LC/MS=233.9/235.9 (M+H), Rt=0.69 min.

The chemical industry reduces the impact on the environment during synthesis 1052714-46-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Burger, Matthew; Nishiguchi, Gisele; Machajewski, Timothy D.; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225062; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 504-29-0, 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. 504-29-0, name is Pyridin-2-amine, molecular formula is C5H6N2, 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.

2-Aminopyridine (3.1g, 33mmol) and triethylamine(6.9mL, 49mmol) was dissolved in dichloromethane (40mL), 2,2-dimethylpropionyl chloride (4.5mL, 36mmol) was added on an ice bath, and the solution was stirred for 2 hours at the same temperature. Water was added thereto for extraction, the organic layer was sequentially washed with an aqueous solution of saturated sodium bicarbonate and brine, then, dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the title compound (6.0g, 34mmol, 102%) was obtained as a white solid. 1H-NMR Spectrum (CDCl3) delta(ppm) :1.27 (9H, s), 7.03 (1H, ddd, J=1.1, 4.9, 7.3Hz), 7.68-7.72 (1 H, m), 8.02 (1 H, s), 8.23-8.27 (2H, m).

According to the analysis of related databases, 504-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem