Month: April 2022

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

Reference of 54453-93-9 , The common heterocyclic compound, 54453-93-9, name is Ethyl 2-Chloropyridine-4-carboxylate, molecular formula is C8H8ClNO2, 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: For the synthesis of substituted benzoylhydrazines, a mixture of corresponding esters (20 mmol), 85% hydrazine hydrate (20 mmol) in ethanol (35 ml) was heated to reflux for 5 h. After that, the solution was poured into ice-water. The precipitate was filtered and crystallized from ethanol.

The synthetic route of 54453-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Kai; Lu, Xiang; Zhang, Hong-Jia; Sun, Juan; Zhu, Hai-Liang; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 473 – 478;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 94220-38-9, 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 94220-38-9, name is 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]-pyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1 7-(4-Cyanoanilino)-5-methyl-1H-pyrazolo[4,3-b]pyridine (E1) STR14 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (4 g, 0.024 mole) was heated at reflux under nitrogen with 4-aminobenzonitrile (9.44 g, 0.08 mole) in dry xylene (25 ml) for 8 h. The resulting yellow crystalline solid was collected and washed repeatedly with ethyl acetate. This solid was recrystallized from methanol/ethyl acetate to give yellow needles (2.96 g, 43%) of the required product as its hydrochloride salt. A sample of this material (500 mg) was neutralised by dissolving with warming in the minimum volume of water/methanol and adding sufficient 10% sodium hydroxide to give a pH of 8. The resulting flocculant precipitate was collected, washed with water and dried to give a pale yellow solid (408 mg, 94%) which was recrystallized from ethyl acetate/methanol to give the title compound as the free base, m.p. 280-282 C. (decomposition). (Found: C, 66.13; H, 4.28; N, 27.81. C14 H11 N5.0.25H2 O requires C, 66.26; H, 4.57; N, 27.59%).

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 94220-38-9, 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]-pyridine.

Reference:
Patent; Beecham Group p.l.c.; US4576952; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 709652-82-4, Adding some certain compound to certain chemical reactions, such as: 709652-82-4, name is 2-Amino-5-bromonicotinonitrile,molecular formula is C6H4BrN3, 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 709652-82-4.

1.2 e-Amino-S-cyano-S’.e’-dihydro^’H-tS^’jbipyridinyM ‘-carboxylic acid tert- butyl ester To a solution of 2-amino-5-bromo-nicotinonitrile (0.60 g; 3.02 mmol) in dioxane (24 mL) and water (6 mL) 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan- 2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.04 g; 3.32 mmol) and Na2CO3 (0.98 g; 9.05 mmol) were added and the mixture was degassed for 30 min. 1 ,1’-Bis(diphenylphosphino)ferrocene]dichloro- palladium(ll) complex with dichloromethane (0.13 g; 0.15 mmol) was added and the reaction mixture was heated to 90 C for 10 h. The reaction mixture was cooled to ambient temperature, filtered through celite and the solvent was concentrated under reduced pressure. The residue was purified by flash column chromatography using petrol ether and ethyl acetate (5:5) to afford the title compound (450.0 mg; 50%) as a pale-yellow solid; 1H NMR (400 MHz, DMSO-d6) delta 8.32 (d, J = 2.5 Hz, 1H), 7.92 (d, J = 2.5 Hz, 1H), 6.92 (s, 2H), 6.08 (s, 1H), 3.94 (s, 2H), 3.49 (t, J = 5.6 Hz, 2H), 2.37 (d, J = 1.5 Hz, 2H), 1.40 (s, 9H); LC/MS (B), Rt: 3.50 min; (M+H) 301.2.

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. 709652-82-4, 2-Amino-5-bromonicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; DORSCH, Dieter; BUCHSTALLER, Hans-Peter; WO2015/14442; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 944317-27-5, 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. 944317-27-5, name is 6-Bromo-3-chloro-2-methylpyridine. A new synthetic method of this compound is introduced below.

6-Bromo-3-chloro-2-methylpyridine (1.07 g), Pd(dppf)Cl2 DCM (423 mg) and triethylamine (524 mg) were stirred in a mixed solution of methanol (7.5 mL) and DMF (7.5 mL) in the presence of carbon monoxide (3 atm) at 90C for 3 hr. The solvent of the reaction mixture was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (724 mg). MS (ESI+) : [M+H]+185.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944317-27-5, 6-Bromo-3-chloro-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem