Tag: M.W:200-300

Electric Literature of 127446-34-8 ,Some common heterocyclic compound, 127446-34-8, molecular formula is C11H13ClN2O2, 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.i. 7-chloro-3-fluoro-1,8-naphthyridin-2(1H)-one To a solution of N-(6-chloro-3-formylpyridin-2-yl)pivalamide (prepared as described in J. Org. Chem. (1990), 55, 4744; 3.0 g, 12.64 mmol) in MeCN (250 mL) was added triethyl 2-fluoro-phosphonoacetate (4 g, 16.51 mmol), lithium chloride (0.935 g) and DBU (2.8 mL, 18.7 mmol). The mixture was stirred at rt for 4 h. The solvent was evaporated and the residue was partitioned between 1N HCl (100 mL) and ether (150 mL). The aq. layer was extracted with ether (100 mL) and the combined ethereal layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was taken up in dioxane (15 mL) and 6N HCl (50 mL) was added. The mixture was heated to reflux for 90 min. The mixture was cooled to 0 C. and the volatiles were removed in vacuo. The solids were filtered off and washed with water. The solid was dried in vacuo to afford the title compound as a yellow solid (1.38 g, 56% yield). The title compound was only 70% pure. MS (ESI, m/z): 199.1 [M+H+] for C8H4N2OClF.

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. 127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2012/40989; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 880870-13-3, Adding some certain compound to certain chemical reactions, such as: 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine,molecular formula is C6H5BrClNO, 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 880870-13-3.

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged nitrogen for 15 min. Next, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95C for 12 h under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0 – 30% ethyl acetate/hexanes to afford the product. 1HNMR (500 MHz, DMSO- 6) delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS: [(M+l)]+ = 169.

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1093879-46-9 , The common heterocyclic compound, 1093879-46-9, name is 2-(6-Bromopyridin-2-yl)acetic acid, molecular formula is C7H6BrNO2, 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.

Step 1 : to a solution of 2-(6-bromopyridin-2-yl)acetic acid (266 mg, 1 .23 mmol) in DMF (5 ml.) were added DMAP (150 mg, 1.23 mmol), EDCl.HCl (279 mg, 1 .35 mmol) and [4-methyl- 2-(piperidin-1 -yl)phenyl](5-methylfuran-2-yl)methanamine Ex.2 (350 mg, 1.23 mmol). The reaction mixture was stirred at rt. After completion of the reaction (monitored by TLC), sat. NH4CI was added and the solution was extracted with EtOAc. The organic layer was washed with sat. NH4CI, dried over MgS04, filtered and evaporated to dryness under reduced pressure. The crude material was purified by column chromatography on silica gel using Cyclohexane/EtOAc (70:30) as eluent to afford 2-(6-bromopyridin-2-yl)-N-{[4-methyl-2- (piperidin-1 -yl)phenyl](5-methylfuran-2-yl)methyl}acetamide (470 mg, 79%) as yellow oil. 1H NMR (300 MHz, DMSO-d6, d in ppm): 1.39-1 .59 (m, 6H), 2.17 (s, 3H), 2.26 (s, 3H), 2.52- 2.63 (m, 2H), 2.73-2.87 (m, 2H), 3.66 (s, 2H), 5.91 (d, 1 H, J=3.3Hz), 5.94 (dd, 1 H, J=3.0Hz, J=0.9Hz), 6.49 (d, 1 H, J=8.4Hz), 6.91 (d, 1 H, J=7.9Hz), 6.95 (s, 1 H), 7.20 (d, 1 H, J=7.8Hz), 7.35 (dd, 1 H, J=7.5Hz, J=0.6Hz), 7.49 (dd, 1 H, J=7.9Hz, J=0.7Hz), 7.68 (t, 1 H, J=7.4Hz), 8.86 (d, 1 H, J=8.4Hz).

The synthetic route of 1093879-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (76 pag.)WO2018/138356; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 112006-57-2, 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. 112006-57-2, name is 2-(Benzylthio)-N,N-dimethylnicotinamide. A new synthetic method of this compound is introduced below.

EXAMPLE 2 N,N-Dimethyl-2-aminosulfonyl-3-pyridinecarboxamide A mixture of 4.4 ml of concentrated hydrochloric acid, 66 ml of methylene chloride, 34 ml of water and 4.0 g (14.7 mmol) of the N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was cooled to 0 C. Maintaining a temperature of -5 to 3 C., 60 ml (40.5 mmol) of 5% sodium hypochlorite was added dropwise over 15 minutes. The resulting yellow emulsion was stirred at 0 C. an additional 20 minutes. The reaction mixture was then poured into water and extracted with methylene chloride. The combined organic extracts were kept at 0 C. and washed with a saturated sodium bisulfite solution and dried over sodium sulfate. After 30 minutes, the yellow solution was filtered into a reaction flask and cooled to -78 C. and 5 ml (431 mmol) of dry ammonia added. The reaction mixture was allowed to warm to room temperature and the solvent removed under reduced pressure. The resulting solid was slurried with 5 ml of water and the insoluble white solid collected by filtration to provide 2.0 g of the subject compound, m.p. 198-209 C.(d). NMR (DMSO): delta 2.70 (s, 3H, NCH3); 2.93 (s, 3H, NCH3); 7.60-7.75 (m, 1H); 7.90 (m, 1H); and 8.75 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112006-57-2, 2-(Benzylthio)-N,N-dimethylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4789393; (1988); A;,
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

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

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

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

Related Products of 62150-46-3, 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 62150-46-3, name is 4-Bromopicolinamide. This compound has unique chemical properties. The synthetic route is as follows.

The flask was charged with (2-(2-chlorophenyl)-8-methylquinolin-3-yl)methan- amine (100.0 mg, 0.354 mmol), obtained from A-1216 US PSP, procedure D, 4- bromopicolinamide (92 mg, 0.460 mmol), diisopropylethylamine (0.080 ml, 0.460 mmol) and 1-butanol (2.0 ml ) and sealed. The mixture was subjected to microwave at 180C for 4hrs. After cooled to room temperature, the mixture was concentrated, and the residue was diluted with MeOH. The solution was purified by HPLC, 25%-45% of B in 35min. The collected fractions were concentrated and dissolved in CH2Cl2, neutralized by washing with aq. NaHCO3. The CH2Cl2 layer was dried, concentrated and gave 4-((2-(2-chlorophenyl)-8-methylquinolin- 3-yl)methylamino)picolinamide, 1H-NMR (MeOD) delta 8.21 (s, 1 H), 8.01(d, J= 5.6 Hz, IH), 7.71 (d, J= 8.0 Hz, IH), 7.41-7.62 (m, 6 H), 7.20 (d, J= 2.4 Hz, IH), 6.50 (dd, J= 5.6,2.4 Hz, IH) 4.42 (d, J= 11.0 Hz, IH), 4.27 (d, J= 11.0 Hz, IH), 2.73 (s, 1 H). Mass Spectrum (ESI) m/e = 403.1 (M + 1).

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 62150-46-3, 4-Bromopicolinamide.

Reference:
Patent; AMGEN INC.; WO2008/118455; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 124236-37-9 ,Some common heterocyclic compound, 124236-37-9, molecular formula is C8H6F3NO2, 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.

Intermediate A-28A: tert-Butyl (2-methoxy-6-(5-(trifluoromethyl)picolinoyl)phenyl)carbamate [0346] tert-butyl 2-methoxyphenylcarbamate (443.3 mg, 1.986 mmol) in ether (5 mL) under N2 was added t-BuLi (2.6 mL, 4.42 mmol). The reaction mixture was stirred for 2 h, and then cooled to -78 C. To the reaction mixture was added a solution of methyl 5-(trifluoromethyl)picolinate (501.3 mg, 2.44 mmol) in ether (10 mL) dropwise via cannula over 5 min. After 2 h, the reaction mixture was warmed to room temperature, stirred for an additional hour, and then the reaction was quenched by the addition of water with vigorous stirring. The reaction mixture was diluted with EtOAc, the organic phase was separated, washed with sat NaCl then dried (Na2SO4), filtered and concentrated to yield a yellow solid. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, 0% to 100% solvent A/B=hexane/EtOAc, REDISEP SiO2 40 g) to obtained Intermediate A-28A (546.8 mg, 69.5% yield)) as a yellow solid: 1H NMR (400 MHz, chloroform-d) delta ppm 8.83-8.88 (1H, m), 8.24 (1H, d, J=8.4Hz), 8.07 (1H, dd, J=8.4, 1.8 Hz), 7.25 (1H, d, J=1.5 Hz), 7.18-7.24 (1H, m), 7.09 (1H, dd, J=8.0, 1.7 Hz), 6.95 (1H, s), 3.93 (3H, s), 1.25 (9H, s).

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. 124236-37-9, Methyl 5-(trifluoromethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gavai, Ashvinikumar V.; DeLucca, George V.; O’Malley, Daniel; Gill, Patrice; Quesnelle, Claude A.; Fink, Brian E.; Zhao, Yufen; Lee, Francis Y.; US2014/87992; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem