Month: April 2022

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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid. A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoro-4-iodonicotinic acid

To a solution of the product from step 2 (23.5 g, 88 mrnoi) in methanol (300 mL) was added dropwise TMSCHN2 (220 mL, 440 minol) at 05C under N2 . After addition was complete, the mixture was stirred at RT for 16 hrs, water was added and the mixture extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The crude product was purified bychromatography on silica (10% EtOAc in petroleum ether) to give the title compound as an oil. LRMS m/z M+H) 282.1 found, 282.1 required.

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, 884494-51-3, 2-Fluoro-4-iodonicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); 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. 20511-15-3, name is 3-Amino-4-chloropyridine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H5ClN2

[Example 719] Compound q1 4-Chloropyridine-3-carbonitrile [1519] aqueous tetrafluoroboric acid solution (10 ml) was added to a solution of 4-chloropyridin-3-amine (1.29 g, 10.0 mmol) in ethanol (10 ml) at 0C. An aqueous solution (10 ml) of sodium nitrite (725 mg, 10.5 mmol) was added to the resultant mixed solution at the same temperature, and it was stirred at the same temperature for 30 minutes. The precipitate was collected by filtration and washed with ethanol, and the resultant brown solid (1.94 g) was then dissolved in acetonitrile (10 ml). A mixed solution of sodium cyanide (980 mg, 20.0 mmol) and copper(I) cyanide (896 mg, 10.0 mmol) in water (10 ml) and acetonitrile (1 ml) was added to the resultant solution at 0C, and it was stirred while gradually warming to room temperature for 10 hours. The reaction mixture was cooled to 0C, after which a saturated aqueous solution of sodium bicarbonate was added, and it was stirred for five minutes. The resultant solution was extracted with ethyl acetate, and the organic layer was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (605 mg, 44%) as a pale yellow solid. 1H-NMR (300 MHz, CDCl3) delta: 8.87 (1H, s), 8.72 (1H, d, J = 3.9 Hz), 7.51 (1H, d, J = 3.9 Hz).

The synthetic route of 20511-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; MURATA, Takeshi; NIIZUMA, Satoshi; HARA, Sousuke; KAWADA, Hatsuo; HADA, Kihito; SHIMADA, Hideaki; TANAKA, Hiroshi; NAKANISHI, Yoshito; EP2842939; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1142363-52-7, name is JNJ-40346527. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1142363-52-7

Example 23 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide hydrochloride salt A solution of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (49.2 mg, 0.107 mmol, as prepared in Example 15, step (h)) in EtOH (2 mL) was treated with HCl (26.6 muL, 0. 107 mmol, 4 M in dioxane) at room temperature for 1.5 h. The solvents were evaporated in vacuo, and the residue was dried under high vacuum overnight. The solid was dissolved in a minimum amount of EtOH (900 muL) with sonication and heating. While warm, the solution was slowly treated with hexanes (3 mL) to the cloud point. The mixture was heated again until clear, the sides of the vial were scratched, and the mixture was allowed to cool. The solid was filtered and air-dried to afford the title compound (20mg, 38%) as white crystals. 1H-NMR (CD3OD; 400 MHz): delta 9.17 (d, 1H, J=8.4 Hz), 8.10 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 6.38-6.32 (m, 1H), 3.76-3.65 (m, 1H), 2.54-2.46 (m, 2H), 2.25-2.19 (m, 2H), 1.98-1.91 (m, 2H), 1.76-1.65 (m, 4H), 1.43 (s, 6H), 1.30 (s, 6H), 1.15 (s, 6H). Mass spectrum (APCI, m/z): Calcd. for C27H35N5O2, 462.3 (M+H), found 462.3.

With the rapid development of chemical substances, we look forward to future research findings about 1142363-52-7.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (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. 944900-06-5, name is 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, the common compound, a new synthetic route is introduced below. Product Details of 944900-06-5

2-Chloro-6-(trifluoromethyl)nicotinaldehyde (176 mg, 0.840 mmol), cyclopropylboronic acid (152 mg, 1.76 mmol), sodium carbonate (267 mg, 2.52 mmol) and tetrakis(triphenylphosphine)palladium (0) (48.5 mg, 0.0420 mmol) were combined, diluted with toluene (2 mL) and water (200 muL). The reaction vial was purged with argon, heated to 900C and stirred for 24 hours. The reaction was allowed to cool, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 2-cyclopropyl-6- (trifluoromethyl)nicotinaldehyde (130 mg, 0.604 mmol, 71.9 % yield).

The synthetic route of 944900-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); 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. 436799-32-5, name is 5-Bromo-2-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrF3N

In a dried 250 mL 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (16 mL, Aldrich, inhibitor free) followed by N, N-diisopropylamine (0.895 g, 8.85 mmol, Aldrich, redistilled 99.95% pure). After cooling the stirred solution to -70 0C, n-butyl lithium (3.54 mL of a 2.5M solution in hexanes, 8.85 mmol) was added dropwise, keeping the reaction temperature less than -60 0C. The resulting solution was stirred at -70 0C for a further 10 min, then warmed to -20 0C, before immediately cooling to -90 0C. A solution of 5-bromo-2-(trifluoromethyl)pyridine (2 g, 8.85 mmol) in anhydrous THF (8 ml_, Aldrich, inhibitor free) was added dropwise, keeping the reaction temperature less than -85 0C. The resulting orange solution was stirred at -90 0C for 40 min.In a separate dried 250 ml_ 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (5 ml_, Aldrich, inhibitor free) followed by methyl iodide (5 ml_, 80 mmol). The solution was cooled to -90 0C. To this was added (via cannula) the solution of the pre-formed lithiated pyridine, controlling the rate so as to keep the reaction temperature of the receiving flask less than -80 0C. The resulting dark solution was stirred at -90 0C for a further 15 min (LCMS indicated reaction complete). The reaction was quenched with sat aq. NH4CI solution (50 mL), then allowed to slowly warm to rt. Organics were extracted with EtOAc (2 x 50 mL), then the combined organic layers washed with water (50 mL), then brine (50 mL), separated, dried over MgSO4, and then filtered. Concentration in vacuo gave 1.68 g of a brown oil which was purified via short-path vacuum distillation (45-46 0C, ca. 5 mmHg) to give 5-bromo-4-methyl-2- (trifluoromethyl)pyridine 1-2 (0.289 g, 14%) as a yellow oil (>97% pure). MS (M + H)+: 241.8, tR = 2.458 min (method 1); 1H NMR (CDCI3) delta 8.74 (1H, s), 7.56 (1H, s), 2.50 (3H, s).

The synthetic route of 436799-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 405224-23-9, 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. 405224-23-9, name is 5-Bromo-2-chloronicotinonitrile. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-2-chloronicotinonitrile (1.0 equiv.) in THF and water (4:1, 0.2M) was added potassium carbonate (3.0 equiv.) and 4-methyl-3-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)aniline (1.0 equiv.) and the solution was degassed with Argon. PdCl2(dppf)-DCM (0.1 equiv.) was added and the solution was refluxed at 90 C for 24 hours. Upon cooling to room temperature, the reaction was partitioned between 1:1 EtOAc/n- heptanes and H2O, mixed, separated, washed with NaCl (sat.) , dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography (0-80% EtOAc/n-heptanes) to yield 5-(5-amino-2-methylphenyl)-2-chloronicotinonitrile in 82% yield. LCMS (m/z) (M+H) = 243.9, Rt = 0.56 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,405224-23-9, its application will become more common.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, 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, SDS of cas: 850663-54-6, blongs to pyridine-derivatives compound. SDS of cas: 850663-54-6

A mixture of 4-chloro-2-hydroxy-5-nitropyridine (3.00 g, 17.2 mmol), phenylboronic acid (2.51 g, 20.6 mmol), PdC12(dppf)-CH2Cl2adduct (1.40 g, 1.72 mmol), and potassium carbonate (4.75 g, 34.4 mmol) in THF (100 mL) was heated at 85 C for 16 h. The product mixture was cooled and partitioned between water and ethyl acetate (3x). The combined organic layers were dried over Na2504, filtered and concentrated. The residue was purified by flash column chromatography (5i02 cartridge), eluting withMeOH/CH2C12 (0-10%) to afford the title compound. MS: m/z = 217 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 92992-85-3, Adding some certain compound to certain chemical reactions, such as: 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine,molecular formula is C7H8BrN, 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 92992-85-3.

To a mixture of 2-methylpiperazine-1-carboxylic acid tert-butyl ester (2 g),2-bromo-3,5-dimethylpyridine (1.95 g),tris(dibenzylideneacetone)dipalladium(0)(183 mg),rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (250 mg) and tert-butoxy sodium (1.3 g) was added toluene (33 mL) and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled and filtered through celite. The filtrate was evaporated and the obtained residue was purified by column chromatography (hexane:ethyl acetate)to give 4-(3,5-dimethylpyridin-2-yl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (1.61 g). MS(ESI)m/z:206(M+H)+

According to the analysis of related databases, 92992-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3430-18-0, Adding some certain compound to certain chemical reactions, such as: 3430-18-0, name is 2,5-Dibromo-3-methylpyridine,molecular formula is C6H5Br2N, 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 3430-18-0.

[0231] A solutionof2,5-dibromo-3-methylpyridine (1) 3 g,12.1 mmol) in methanol (20 ml) was added sodium methoxide(2M, 20 mL) and refluxed at 100 C. for 2 h. The reactionmixture was poured on ice water and neutralized with aqueoushydrochloric acid (1M) and extracted with dichloromethane(2×15 ml). The combined organic layer waswashed with water, brine, dried over sodium sulfate, andconcentrated at reduced pressure to give 5-Bromo-2-methoxy-3-methyl-pyridine (35), which was used without furtherpurification (1.9 g, 77.8%).

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. 3430-18-0, 2,5-Dibromo-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Naik, Maruti N.; PEER MOHAMED, Shahul Hameed; Shandil, Radha K.; Shinde, Vikas Narayan; Shirude, Pravin S.; Chatterji, Monalisa; US2015/25087; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79055-59-7, 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 79055-59-7, name is 2-Bromo-6-methylpyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Ethyl 4-[[(lR)-2,2-difluoro-l-methyl-propyl]sulfamoyl]-3-fluoro-l -methyl-pyrrole -2- carboxylate (250 mg, 0.73 mmol) and 2-bromo-6-methylpyridin-4-amine (163.91 mg, (0748) 0.88 mmol) in THF (3.91 mL, 0.89 g/mL, 48.32 mmol) was stirred at room temperature and then lithium bis(trimethylsilyl)amide in THF (2.19 mL, 1 M, 2.19 mmol) was added at once. (0749) The mixture was stirred for 1 hour and then quenched with NH4CI and extracted with EtOAc. The combined extracts were concentrated and the obtained crude was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0: 100). The desired fractions were concentrated in vacuo and the obtained oil was crystallised out of iPrOH. The crystals were collected and dried in a vacuum oven at 55C yielding compound 157 (252 mg) of compound 157 as a white powder. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.07 (d, J=7.0 Hz, 3 H), 1.57 (t, J=19.1 Hz, 3 H), 2.41 (s, 3 H), 3.47 – 3.64 (m, 1 H), 3.80 (s, 3 H), 7.49 – 7.53 (m, 1 H), 7.55 (d, J=4.4 Hz, 1 H), 7.77 (br. s, 1 H), 8.22 (br. s., 1 H), 10.44 (br. s., 1 H). Method B: Rt: 1.00 min. m/z: 483.0 (M-H)~ Exact mass: 484.0.

According to the analysis of related databases, 79055-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem