Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, 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 C7H6FNO, blongs to pyridine-derivatives compound. Computed Properties of C7H6FNO

To a stirred solution of 3-fluoro-4-acetylpyridine (5.3 g, 38.1 mmol) in glacial acetic acid (14 mL) and 48% hydrobromic acid (5.3 mL), bromine (2 mL, 38 mmol) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60 C. for 2.5 h then it was cooled down and ethylacetate (70 mL) was added. After 30′ stirring the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtained in 82% yield (9.4 g). 1H NMR (DMSO-d6/400 MHz) delta ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (dd, 1 H) 8.81 (d, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142414; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, 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. Safety of 5-(Trifluoromethyl)pyridin-3-amine

To a mixture of 2-(4-bromo-2,5-difluoro-phenyl)acetic acid (9, 2.16 g, 8.60 mmol), 5-(trifluoromethyl)pyridin-3-amine (10, 1.39 g, 8.57 mmol) and pyridine (2.09 ml, 25.8 mmol) in ethyl acetate (85 ml) was added slowly propylphosphonic anhydride (50 wt % solution in ethyl acetate, 10.1 ml, 17.2 mmol). The reaction mixture was allowed to stir at room temperature for 3 hours. The reaction was diluted with ethyl acetate and was washed with saturated aqueous ammonium chloride, water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to provide 3.29 g (97% yield) of compound 11 that was used in the next step without further purification. MS ESI [M+H+]+=397.05.

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; Plexxikon Inc.; Lin, Jack; Ibrahim, Prabha N.; Albers, Aaron; Buell, John; Guo, Zuojun; Pham, Phuongly; Powers, Hannah; Shi, Songyuan; Spevak, Wayne; Wu, Guoxian; Zhang, Jiazhong; Zhang, Ying; (132 pag.)US2017/267660; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3678-62-4 ,Some common heterocyclic compound, 3678-62-4, molecular formula is C6H6ClN, 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.

10 g of 2-chloro-4-methylpyridine are dissolved in 30 ml of CH3CN and a mixture of AIBN (3 g) and NCS (30 g) is added. The resulting mixture is refluxed for 4 hours. After removing the solvent, the crude product is further purified by distillation (boiling point: 70 C., 20 mtorr)

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. 3678-62-4, 2-Chloro-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2004/248884; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886365-06-6, 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 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate Example Int15.17.045-bromo-4-methylpyridine-2-carboxylic acid To a stirred solution of Int15.17.03 (1 .0 g) in THF (20 mL), methanol (5 mL) and water (5 mL) was added an aqueous solution of lithium hydroxide (6.1 mL; c = 1M). The mixture was stirred at r.t. for 1 h. Aqueous hydrochloric acid was added, until pH 4 was reached. The mixture was extracted with chloroform using a continous liquid /liquid extractor (from Normag Labor- und Prozesstechnik GmbH, llmenau, Germany) for 16 h. The solvent was removed in vacuum to give 870 mg of the title compound.

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 886365-06-6, Methyl 5-bromo-4-methylpicolinate.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; SCHIROK, Hartmut; BRIEM, Hans; WO2012/143329; (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. 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6FNO

Example 100: 3-(4-Chlorophenylsulfonylmethyl)-2-fluoropyridine A chloroform (10 ml) solution of (2-fluoropyridin-3-yl)methanol (49 mg, 0.385 mmol) and thionyl chloride (0.14 ml, 1.93 mmol) was stirred at 50C for 3.5 hours.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. The residue thus obtained was dissolved in butanol (5 ml), followed by the addition of sodium 4-chlorobenzenesulfinate (92 mg, 0.462 mmol) and potassium acetate (76 mg, 0.770 mmol).. The mixture was stirred at 70 to 80C for 12 hours.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. ethyl acetate was added to the residue, and the mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, and then, dried over anhydrous sodium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash chromatography on a silica gel column.. The fraction obtained from the hexane:ethyl acetate (=2:1) elude was concentrated under reduced pressure, whereby the title compound (59 mg, 54%) was obtained as a white solid. IR (ATR) nu: 3097, 2989, 2933, 1643, 1606, 1573, 1469, 1434, 1409, 1392, 1321, 1276, 1240, 1184, 1170, 1149, 1083, 1010, 956, 902, 842, 813, 779, 763, 725, 696, 640, 582, 541, 522, 480, 445 cm-1.1H-NMR (400MHz, CDCl3) delta: 4.38(2H,s), 7.21-7.30(1H,m), 7.47(2H,d,J=8.8Hz), 7.61(2H,d,J=8.8Hz), 7.87-7.94(1H,m), 8.19-8.25(1H,m). MS (m/z): 286 (M++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, 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 195044-14-5, 2-Bromo-6-tert-butylpyridine, 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, Quality Control of 2-Bromo-6-tert-butylpyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-6-tert-butylpyridine

Step-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (90 mg, 0.719 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (184.7 mg, 0.862 mmol, 1.2 eq) in 1,4 dioxane (3 mL) was added potassium carbonate (198.7 mg, 1.438 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (27.38 mg, 0.143 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (25.35 mg, 0.287 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resulting mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). The combined organic layers were washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 30% EtOAc/Hexane to afford pure 1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-2-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (180 mg, 63.15%) as off white solid.

The synthetic route of 195044-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1198416-32-8, 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.1198416-32-8, name is 2-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C14H11BrN2O2S, molecular weight is 351.22, as common compound, the synthetic route is as follows.

A mixture of 209-3 (30 g, 0.085 mol), methanol (85OmL) and aqueous potassium hydroxide (5 mol/L, 100 mL) was heated under reflux overnight. The majority of the solvent was removed under vacuum, and the residue was partitioned between EtOAc and water. The organic layer was dried over anhydrous Na2SO4 and concentrated to give 209-4 (24 g, 80% yield) which was used without further purification. 1H NMR (400 MHz, DMSO): 6.550 (s, 1H); 7.039 (dd, J=5.2 Hz, J=3.2 Hz, 1H); 7.857 (dd, J=1.6 Hz, J=3.2 Hz, 1H); 8.155 (q, J=1.6 Hz, 1H); 12.418 (br, 1H)

Statistics shows that 1198416-32-8 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; INTERMUNE, INC.; US2009/318455; (2009); 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. 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine, the common compound, a new synthetic route is introduced below. Quality Control of 2,6-Dimethyl-3-hydroxypyridine

Example 150 5-[3-(2,4-Bis-trifluoromethyl-phenyl)-6-methyl-pyridin-2-ylmethyl]-2-(2,3-difluoro-phenyl)-5H-imidazo[4,5-d]pyridazine (Compound 336) 2,6-Dimethyl-pyridin-3-ol (1 g) was dissolved in pyridine (20 mL) and triflic anhydride (1.5 mL) was added. After 3 hr of stirring the reaction was evaporated and chromatographed to give quantitatively trifluoro-methanesulfonic acid 2,6-dimethyl-pyridin-3-yl ester.

The synthetic route of 1122-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genelabs Technologies, Inc.; US2009/226398; (2009); 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. 128071-77-2, name is 4-Bromo-2-fluoronicotinaldehyde, the common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrFNO

Intermediate 25A4-bromo- I -(2-fluorophenyl)- I H-pyrazolo[3,4-b]pyridine 3.70 g (18.14 mmo[) 4-Bromo-2-f[uoronicotina[dehyde and 2.29 g (18.14 mmo[) (2- f[uoropheny[)hydrazine were disso[ved in 82.6 mL 2-methy[propanenitri[e. After addition of 17.74 g (54.44 mmo[) cesium carbonate the reaction mixture was stirred for 4 hours at room temperature to a[[ow comp[ete reaction to the intermediatehydrazone (safety reasons). Stirring was now continued over night at 120 C. Due to an incomp[ete reaction stirring was continued for 65 hours at 120 C. The reaction mixture was di[uted with water and extracted twice with dich[oromethane. The combined organic extracts were washed with brine and dried (sodium carbonate). After evaporation of the so[vent the residue was purified by chromatography(si[icage[, e[uents: ethy[ acetate hexane) yie[ding 1.80 g (33.3%) of the tit[e compound.UPLC-MS: RT = 1.23 mm; mz = 292 4 (ES+, M+1)

The synthetic route of 128071-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; GOLZ, Stefan; TELSER, Joachim; REHWINKEL, Hartmut; SIEBENEICHER, Holger; BUCHMANN, Bernd; ZORN, Ludwig; EIS, Knut; KOPPITZ, Marcus; LINDNER, Niels; HEROULT, Melanie; NEUHAUS, Roland; WO2013/182612; (2013); 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.39998-25-9, name is Methyl 2-(pyridin-3-yl)acetate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 2-(pyridin-3-yl)acetate

To a solution of methyl 2-(pyridin-3-yl)acetate (15.1 g, 100 mmol, 1 equiv) in anhydrous THF (180 mL) was added LiAlH4 (4.l8 g, 110 mmol, 1.1 equiv) in portions at 0C. The reaction mixture was stirred at 0C for 1 hour. Then the reaction was quenched carefully with 10% NaOH (aq.), filtered, and extracted with DCM (3 * 150 mL). The combined organic phase were washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo to afford the title compound 2-(pyri din-3 -yl)ethanol as a yellow oil (6.1 g, 51% yield). LC-MS: m/z 124.1 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39998-25-9, Methyl 2-(pyridin-3-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem