Pyridine-derivatives

Application of 585-48-8 ,Some common heterocyclic compound, 585-48-8, molecular formula is C13H21N, 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 197 (R)-N-(2-Chloro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide Oxalyl chloride (1.07 ml) was added dropwise to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (Method 9) (1.95 g) in DCM (42 ml) and DMF (0.8 ml). The mixture was stirred at ambient temperature for 2 hours and was then added over 35 minutes to a solution of 2-chloro-4-iodoaniline (2.5 g) and 2,6-di-t-butylpyridine (2.94 ml) in DCM (40 ml) and stirred a further 18 hours. Volatile material was removed by evaporation and the residue was purified by flash chromatography on silica gel eluding with DCM to give the title compound (2.85 g) as a solid. NMR: 1.6 (s, 3H), 7.7 (m, 2H), 7.8 (d, 1H), 7.9 (brs, 1H); MS (ESP-): 392.

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. 585-48-8, 2,6-Di-tert-butylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US6498275; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 109-04-6 , The common heterocyclic compound, 109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, 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 109 B2-(tributylstannyl)pyridine; 2-bromopyridine (14.9 g, 93.1 mmol) in anhydrous THF (700 mL) was cooled to -78 C. under a stream of nitrogen gas, n-BuLi in hexane (54 mL) were added thereto and the mixture was stirred for 30 min. Tributyltin chloride (29 mL, 108 mmol) was added and the mixture was stirred, at -78 C. for 2 hours and afterwards at -20 C. for 3 hours. It was poured into an aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried and the solvent was evaporated. The residue was purified by chromatography (petroleum ether/ethyl acetate=9/1) to give 2-(tributylstannyl)pyridine (12 g, yield 34%) as a yellow liquid, LC-MS (ESI) m/z: 370 (M+1)+.

The synthetic route of 109-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEAD THERAPEUTICS, INC.; US2009/197863; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 108-99-6, 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 108-99-6, name is 3-Methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

The catalyst was prepared by the method as described in Example 3 and process conditions were maintained as per Example 5 except that the process was carried out at large scale. The catalyst was packed as per Example 5 in a tubular reactor. Total volume of the reactor was 75 liters and equipped with heating and cooling arrangement. The catalyst bed was heated in the presence of air/nitrogen to 250 C. beta-picoline, water and air were fed separately through a vaporizer from top of the reactor. The molar feed ratio of oxygen:water:beta-picoline was 20:40:1 and WHSV was 0.05 hr-1. The nicotinic acid was isolated by the method as described in Example 4. The vent gases and scrubbed liquid obtained from secondary absorber and mother liquor of first absorber was recycled back in the process with optimum purge. The nicotinic acid obtained was white colored. Selectivity: 90.8%; beta-picoline conversion of 94.6%. Assay: 99.58%.

According to the analysis of related databases, 108-99-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JUBILANT LIFE SCIENCES LTD; US2012/65405; (2012); 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. 128071-98-7, name is 4-Bromo-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Bromo-2-fluoropyridine

The stirred solution of 4-bromo-2-fluoropyridine (10.0 g, 56.82 minol), phenylmethanethiol (7.3 mL, 62.50 minol), Pd2(dba)3 (2.60 g, 2.84 minol), Xanthophos (3.28 g, 5.68 minol) andDIPEA (19.4 mL, 113.64 minol) in dioxane (150 mL) was degassed with argon for 15 min The resulting reaction mixture was heated to reflux for 16 h under argon atmosphere. The reaction mixture was cooled to rt, filtered through celite bed, the celite bed was washed with EtOAc and the combined filtrate was concentrated to dryness under reduced pressure. The crude was purified by flash column chromatography (40 g SiliCycle column, 2-3% EtOAc inHexane elution) to provide the title compound as yellow oil (12.0 g, 96.3%). LC/MS, ESIMS( ): 219.5. 1H NMR (400 MHz, CDCI3) O ppm 7.99 (d, J= 5.2 Hz, 1H), 7.43-7.30 (m, 5H), 7.00 -6.98 (m, 1 H), 6.74 -6.73 (m, 1 H).

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, 128071-98-7, 4-Bromo-2-fluoropyridine.

Reference:
Patent; NOVARTIS AG; PHILLIPS, Dean Paul; AZIMIOARA, Mihai; CHEN, Bei; EPPLE, Robert; NIKULIN, Victor Ivanovich; RODRIGUEZ, Rodrigo A.; PATEL, Sejal; HONDA, Ayako; (295 pag.)WO2018/42316; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18364-47-1, Adding some certain compound to certain chemical reactions, such as: 18364-47-1, name is N-Methylpyridin-3-amine,molecular formula is C6H8N2, 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 18364-47-1.

12.71 g (104.7 mmol) of thionyl chloride were added to a suspension of 12 g (95.2 mmol) of 1-methylimidazole-5-carboxylic acid in 72 ml of toluene, and the mixture was stirred under reflux overnight. The reaction mixture was concentrated under reduced pressure. A solution of 10.3 g (95.2 mmol) of 3-methylaminopyridine (V-1) in 72 ml of pyridine was added to the residue, and the resulting reaction mixture was heated at 115 C. for 4 h. The mixture was then once more concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using the mobile phase acetonitrile/methanol 3:1. This gave 8.1 g (39.3% of theory) of the title compound (XV-1). log P[n]: 0.42 (0537) 1H-NMR (CD3CN, 400 MHz); delta=3.39 (s, 3H), 3.81 (s, 3H), 6.17 (s, 1H), 7.36-7.40 (m, 2H), 7.67-7.70 (m, 1H), 8.41 (m, 1H) 8.47 (m, 1H) ppm.

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. 18364-47-1, N-Methylpyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; JANSEN, Johannes-Rudolf; HEIL, Markus; FISCHER, Reiner; WILCKE, David; WILLOT, Matthieu; ILG, Kerstin; EILMUS, Sascha; LOeSEL, Peter; ANDERSCH, Wolfram; (69 pag.)US2019/47982; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.55876-84-1, name is Methyl 5-(bromomethyl)picolinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.Recommanded Product: Methyl 5-(bromomethyl)picolinate

INTERMEDIATE 38 – PREPARATION of methyl 5-(3-fluorobenzyl)picolinate. A mixture of 3-fluorophenylboronic acid (0.319 g; 2.28 mmol), methyl 5- (bromomethyl)picolinate (0.350 g; 0.230 mmol), tetrakis-(triphenylphosphine)-palladium(0) (0.175; 0.152 mmol) and N,N diisopropylethylamine (0.524 g; 3.04 mmol) in dimethoxyethane (9 mL) and water (3 mL) was irradiated in a microwave oven at 130°C for 20 minutes. The resulting solution was partitioned between water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 1 to 10 percent ethyl acetate in dichlomethane) to afford 0.149 g (40percent) of the title compound as a yellow oil.ESI/APCI(+): 246 (M+H), 268(M+Na).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55876-84-1, Methyl 5-(bromomethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&D; REMYND; GRIFFIOEN, Gerard; VAN DOOREN, Tom; ROJAS DE LA PARRA, Veronica; ALLASIA, Sara; MARCHAND, Arnaud; KILONDA, Amuri; CHALTIN, Patrick; WO2012/80221; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.7321-93-9, name is 4,6-Dichloropyridin-3-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.COA of Formula: C5H4Cl2N2

To a stirred solution of 4,6-dichloropyridin-3-amine (1.42 g, 8.712 mmol) in dry DMF (8 mL) was added a 60percent suspension of sodium hydride in mineral oil (767 mg, 19.166 mmol) under nitrogen atmosphere at 0 °C. The reaction mixture was stirred at this temperature for 5-10 min. To this stirred reaction mixture was added a solution of methyl iodide (1.2 mL, 19.166 mmol) in dry DMF (2 mL) dropwise. Then, the reaction mixture was stirred at RT for 20 min. The progress of reaction was monitored by TLC. After completion of the reaction, the mixture was quenched by addition of ice-water and product was extracted with EtOAc (50 mL). The organic layer was again washed with water (2×20 mL) and brine solution (20 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 4,6-dichloro-N-methyl-pyridin-3-amine (1.6 g) as a light brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7321-93-9, 4,6-Dichloropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; PUJALA, Brahmam; SHINDE, Bharat Uttam; NAYAK, Anjan Kumar; CHAKLAN, Naveen; AGARWAL, Anil Kumar; RAMACHANDRAN, Sreekanth A.; PHAM, Son; WO2015/103355; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6221-01-8, Pyridine-2,5-dicarbaldehyde, 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, Computed Properties of C7H5NO2, blongs to pyridine-derivatives compound. Computed Properties of C7H5NO2

General procedure: To a solution of 2,5-dicarbaldehyde pyridine (50 mg), in 1,2-dichloroethane (3.6 mL), was added the aniline derivative (6 eq) and acetic acid (2 eq) were added. After stirring for 5 min at room temperature, the solution was treated with sodium triacetoxyborohydride (3 eq). It was then stirred at room temperature overnight and purified via preparative thin layer chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6221-01-8, Pyridine-2,5-dicarbaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Virani, Saniya; Liang, Zhongxing; Yoon, Younghyoun; Shim, Hyunsuk; Mooring, Suazette R.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 220 – 224;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 920979-04-0, 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. 920979-04-0, name is 2-Iodo-6-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4F3IN2, 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.

10.2 (5-Trifluoromethyl)pyrrolo[3,2-b]pyridine-2-carboxylic acid; 0.5 g (1.74 mmol) of 3-amino-2-iodo-6-(trifluoromethyl)pyridine, obtained in Stage 10.1, 0.45 g (5.21 mmol) of pyruvic acid, 0.51 mL (5.21 mmol) of 1,4-diazabicyclo[2.2.2]octane and 10 mL of dry dimethylformamide are introduced, under argon, into a sealed tube. The solution is degassed for some minutes, then 0.19 g (0.87 mmol) of palladium acetate is added, the tube is closed and it is refluxed at 130 C. for 4 hours. The cooled solution is then concentrated at reduced pressure and the residue is taken up in 100 mL of ethyl acetate. The organic phase is extracted successively with 2×50 mL of an aqueous solution of 2N sodium hydroxide. The basic aqueous phases are combined, cooled to 0 C., acidified with additions of hydrochloric acid and then extracted with 4×50 mL of ethyl acetate. These organic phases are combined, washed with 20 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated at reduced pressure. We obtain 0.22 g of product, which is used as it is in the next stage.

According to the analysis of related databases, 920979-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2010/41634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 152684-30-5 ,Some common heterocyclic compound, 152684-30-5, molecular formula is C6H5BrN2O3, 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.

AL 2-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-L3,2-dioxaborolan-2-yl)pyridine; To a dry flask was added 5-bromo-2-methoxy-3-nitropyridine (1.3 g, 5.0 mmol),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.6 g, 6.4 mmol), and Pd(dppf)Cl2 (0.2 g, 0.25 mmol). Potassium acetate (1.5 g, 15 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (30 mL) was added and the reaction was heated at 80 0C in an oil bath overnight. The reaction mixture was evaporated to dryness. The residue was dissolved in ethyl acetate (20 mL) and washed with water (20 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting material was purified by silica gel chromatography (eluting with 0-50% ethyl acetate in hexane) to yield the product (0.2 g, 15%). ESI-MS m/z calc. 280.12, found 199.1 (MW[-C6Hio]+l)+. Retention time 0.7 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,152684-30-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/141119; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem