Category: pyridine-derivatives

Application of 116026-95-0, 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 116026-95-0, name is tert-Butyl (4-formylpyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(llH)-dione 6-oxime (80.0 mg, 0.333 mmol), ammonium acetate (0.513 g, 6.66 mmol) , water (0.12 mL) and acetic acid (0.76 mL) was stirred at 80 0C for 3 h. The solution was diluted with ethyl acetate and water, the organic solution was washed with brine, dried over MgSO4 and concentrated. The crude residue was purified by preparative LCMS to yield the desired product (102 mg, 69%). LCMS for C23H22N7O3(MH-H)+: m/z = 444.2.

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 116026-95-0, tert-Butyl (4-formylpyridin-3-yl)carbamate.

Reference:
Patent; INCYTE CORPORATION; WO2007/38215; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20970-75-6, 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. 20970-75-6, name is 2-Cyano-3-methylpyridine, molecular formula is C7H6N2, 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; 3-Cycloheptyl-8-((2,6-dichlorophenoxy)methyl)H-imidazo[1,5-a]pyridine; Compound 1A: 3-(Bromomethyl)picolinonitrile To a solution of 3-methylpicolinonitrile (660 mg, 5.6 mmol) in 20 mL of carbon tetrachloride was added NBS (1 g, 5.6 mmol) and dibenzoyl peroxide (200 mg, 0.83 mmol) at RT. The reaction mixture was heated at 80 C. for 2 hr, and then cooled to RT. The resulting solid was filtered off, and the filtrate was concentrated under reduced pressure to provide a residue. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated under reduced pressure to provide crude material. The crude material was purified via silica gel chromatography (10% ethyl acetate in hexanes) to provide compound 1A (510 mg, 46%) as a pale yellow oil. HPLC Rt (Method A): 1.72 min. LC/MS (m/z)=197 (M+H)+.

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 20970-75-6, 2-Cyano-3-methylpyridine.

Reference:
Patent; Li, James J.; Hamann, Lawrence G.; Wang, Haixia; US2006/281750; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60154-05-4, 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.60154-05-4, name is 5-Iodo-1-methylpyridin-2(1H)-one, molecular formula is C6H6INO, molecular weight is 235.0224, as common compound, the synthetic route is as follows.

5 -((tert-butyldimethylsilyl)oxy)-6-chloro- 1H-indazole (0.70 g) and 5 -iodo- 1-methylpyridin-2(1H)-one (Example 1, Step B) (0.64 g, 2.7 mmol) were mixed in toluene(2 mL) and heated gently to dissolve at 50C. The resulting mixture was evacuated andpurged with N2 several times. Potassium phosphate (0.43 mL, 5.2 mmol) and (1S,2S)-cyclohexane-1,2-diamine (0.060 mL, 0.50 mmol) were added, followed by copper(I) iodide (0.028 g, 0.15 mmol). The mixture was then heated to 110C for 19 hr. Afterward, the mixture was cooled to room temperature and diluted with ethyl acetate (120 mL), washed with 1M HC1 (50 mL), and saturated ascorbic acid (30 mL). The organic andaqueous layers were separated on a phase separator. The organic layer was concentrated to yield 1.2 g of the title product as a purple/brown oil that was used in the next step without further purification.

Statistics shows that 60154-05-4 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-1-methylpyridin-2(1H)-one.

Reference:
Patent; ASTRAZENECA; RIPA, Lena, Elisabeth; LAWITZ, Karolina; LEPISTOe, Matti, Juhani; HEMMERLING, Martin; EDMAN, Karl; LLINAS, Antonio; (96 pag.)WO2016/46260; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72141-44-7, 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 72141-44-7, name is 4-Chloro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

INTERMEDIATE 37 4-(3 -Bromo-4-methyl- 1 H-pyrazol- 1 – yl)-2-methoxyp yridine To 3-bromo-4-methyl-lH-pyrazole (200 mg, 1.24 mmol) in DMSO (1.2 mL) at 0 C, was added sodium hydride (60% in mineral oil, 55 mg, 1.37 mmol). The reaction was warmed to 25 C and stirred for 60 min before 4-chloro-2-methoxypyridine (178 mg, 1.24 mmol) was added. The reaction mixture was stirred at 85 C overnight. The reaction mixture was quenched by the addition of water and was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3-bromo-4-methyl-lH-pyrazol-l -yl)-2- methoxypyridine, as a white solid. LCMS calc. = 268.00; found = 267.99 (M+H)+. NMR (500 MHz, CDCI3): delta 8.16 (d, J= 5.8 Hz, 1 H); 7.69 (s, 1 H); 7.23-7.15 (m, 1 H); 6.95 (s, 1 H); 3.96 (s, 3 H); 2.08 (s, 3 H).

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 72141-44-7, 4-Chloro-2-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); 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.73841-32-4, name is 3-Iodopicolinic acid, molecular formula is C6H4INO2, molecular weight is 249.01, as common compound, the synthetic route is as follows.Application In Synthesis of 3-Iodopicolinic acid

Description 2; Methyl 3-iodo-2-pyridinecarboxylate (D2); A mixture of D1 (3.Og, 0.012mol) and CH2SO4 (2ml) in MeOH (100ml) was heated at65°C for 18 h. After this period, solvents were evaporated in vacuo and the residue basified with solid NaHCO3. The residue was then extracted with EtOAc (3x100ml). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound (2.2g, 70percent). deltaH (CDCI3, 250MHz) 4.01 (3H, s), 7.13 (1 H, dd), 8.29 (1H, dd), 8.64 (1H, dd). MS (ES): C7H6INO2 requires 263; found 264 (MH+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73841-32-4, 3-Iodopicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/7018; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 39891-09-3 ,Some common heterocyclic compound, 39891-09-3, molecular formula is C7H5ClN2, 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 solution at-5 C of 44 mL of absolute ethanol in 155 mL of chloroform under nitrogen was added dropwise 45 mL of acetyl chloride. After 0.5 hours a solution of 8.46 g (55.4 MMOL) of Preparatory Compound E in 71 mL of chloroform was added dropwise keeping the temperature at 0 C or below. The mixture was then kept at 0 C for 4 hours and was then allowed to warm to room temperature overnight (about 22 C). Ethyl ether was added (350 mL) with cooling and the mixture was stirred for several minutes and was then filtered through a medium porosity sintered glass funnel always careful to keep a layer of ether over the white solid. After washing with an ample amount of ether, the solid/ether mixture was washed into a 1 L three-neck round-bottomed flask fitted with a mechanical stirrer and was then diluted with 400 mL of ether and was treated dropwise with 12.34 g (122 mmol, 2.2 equiv. ) of triethylamine in ether while cooling. The contents were stirred overnight under nitrogen. The mixture was filtered, the filtrate was dried over sodium sulfate and was concentrated to give 9.91 g (90%) of Preparatory Compound K, ethyl 2- (6-CHLORO-3-PYRIDINYL) ethanimidoate, as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39891-09-3, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; WO2004/57960; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58553-48-3, 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. 58553-48-3, name is 5-(Hydroxymethyl)picolinonitrile, molecular formula is C7H6N2O, 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 32A (6-Cyanopyridin-3-yl)methyl methanesulphonate; 3.51 ml (27.14 mmol) of N,N-diisopropylethylamine and 2.87 ml (25.05 mmol) of methanesulphonic acid chloride were added successively to a solution of 2.8 g (20.87 mmol) of 5-(hydroxymethyl)pyridine-2-carbonitrile [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 50 ml of anhydrous dichloromethane at 0 C. The reaction mixture was then stirred at RT for 1 h. 10 ml of water were then added, the phases were separated and the aqueous phase was extracted twice with approx. 10 ml of dichloromethane each time. The combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and freed from the solvent on a rotary evaporator. The residue obtained was separated into its components by MPLC (silica gel, cyclohexane/ethyl acetate 1:1). 2.12 g (48% of theory) of the title compound (for the analytical data see below) and 1.51 g (47% of theory) of the compound described in Example 31A were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 8.76 (d, 1H), 7.93 (dd, 1H), 7.78 (d, 1H), 5.32 (s, 2H), 3.10 (s, 3H).MS (DCI, NH3): m/z=213 [M+H]+, 230 [M+NH4]+.LC/MS (method F, ESIpos): Rt=0.57 min, m/z=213 [M+H]+.

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 58553-48-3, 5-(Hydroxymethyl)picolinonitrile.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/312930; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 97944-43-9, 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 97944-43-9, name is 3-Bromo-5-methylpyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-bromo-5-methylpyridine-4-amine (5.00 g, 27 mmol), (0231) isopropenylboronic acid pinacol ester (6.70 g, 40 mmol), Pd(PPh3)4 (3.20 g, 2.70 mmol), l,4-dioxane (50 mL), and NaHCCh (sat. aq., 50 mL) was stirred under reflux for 16 h. Then the suspension was cooled and diluted with water and DCM until clear phase separation. The aqueous phase was extracted with DCM. The combined organic extracts were dried (MgS04), filtered and concentrated under reduced pressure. The crude mixture was purified by flash column chromatography (silica, mobile phase gradient: 0-3% 7N NFT/McOH in DCM). The residue was combined with another fraction (1.5 g) and dissolved in z-PrOH (20 mL). The mixture was treated with HC1 (6M in z-PrOH, 9 mL, 54 mmol) and stirred over the weekend. The mixture was ice- cooled and the product was collected by filtration to afford 1-67 (4.5 g, 76%) as a white solid.

According to the analysis of related databases, 97944-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; LEENAERTS, Joseph, Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; MARTINEZ LAMENCA, Carolina; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (110 pag.)WO2019/243533; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1254073-41-0, 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. 1254073-41-0, name is 5-Fluoropicolinohydrazide. A new synthetic method of this compound is introduced below.

Into a solution of 5-fluoropyridine-2-carbohydrazide (1 g) in dichloromethane (30 mL) was mixed triethylamine (2.7 mL), and methyl chloroglyoxylate (0.59 mL) was added thereto under ice-cooling, followed by stirring at room temperature for 5 hours. p-Toluenesulfonyl chloride (1.23 g) was added thereto under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture was added water at room temperature to carry out liquid separation, and the organic layer was concentrated. After concentration, the obtained oily substance was dissolved in ethyl acetate. Together with the aqueous layer, liquid separation was carried out. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The obtained solid was collected by filtration while washing with a solvent (hexane:ethyl acetate=4:1) to obtain methyl 5-(5-fluoropyridin-2-yl)-1,3,4-oxadiazole-2-carboxylate (1.073 g) as a gray solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1254073-41-0, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; EP2511265; (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. 1122-61-8, name is 4-Nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Nitropyridine

General procedure: Nitroarene (0.5 mmol) and Pt-BNP 3 (9.8 mg, 2.5 mol%, 25 wt% of Pt by ICP-OES analysis) were taken in an oven dried reaction tube equipped with magnetic pellet. Water (2.0 mL)was added to the reaction tube and the resulting reaction mixture was stirred at room temperature under hydrogen atmosphere (using H2 balloon) and the reaction was monitored by TLC. After consumption of the starting material, crude product was extracted with ethyl acetate (3 × 20 mL). Then the organic phase was dried over Na2SO4 and concentrated in vacuum. The product was further purified by column chromatography using silica gel to yield pure aniline.

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, 1122-61-8, 4-Nitropyridine.

Reference:
Article; Kotha, Surya Srinivas; Sharma, Nidhi; Sekar, Govindasamy; Tetrahedron Letters; vol. 57; 13; (2016); p. 1410 – 1413;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem