Day: April 18, 2022

Adding a certain compound to certain chemical reactions, such as: 22282-96-8, 2-Bromo-6-methyl-5-nitropyridine, 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, 22282-96-8, blongs to pyridine-derivatives compound. Product Details of 22282-96-8

To a stirred solution of 6-bromo-2-methyl-3-nitropyridine (15 g, 69.12 mmol) in ethanol (280 mL) was added iron powder (57.9 g, 1036 mmol) followed by conc HCl (30 mL). The reaction mixture was stirred for 6 h at 100 C., after completion of reaction (monitored by TLC), reaction mixture was cooled to room temperature, filtered through celite. Filterate was basified with saturated NaHCO3 solution, extracted with EtOAc. Organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was used in next step without further purification to afford desired compound (5.6 g, 65%) as an off-white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-96-8, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (141 pag.)US2016/347717; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 107867-51-6, 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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine. A new synthetic method of this compound is introduced below.

B. 6-Trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one Add 1,1′-carbonyldiimidazole (1.0 g, 6.17 mmol)to a solution of 5-trifluoromethyl-pyridine-2,3 diamine (0.90 g, 5.08 mmol) in CH2Cl2 (10 mL) and stir at room temperature for 18 hours. Heat the solution to reflux for 2 hours and filter the precipitate to obtain 6-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107867-51-6, 5-(Trifluoromethyl)pyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; US2003/36652; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10177-08-9, 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 10177-08-9, name is 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-Oxo-5-phenyl-l,2-dihydro-pyridine-3-carboxylic acid (44 g, 0.20 mmol) in tetrahydrofuran (5 mL) were successively added aniline (20 muL, 0.23 mmol), hydroxybenzotriazole (30 mg, 0.23 mmol), dimethylaminopyridine (27 mg, 0.23 mmol) and EDC (43 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with DCM containing 10percent of MeOH to afford the title compound as a white solid (20 mg, 34percent yield). MS (ES+) 291. deltaH (DMSOd6) 7.2 (3H, m), 7.9 (IH, t), 8.5 (IH, d), 8.6 (2H, m), 9.3 (IH, s).

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 10177-08-9, 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/65946; (2006); 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.1142197-14-5, name is 2-Bromo-5-cyclopropylpyridine, molecular formula is C8H8BrN, molecular weight is 198.06, as common compound, the synthetic route is as follows.category: pyridine-derivatives

n-Butyllithium solution (1.6 M in hexane, 0.61 mL, 0.98 mmol) was added to a flask with diethyl ether (2.2 mL) at -78 C, followed by the dropwise addition of 2-bromo-5-cyclopropylpyridine (213 mg, 1.07 mmol), and the resulting mixture was stirred at -78C for 45 min. To the prepared aryllithium solution was added a solution of (7h) (100 mg, 0.244 mmol) in THF (1.1 mL) dropwise and the mixture was stirred at -78 C for 10 min. The reaction was quenched by the addition of water. The dry ice bath was removed and then saturated aq. NLLCl solution was added. The resulting mixture was warmed to rt and the solution was extracted (EtOAc). The combined organic layer was washed (brine), dried (Na2SC>4), and concentrated under reduced pressure. Purification of the residue by column chromatography (30% to 60% (0610) acetone/hexanes, a gradient elution) provided the title compound (7i) (99 mg, 77%) as a yellow solid m/z (ESI, +ve ion) 529.2 = [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1142197-14-5, 2-Bromo-5-cyclopropylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; REW, Yosup; SUN, Daqing; YE, Qiuping; ZHOU, Haiying; KAWAI, Hiroyuki; MOORE, Jared; PHAM, Johnny; WU, Kejia; ZHU, Liusheng; (116 pag.)WO2020/76999; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66909-38-4, Adding some certain compound to certain chemical reactions, such as: 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine,molecular formula is C6H7ClN2, 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 66909-38-4.

A mixture of 6-chloro-4-methyl-pyridin-3-ylamine (1.53 g, 11 mmol), sodium methanesulfinate (1.60 g, 16 mmol), copper catalyst (0.50 g, 0.99 mmol), and N1,N2-dimethylethane-1,2-diamine (0.214 mL, 2.0 mmol) in 20 mL DMSO was heated under microwave irradiation at 150 C. After 2 h, mixture was poured into ca. 200 mL water and extracted five times with ca. 200 mL AcOEt. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (AcOEt/hexane 5:1?AcOEt) to give 6-methanesulfonyl-4-methyl-pyridin-3-ylamine as a white solid (0.534 g, 27%). 1HNMR (DMSO-d6, 400 MHz) delta 2.4 (s, 3H), 3.08 (s, 3H), 6.08 (s, 2H), 7.59 (s, 1H), 7.97 (s, 1H). Exact mass calculated for C7H10N2O2S 186.05, found 187.0 (MH+).

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. 66909-38-4, 6-Chloro-4-methylpyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jones, Robert M.; Lehmann, Juerg; Wong, Amy Siu-Ting; Hurst, David; Shin, Young-Jun; US2006/155128; (2006); 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.1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.COA of Formula: C6H4ClF3N2

To a solution of S.6 (205 mg, 0.64 mmol) in methylene chloride (4 mL) at RT was added oxalyl chloride (160 muL, 0.0019 mol) followed by the addition of DMF (50 muL) and stirred at RT for 1 hr. Separately a solution of A.6 (132 mg, 0.000672 mol), acetonitrile (2 ml) and pyridine (520 muL, 0.0065 mol) was stirred at RT followed by the addition of chlorotrimethylsilane (100 muL, 0.0008 mol). The acid chloride was concentrated under reduced pressure to a tan solid and redissolved in acetonitrile (2 mL). To the acid chloride solution was added the activated aniline. After 3 hr, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with dilute citric acid (50 mL), aqueous sodium bicarbonate (50 mL) and water. The organic layer was dried over sodium sulfate and concentrated to a residue which was purified by to give compound S.7. LCMS m/z: 498.95 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 103058-87-3, 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 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 1; 4- (5-formgammal-6-methoxypyridin-3-gammal) benzonitrile; A mixture of 5-bromo-2-methoxynicotinaldehyde (2.0 g) synthesized by a known method (Journal of Heterocyclic Chemistry 1985, 22(6), 1583-1592), (4- cyanophenyl) boronic acid (1.36 g) , Pd(PPh3)4 (0.32 g) and potassium carbonate (2.6 g) in THF (20 mL) and water (10 mL) was heated under reflux for 12 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated under reduced pressure. The obtained residue was crystallized from acetone/ethanol/IPE to give the title compound (0.93 g) as white crystals . melting point: 157C

According to the analysis of related databases, 103058-87-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/89031; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92138-35-7, 6-Chloro-3-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, Product Details of 92138-35-7, blongs to pyridine-derivatives compound. Product Details of 92138-35-7

100 L jacketed reactor equipped with a temperature probe, nitrogen inlet and reflux condenser was charged with toluene (27.0 L, 30 vol.) and EtOH (5.4 L, 6 vol.) followed by 6-chloro-3-nitropyridin-2(1H)-one (900.0 g, 5.15 mol) and phenyl boronic acid (640.4 g, 5.253 mol). The mixture was stirred at ambient temperature for 15 minutes before a solution of K2CO3 (173.9 g, 11.33 mol) in DI water (5.4 L, 6 vol.) was added. The reaction mixture was degassed with argon for 30 minutes at room temperature. Tetrakis triphenylphosphine palladium (178.2 g, 3 mol %) was added and the solution was heated to 95-100 C. (internal temperature was 77-79 C.) and stirred for 3 hours. After 3 hours HPLC showed 2.8% of starting material and another single impurity (15.3%, 1.17 RRT). The reaction was maintained for 3 hours at same temperature. After 6 hours, there was no progress in the reaction and the mixture was cooled to room temperature, degassed for 30 minutes, and another 5.0 g of tetrakis triphenylphosphine palladium was added and the solution was heated to 95-100 C. Reaction was deemed complete after one hour by HPLC. The reaction mixture was cooled to room temperature, the reaction was diluted with DI water (11.7 L, 13 vol.) followed by EtOAc (18.0 L, 20 vol.) and stirred for 1 hour. The two layers were separated, leaving the solids in aqueous layer. The aqueous layer was extracted with EtOAc (13.5 L, 15 vol.). The combined aqueous layers were neutralized pH to 6.2-6.8 with 3N HCl, when more solids precipitated out, the solids were filtered off, washed with water (2×2.5 L, 5 vol.) and dried under vacuum at 45-50 C. for 48 hours, to furnish 1a (761.1 g, 68.9% yield, 78.0% purity) as yellow solid. The compound was characterized by 1H NMR (DMSO-d6) and MS. (0157) The combined organic (ethyl acetate) layers were extracted with 3N NaOH (15 L), when solids were formed. The organic layer was separated. The aqueous layer was then acidified pH to 5-6 with 3N HCl, when more solids were precipitated out, which were filtered off and washed with DI water (2.0 L) and dried to obtain compound 1a (140.0 g, 12.7%, 93.8% purity, 2nd crop).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; Bates, Craig; Chen, Jian-Xie; Mao, Jianmin; Reed, David P.; US2015/266876; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-06-6, Methyl 5-bromo-4-methylpicolinate, 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, Product Details of 886365-06-6, blongs to pyridine-derivatives compound. Product Details of 886365-06-6

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (300 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), bis(pinacolato)diboron (364 mg, 1.43 mmol), and potassium acetate (384 mg, 3.91 mmol). Under nitrogen, anhydrous 1,4-dioxane (6.5 mL) was added and the vial was sealed. The reaction mixture was stirred at 120 C. for 18 h. After cooling to rt, under nitrogen, to the reaction vessel was added (+-)-(trans)-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (447 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), and potassium carbonate (540 mg, 3.91 mmol), and water (1.3 mL). The vial was sealed and stirred at 100 C. for 23 h. The reaction mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-85:15) to afford the target compound as a brown solid (126 mg, 21% over 2 steps); 1H NMR (400 MHz, DMSO-d6) delta 10.95 (s, 1H), 9.38 (s, 1H), 8.71 (s, 1H), 8.28 (s, 1H), 8.01 (s, 1H), 7.56 (s, 1H), 7.37 (br s, 2H), 7.29 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H), 3.77 (s, 3H), 2.25-2.16 (m, 2H), 1.90 (s, 3H), 1.43-1.34 (m, 1H), 1.24-1.14 (m, 1H).

The synthetic route of 886365-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1620-71-9, 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.1620-71-9, name is 5-Methyl-2-(trifluoromethyl)pyridine, molecular formula is C7H6F3N, molecular weight is 161.12, as common compound, the synthetic route is as follows.

Step A: 5-methyl-2-(trifluoromethyl)pyridine 1-oxide 5-methyl-2-trifluoromethyl-pyridine (commercially available, 0.164g) was dissolved in dichloromethane (5 mL). Meta-chloroperoxybenzoic acid (m-CPBA, 0.486 g) was added, and the mixture was stirred 48 hours at ambient (rt) temperature. The solvent was remove under reduce pressure and the crude product was purified by chromatography (solvent: isohexane/diethyl ether 7/3 to diethylether) to give the title compound (120mg) as a white solid. 1H NMR (300MHz, CDCI3): oe (ppm) 8.17 (s, 1H), 7.57 (d,1H), 7.16 (d, 1H), 2.38 (s, 3H) ppm.

Statistics shows that 1620-71-9 is playing an increasingly important role. we look forward to future research findings about 5-Methyl-2-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HALL, Roger Graham; GOEGH, Tibor; JUNG, Pierre Joseph Marcel; EDMUNDS, Andrew; JEANGUENAT, Andre; MUEHLEBACH, Michel; STOLLER, Andre; (98 pag.)WO2016/20286; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem