Day: April 11, 2022

Reference of 135450-23-6 , The common heterocyclic compound, 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, molecular formula is C7H5ClN2, 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.

A solution of 1-(1-methyl-1 /-/-tetrazol-5-yl)-1,3-dihydro-2H-benzo[d]imidazole-2-thione H (26 mg, 0.1 1 mmol) in dry DMF (1 mL) was treated with a solution of A/-(6-(bromomethyl)pyridin- 2-yl)-2,2-difluoro-2-phenoxyacetamide E (49 mg, 0.14 mmol) in dry THF (0.7 mL) and caesium carbonate (60 mg, 0.18 mmol) was added. The mixture was stirred at RT for 100 min then diluted with EtOAc (20 mL), washed with water (3 x 20 mL) and brine, dried (MgSCU) and chromatographed on silica (4 g Puriflash cartridge) eluting with 0-50% EtOAc / PE to give 2,2-difluoro-/V-(6-(((1-(1-methyl-1H-tetrazol-5-yl)-1H-benzo[d]imidazol-2- yl)thio)methyl)pyridin-2-yl)-2-phenoxyacetamide 1 (48 mg, 84%) as a colourless gum. 1H N MR (500 MHz, CDC) delta 8.90 (s, 1H), 8.13 (d, J = 8.3 Hz, 1H), 7.77 (d, J = 8.0 Hz, 1H), 7.74 – 7.68 (m, 1H), 7.45 – 7.33 (m, 3H), 7.32 – 7.26 (m, 5H), 7.07 – 7.00 (m, 1H), 4.67 (s, 2H), 3.92 (s, 3H); LCMS (method B): 3.28 min (509, MH+). Potassium carbonate was used instead of caesium carbonate

The synthetic route of 135450-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDAG CROP PROTECTION LTD; URCH, Christopher, John; BUTLIN, Roger, John; CHRISTOU, Stephania; BOOTH, Rebecca, Kathryn; (111 pag.)WO2018/130838; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 127446-34-8, 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. 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, molecular formula is C11H13ClN2O2, 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.

A mixture of (2R,5R)-2-methyl-5-phenylmorpholine (Preparation 2, 53 g, 300 mmol), N-(6-chloro-3-formylpyridin-2-yl)pivalamide, N,N-dimethylformamide (150 mL) and diisopropylethylamine (53 mL, 300 mmol) was stirred at 100 C. for 18 h. The mixture was cooled to room temperature and concentrated. The residue was dissolved in ethyl acetate (1 L) and water was added (600 mL). The layers were separated. The organic layer was extracted with aqueous hydrochloric acid (1 N, 500 mL), dried over sodium sulfate, filtered and concentrated. The residue was dissolved in dichloromethane and filtered through silica gel, rinsing through with 50% ethyl acetate in heptanes (3 L) followed by 100% ethyl acetate (500 mL) to provide the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.28 (3H, d, J=6.2 Hz), 1.36 (9H, s), 3.04 (1H, dd, J=13.6, 11.0 Hz), 3.75 (1H, m), 4.04 (1H, dd, J=12.0, 3.8 Hz), 4.45 (1H, dd, J=12.1, 1.6 Hz), 6.24 (1H, d, J=9.0 Hz), 7.26 (4H, m), 7.60 (1H, d, J=8.8 Hz), 9.52 (1H, m), 11.58 (1H, br s).

According to the analysis of related databases, 127446-34-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2011/281854; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2369-19-9, 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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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.

Intermediate 8:2-fluoro-5-methylnicotinic acid[00363] A 1.6M solution of butyl lithium in hexanes (28.13 ml, 45 mmol) was added dropwise to a solution of diisopropylamine (6.36 ml, 45 mmol) in tetrahydrofuran (80 ml) keeping the temperature at -78C. After complete addition, the mixture was allowed to warm up to 0C, then stirred at 0C for 10 minutes. The resulting mixture was cooled down to -78C and a solution of 2-fluoro-5-methylpyridine (4.64 ml, 45 mmol) in tetrahydrofuran (15 ml) was added dropwise. The reaction mixture was stirred at -78C for 2 hours then quenched by addition of an excess of CO2 solid. The mixture was allowed to warm up to room temperature. The mixture was acidified with 10% citric acid, diluted with ethyl acetate. The organic layer was collected, washed further with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to leave the desired compound as a white solid (4.9 g, 70% yield).[00364 ] 1H NMR (DMSO-d6, 400 MHz) delta 2.34 (3H, s), 8.20-8.26 (2H, m); MS (ES+) 156, (ES”) 154.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/94992; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 851386-40-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 851386-40-8 as follows.

Under inert gas atmosphere 0.80 g (2.53 mmol) of example XIII.1 , 0.65 g (2.53 mmol) of 2-chloro-4-iodo-3-methyl-pyridine, 1.00 g (10.4 mmol) NaOtBu and 100 mg (0.14 mmol) chloro(2-dicyclohexylphosphino-2’>4′,6′-triisopropyl-1 , 1 ‘-biphenyl)(2-(2- aminoethyl)-phenyl)-palladium (II) are added to 50 mL dioxane and stirred at 45 C over night. Afterwards the solvent is removed, water is added and the product is extracted with EtOAc. The organic layer is dried over MgS04, filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (ACN/H20/TFA). C20H24CIN3O2 (M= 373.9 g/mol) ESI-MS: 374 [M+H]+ Rt (HPLC):0.77 min (method M); The following compounds are prepared analogously to example XXI.1 : For example XXI.3 and XXI.10 the reaction temperature is 70-80 C for 3-4 h. For example XXI.5 the reaction time is 3 h. For example XXI.6 the reaction conditions are 80 C over night,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851386-40-8, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 175204-80-5, 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.175204-80-5, name is 3-Amino-4-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

Example 38 Preparation of 1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-3-(4-(trifluoromethyl)pyridin-3-yl)thiourea (F12) To 4-(trifluoromethyl)pyridin-3-amine (0.091 g, 0.56 mmol) in tetrahydrofuran and under an atmosphere of nitrogen was added sodium hydride (60% in mineral oil, 0.022 g, 0.56 mmol). 3-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (WO 2011/017513) (0.10 g, 0.28 mmol) was added and the reaction was allowed to stir for 48 hours. The reaction mixture was concentrated. Purification by silica gel chromatography provided the title compound (0.024 g, 16%).

Statistics shows that 175204-80-5 is playing an increasingly important role. we look forward to future research findings about 3-Amino-4-(trifluoromethyl)pyridine.

Reference:
Patent; Dow AgroSciences LLC; Baum, Erich W.; Fischer, Lindsey G.; Crouse, Gary D.; Sparks, Thomas C.; Giampietro, Natalie C.; Dent, III, William H.; Niyaz, Noormohamed M.; Petkus, Jeff; Demeter, David A.; Lambert, William Thomas; McLeod, CaSandra L.; Rigsbee, Emily Marie; Renga, James M.; (128 pag.)US2016/21883; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate, molecular formula is C9H10ClNO2, 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.

Phenylboronic acid (3.5 g, 28.7 mmol), ethyl 2-(6-chloropyridin-3-yl)acetate (5.2 g, 26.1 mmol) and tetrakistriphenylphosphine palladium (1.1 g, 0.95 mmol ),was added to a mixture of cyclopentyl methyl ether (80 mL) and 2M sodium carbonate aqueous solution (40 mL), and the mixture was refluxed under a nitrogen gas atmosphere for 15 hours. After cooling to room temperature, deionized water was added, extraction was performed with chloroform, and the solvent was distilled off using a rotary evaporator. The obtained crude product was purified with ethyl acetate (2-(6-phenylpyridin-3-yl)acetate, 3.2 g, 13.3 mmol, 51%) purified by silica gel column chromatography (developing solvent: chloroform).

According to the analysis of related databases, 197376-47-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GUNMA UNIVERSITY; JSR LIFE SCIENCES CORPORATION; JSR CORPORATION; YOSHIHARA, TOSHITADA; TOBITA, SEIJI; ITO, MANABU; MASUDA, NORIO; (44 pag.)JP2018/150245; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 80537-07-1, Adding some certain compound to certain chemical reactions, such as: 80537-07-1, name is 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid,molecular formula is C14H10N2O2, 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 80537-07-1.

EXAMPLE 56 STR64 Thionyl chloride (240 mg) was added dropwise to a stirred mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid [compound (I)] (320 mg) and N,N-dimethylformamide (one drop) in chloroform (10 ml), and then stirred under reflux for 4 hours. After cooling the mixture, chloroform was evaporated in vacuo to give acid chloride of compound (I). Triethylamine (338 mg) was added to a suspension of the acid chloride of compound (I) in methylene chloride (10 ml) under ice-cooling, and to this suspension a solution of 2-ethylpiperidine in methylene chloride was added dropwise. The mixture was stirred under ice-cooling and stood at room temperature overnight. Saturated sodium chloride aqueous solution (20 ml) was added to the mixture and extracted with chloroform (20 ml). The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (8 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-(2-phenylpyrazolo[1,5-a]pyridin-3-ylcarbonyl)-2-ethylpiperidine (263 mg). mp: 182-183 C. IR (Nujol): 1630, 1600, 1520 cm-1 NMR (DMSO-d6, delta): 0.69 (3H, t, J=7.0 Hz), 1.12-1.93 (8H, m), 2.73-3.17 (1H, m), 3.69-4.45 (2H, m) 7.07 (1H, td, J=7.0 Hz and 2.0 Hz), 7.29-8.00 (7H, m), 8.86 (1H, dd, J=7.0 Hz and 1.0 Hz) Analysis Calcd. for C21 H23 N3 O: C 75 65, H 6.95, N 12.60. Found: C 75.75, H 7.01, N 12.66.

According to the analysis of related databases, 80537-07-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4994453; (1991); A;,
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. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-Bromo-2-methoxy-5-methylpyridine

-Bromo-5-bromomethyl-2-methoxy-pyridine To a solution of the product from step 131.4 (3.0 g, 14.7 mmol), was added NBS (3.1 g, 17.6 mmol) and AIBN (121 mg, 0.7 mmol) and the mixture was stirred at 80C for 1 h. H20 and CH2CI2 were added and the phases were separated. The organic layer was dried (MgS04), filtered and concentrated. The crude product was purified by flash chromatography (heptane/EtOAc, 95:5? 0:100). tR: 1.10 min (LC-MS 2).

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, 717843-56-6, 3-Bromo-2-methoxy-5-methylpyridine.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98121-41-6, 3-Amino-5,6-dichloropyridine, 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, 98121-41-6, blongs to pyridine-derivatives compound. name: 3-Amino-5,6-dichloropyridine

EXAMPLE 11 5,6-dichloro-3-pyridinol Process (a) 8.15 g (50 mmol) of 3-amino-5,6-dichloropyridine were dissolved in 100 ml of 8N H2 SO4 and diazotized at 0 C. using 3.55 g (53 mmol) of sodium nitrite in 9 ml of water. The cold diazonium salt solution was added dropwise to 100 C. warm 60% strength sulfuric acid. After completion of the nitrogen elimination, the mixture was neutralized and extractively distilled using toluene. The dried toluene phase was concentrated by evaporation and the residue was recrystallized repeatedly from toluene. Melting point 184-185 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98121-41-6, its application will become more common.

Reference:
Patent; Hoechst Aktiengesellschaft; US4756739; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-78-9, 2-Chloro-5-(trichloromethyl)pyridine, 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, 69045-78-9, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Example 1 In a 120 cc autoclave equipped with a magnetic stirrer, 2-chloro-5-trichloromethylpyridine (11.5 g), Raney nickel (1.15 g) and a 70% aqueous solution of ethylamine (32.2 g) were charged. Hydrogen gas was introduced into the autoclave to a pressure of 10 Kg/cm2, and an internal temperature was raised to 45 C. At the same temperature, the hydrogen gas was supplied under a hydrogen pressure of 5 to 12.5 Kg/cm2. The absorption of hydrogen ceased after 70 minutes from the start of hydrogen supply. After completion of reaction, the autoclave was cooled to room temperature, and the catalyst was filtrated off from the reaction mixture. The filtrate was adjusted to pH 12.9 with a 48% aqueous solution of sodium hydroxide and the filtrate was concentrated. Water was added to the concentrate, and the product was extracted with toluene twice. After phase separation, the toluene layer was concentrated to obtain a concentrate (8.0 g) containing 2-chloro-5-ethylaminomethylpyridine, which was analyzed by gas chromatography to find that a yield of 2-chloro-5-ethylaminomethylpyridine was 77%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-78-9, its application will become more common.

Reference:
Patent; Koei Chemical Co., Ltd.; US5424437; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem