Tag: M.W:200-300

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 1060814-91-6, name is Ethyl 2-(4-bromopyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows. name: Ethyl 2-(4-bromopyridin-2-yl)acetate

To a solution of compound 2-7 (1.3 g, 5.33 mmol, 1 eq) in dimethylformamide (2 mL) was added sodium hydride (533 mg, 13.32 mmol, 60% purity in mineral oil, 2.5 eq) at 0C under nitrogen atmosphere. The mixture was stirred at 0C for 20 minutes and methyl iodide (3.78 g, 26.63 mmol, 1.66 mL, 5 eq) was added. The mixture was stirred at 20C for 10 minutes. TLC (petroleum ether: ethyl acetate = 5:1) indicated the starting material was consumed completely and a new spot was formed. The mixture was poured into water (10 mL) and 1N hydrochloric acid (4 mL). The mixture was adjusted to pH = 8 with sodium bicarbonate solid and extracted with ethyl acetate (20 mLx3). The combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford compound 2-21 (1.44 g, 4.90 mmol, 91.92% yield) as yellow oil. LCMS: RT = 1.408 min, purity: 92.52 %, m/z 271.9,273.9 [M+H]+.1H NMR (CDCl3, 400 MHz): d 8.38 (d, J = 7.2 Hz, 1H), 7.48 (d, J = 2.0 Hz, 1H), 7.34 (dd, J1 = 7.2 Hz, J2 = 2.4 Hz, 1H), 4.17 (q, J = 9.6 Hz, 2H), 1.61 (s, 6H), 1.21 (t, J = 9.2 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1060814-91-6.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201187-18-9, 6-Chloro-4-(trifluoromethyl)nicotinonitrile, 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, Recommanded Product: 6-Chloro-4-(trifluoromethyl)nicotinonitrile, blongs to pyridine-derivatives compound. Recommanded Product: 6-Chloro-4-(trifluoromethyl)nicotinonitrile

General procedure: To a stirred solution of 1Hpyrazole4carbaldehyde (1.00 g, 10.40 mmol) and 6bromo4methylnicotinonitrile (2.05 g, 10.40 mmol) in dioxane (15 mL) were added K2CO3 (4.31 g, 31.20 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes then copper (I) iodide (0.59 g, 3.12 mmol) was added, followed by transN,N’dimethylcyclohexane1,2diamine (2.59 mL, 16.4 mmol). The resulting mixture was degassed again for 10 minutes and heated at 110 C for 1 h under microwave irradiation. The reaction mixture was cooled to ambient temperature, filtered through Celite and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2040% EtOAc/ nhexane) to obtain Intermediate 6 (1.15 g, 52.10%) as pale yellow solid. 1H NMR (300 MHz, DMSOd6) G^ppm 2.62 (s, 3 H), 8.10 (s, 1 H), 8.38 (s, 1 H), 8.95 (s, 1 H), 9.37 (s, 1 H), 9.98 (s, 1 H). LCMS (methodD), retention time 1.68 min, [M+H] 213.2.

The synthetic route of 1201187-18-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64064-71-7, 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. 64064-71-7, name is 6-Bromo-3-nitroimidazo[1,2-a]pyridine, molecular formula is C7H4BrN3O2, 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.

C. 3-Nitro-6-(2-pyridylthio) imidazo [1,2-a] pyridine A solution of 1.61 g. (0.012 mole) of the sodium salt of 2-mercapto pyridine and 2.42 g. (0.01 mole) of 6-bromo-3-nitroimidazo [1,2-a] pyridine in 10 ml. N-methylpyrolidinone is heated at 150 C for 40 minutes under a nitrogen atmosphere. The cooled solution is poured onto 100 ml. of ice-water and the resultant suspension is extracted with ethyl acetate. The combined extracts are washed with saturated aqueous sodium chloride and dried over magnesium sulfate. Evaporation of the solvent to a small volume and dilution with N-hexane yields crystalline material. The solids are purified by chromatography on silica gel. Elution with methylene chloride yields pure 3-nitro 6-(2-pyridylthio) imidazo [1,2-a] pyridine.

According to the analysis of related databases, 64064-71-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US4105767; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89978-52-9, Ethyl 2-bromoisonicotinate, 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, 89978-52-9, blongs to pyridine-derivatives compound. Application In Synthesis of Ethyl 2-bromoisonicotinate

A mixture of 1H-indole-3-carbonitrile (0.1 g), 2-bromoisonicotinic acid ethyl ester (0.16 g), potassium phosphate (0.27 g), (1R,2R)-(-)-N,N’-dimethylcyclohexane-1,2-diamine (0.017 g), copper iodide (0.006 g) and toluene (0.7 mL) was stirred at 110C for 38 hours. The insoluble material was removed by filtration, and this filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane = 10/90 to 66/34) to give the title compound (0.061 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89978-52-9, its application will become more common.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2133332; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 639091-75-1 ,Some common heterocyclic compound, 639091-75-1, molecular formula is C12H16N2O4, 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.

Compound 2E (2.5 g, 9.91 mmol, 1.00 equiv) and CaC12 (1.65 g) were dissolved in EtOH (30 mL). The solution was cooled to 0C then NaBH4 (1.13 g, 29.87 mmol, 3.01 equiv) was gradually added. The solution was left under agitation overnight atambient temperature then the reaction was halted with the addition of water (50 mL). The mixture was extracted three times with 20 mL of EtOAc. The organic phases were combined, washed twice with 20 mL of NaC1 (sat.) then dried over sodium sulfate, filtered and concentrated under reduced pressure to yield 2.0 g (90 %) of compound 2F in the form of a colourless solid.

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. 639091-75-1, Methyl 2-(Boc-amino)isonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 823221-93-8, 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.823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, molecular weight is 260.44, as common compound, the synthetic route is as follows.

Prepared using General Procedure 17: To a stirred a solution of 5- bromo-2-chloro-4-(trifluoromethyl)pyridine (150 mg, 0.576 mmol) in acetonitrile (2 mL) was added sodium iodide (518 mg, 3.45 mmol). The reaction mixture was heated to 40C and acetyl chloride (26.0 mg, 0.345 mmol) was added. The reaction mixture was stirred at 40C for 90 min. Once cooled, the reaction was quenched with NaHC03 (5 mL) and extracted with EA (3 x 5 mL). The combined organics were washed with brine (10 mL), dried over MgS04 and concentrated to give 80.0 mg (40%) of 5-bromo- 2-iodo-4-(trifluoromethyl)pyridine as a white crystalline solid which was used in the subsequent step without purification. LCMS-ESI (m/z) calculated for C6H2BrF3IN: 351.9; found 352.5 [M+H]+, tR = 3.91 min. (Method 1).

Statistics shows that 823221-93-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; RECEPTOS, INC.; BOEHM, Marcus, F.; MARTINBOROUGH, Esther; MOORJANI, Manisha; TAMIYA, Junko; HUANG, Liming; YEAGER, Adam, R.; BRAHMACHARY, Enugurthi; FOWLER, Thomas; NOVAK, Andrew; MEGHANI, Premji; KNAGGS, Michael; WO2013/90454; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886371-28-4, 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. 886371-28-4, name is 3-Bromo-6-chloroimidazo[1,2-a]pyridine, molecular formula is C7H4BrClN2, 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.

General procedure: To an oven dried 5 mL microwave vessel was addedPd(dppf)Cl2·CH2Cl2 (4 mol%), halide/pseudohalide (1 equiv),boron coupling partner (1 equiv), and Cs2CO3 (3 equiv). Thevessel was then capped and purged with N2 before addition ofCyrene (1 mL, 0.25 M) and H2O (1.8 mL). The reaction mixturewas heated to 50 C and maintained at this temperature withstirring for 5 h before the vessel was vented and decapped. Thesolution was then diluted with Et2O (10 mL) and washed withwater (2 × 20 mL) and brine (2 × 20 mL). The organics were thenpassed through a hydrophobic frit and concentrated underreduced pressure to give a residue, which was purified by flashchromatography (silica gel) to afford the title compound.

According to the analysis of related databases, 886371-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wilson, Kirsty L.; Murray, Jane; Jamieson, Craig; Watson, Allan J. B.; Synlett; vol. 29; 5; (2018); p. 650 – 654;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, 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, COA of Formula: C12H8ClNO, blongs to pyridine-derivatives compound. COA of Formula: C12H8ClNO

4-chlorophenylpyridyl ketone (43.5mg, 0.2mmol), dibromantin (57.2mg, 0.2mmol) and Pd (OAc) 2 (4.5mg, 0.02mmol), 2mL of dichloroethane, 90C The reaction was carried out for 12 hours and purified by thin layer chromatography to obtain 30.2 mg of 2-bromo-4-chlorophenylpyridylmethanone, with a yield of 50.9%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, and friends who are interested can also refer to it.

Reference:
Patent; China Three Gorges University; Liu Qixing; Chen Yongsheng; Zhang Yin; Chen Danyi; Wen Simiaomiao; Zhao Rongrong; Liu Yiheng; Zhou Haifeng; (14 pag.)CN110563641; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

To a vial were added 2,6-dibromo-4-methylpyridine (121 mg, 0.482 mmol), cw-butyl 4- [l-hydroxy-l-(l,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate (75 mg, 0.241 mmol), potassium carbonate (100 mg, 0.722 mmol), pivalic acid (5.59 mu, 0.048 mmol),tetrakis(triphenylphosphine)palladium(0) (11.1 mg, 9.63 mu?iotaomicronGamma) and N,N-dimethylacetamide (760 mu). The vial was sealed and placed under argon through 3 cycles of evacuation and argon flushing then reacted at 80 C overnight. The resulting mixture was cooled, diluted with ethyl acetate, filtered through a plug of CELITE and concentrated. The residue was purified by column chromatography on silica gel (0-100% ethyl acetate/hexanes) to afford racemic-cw-butyl 4- { 1 -[5-(6-bromo-4-methylpyridin-2-yl)- 1 ,3 -thiazol-2-yl]- 1 -hydroxyethyl } – cyclohexanecarboxylate.Two enantiomers were separated by chiral super critical fluid chromatography (ChiralTechnology IC-H, 2.1 x 25 cm, 5 uM, 70/30 ethanol/C02, Flow Rate: 70 mL/min, 8 min run time, WL: 220 nm). Elution was observed at 5.20 min and 6.08 min. Pooled fractions of each peak were concentrated under reduced pressure.Enantiomer 1 (retention time 5.20 min): MS ESI calc’d. for C22H29BrF3N203S [M + H+] 481 and 483, found 481 and 483.Enantiomer 2 (retention time 6.08 min): MS ESI calc’d. for C22H29BrF3N203S [M + H+] 481 and 483, found 481 and 483.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73112-16-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; DI FRANCESCO, Maria Emilia; HAIDLE, Andrew, M.; OTTE, Ryan, D.; ELLIS, John Michael; CHILDERS, Kaleen Konrad; NORTHRUP, Alan, B.; YANG, Liping; WO2012/154520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 727356-19-6, 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.727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

Step 3; Preparation of trans-4-{[5-(6-bromopyridin-2-yl)thiazol-2-ylamino]methyl}cyclohexanecarboxylic acid methyl ester A solution of trans-4-thiouredide methylcyclohexane carboxylic acid methyl ester (1.55 g, 6.73 mmol) obtained in Step 2,2-bromo-6-chloromethylpyridine (1.38 g, 6.73 mmol) obtained in Step 1 of Example 1 in ethanol (15 ml) was stirred under refluxing for 4 hours. After the reaction solution was cooled to room temperature, N,N-dimethylformamide dimethylacetal (0.9 ml, 10 mmol), triethylamine (1.8 ml, 20 mmol) were added and the mixture was stirred under refluxing for 1 hour. The reaction solution was cooled to room temperature and the solid obtained by vacuum concentration was collected by filtration. trans-4-{[5-(6-bromopyridin-2-yl)thiazol-2-ylamino]methyl}cyclohexanecarboxylic acid methyl ester (2.02 g, 73%) was obtained by sequentially washing with water (10 ml), diethyl ether (10 ml) and drying in vacuo. 1H-NMR (400 MHz, DMSO-d6) delta: 8.15(1H,t,J=5.7 Hz), 7.83(1H,s), 7.74(1H,d,J=7.9 Hz), 7.63(1H,t,J=7.9 Hz), 7.31(1H,d,J=7.9 Hz), 3.15-3.06(2H,m), 2.32-2.19(1H,m), 1.97-1.87(2H,m), 1.85-1.76(2H,m), 1.63-1.49(1H,m), 1.37-1.23(2H,m), 1.06-0.93(2H,m).

The chemical industry reduces the impact on the environment during synthesis 727356-19-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JAPAN TOBACCO INC.; US2006/205731; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem