Month: April 2022

Application of 60186-15-4, 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. 60186-15-4, name is 2,4-Difluoro-5-nitropyridine, molecular formula is C5H2F2N2O2, 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.

To a solution of 2,4-difluoro-5-nitropyridine (335 mg, 2.093 mmol) in THF (10 mL) at – 40C, was added via cannula 2-methylmorpholine (80 mg, 0.791 mmol) dissolved in THF (1 mL) followed by Et3N (0.583 mL, 4.19 mmol). The cloudy yellow mixture was stirred at -40 C for 1 h and was allowed to warm to 0C. After stirring an additional 2 h, TLC (50% ethyl acetate in hexanes) showed a more polar spot with a small amount of starting material remaining. The mixture was concentrated. The product was purified by column chromatography on silica gel (20%? 50% ethyl acetate in hexanes; 25 g column) to afford 4-(2-fluoro-5-nitropyridin-4-yl)-2-methylmorpholine (264 mg, 1.094 mmol, 52% yield) as a yellow oil: NMR (400MHz, CDCh) delta 8.63 (s, 1H), 6.42 (s, 1H), 4.04 – 3.95 (m, 1H), 3.89 – 3.76 (m, 2H), 3.26 – 3.17 (m, 3H), 2.87 (dd, J=12.8, 10.0 Hz, 1H), 1.24 (d, J=6.3 Hz, 3H); 19 F NMR (376MHz, CDCh) delta -61.49 (s, IF); LC/MS (ESI) m/e 242.1 [(M+H)+, calcd for C10H13FN3O3 242.1].

According to the analysis of related databases, 60186-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (104 pag.)WO2018/98411; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 173528-92-2, 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. 173528-92-2, name is HMN-154. A new synthetic method of this compound is introduced below.

Example 1 (E)-4-[2-{2-[N-phenoxycarbonyl-N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl]pyridine 1.00 g of (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl ]pyridine was suspended in 40 ml of chloroform and, after adding 1.82 g of phenyl chlorocarbonate, 1.20 g of triethylamine was slowly added under ice cooling. Then, the mixture was stirred at room temperature for 5 minutes. The solvent was distilled off under reduced pressure and the desired product was purified by silica gel column (carrier:Wako Gel C200, developing solvent chloroform) to obtain the desired compound. The desired compound was treated with ethanol to obtain 0.71 g of a white granular crystal.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,173528-92-2, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1382335; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 886371-28-4, name is 3-Bromo-6-chloroimidazo[1,2-a]pyridine. A new synthetic method of this compound is introduced below., Formula: C7H4BrClN2

To a solution of 3-bromo-6-chloro-imidazo[1,2-a]pyridine (1 eq, 18.1 mmol, 4.2 g), 2- chloropyridin-4-yl boronic acid (1.05 eq, 19 mmol, 3 g), Na2COs (2 eq, 36.2 mmol, 3.84 g) in dioxane (30 ml) and water (10 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (1.23 g). The reaction mixture is heated at 100 C for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgStheta4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound; [M+H]+ =264 (266).

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, 886371-28-4, 3-Bromo-6-chloroimidazo[1,2-a]pyridine.

Reference:
Patent; NOVARTIS AG; WO2009/50183; (2009); A2;,
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. 1227605-52-8, name is 2-Bromo-5-chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H3BrClNO

To a solution of 2,3-dibromo-5-chloropyridine (60 g, 221 mmol) in THF (500 mL) was added a solution of isopropylmagnesium chloride lithium chloride solution in THF (1 .3M, 185 mL) at -40 C over about 30 mm. The solution was stirred for 30 mm at -40 C and DMF (50 mL) was added. The resulting solution was warmed up to room temperature and stirred for 30 min. The reaction was quenched with 1 N HCl (400 mL) and MTBE (200 mL) was added. Organic layer was separated and washed twice with 5% aqueous NaHCO3 (200 mL). The solvent was removed under vacuum at 50 C. The resulting solids (aldehyde intermediate) were dissolved in methanol (400 mL). The solution was cooled to 5 C under an ice bath. NaBH4 (3.6 g) was added slowly over 30 min while maintaining the reaction temperature below room temperature. The reaction mixture was stirred for another 30 min followed by addition of water (125 mL). The resulting mixture was concentrated under vacuum to approximately 150 ml. Solids precipitated during the concentration. The suspension was stirred vigorously at room temperature for 1 h and solids were collected by filtration. The wet cake was dried in a vacuum oven over night at 60 C to give 52 (45.6 g, 93%) as a solid. 1H NMR (CDCl3, 400 MHz): oe 8.26 (d,J=2.5 Hz, 1H), 7.88 (d,J2.5 Hz, 1H), 4.73 (d,J 5.8 Hz, 2H), 2.33 (t,J= 11.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz): oe 147.12, 138.48, 138.39, 136.14, 132.06, 62.76.

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, 1227605-52-8, 2-Bromo-5-chloronicotinaldehyde.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHEN, Frank; MOLINARO, Carmela; WUELFING, W. Peter; YASUDA, Nobuyoshi; YIN, Jianguo; ZHONG, Yong-Li; LYNCH, Joseph; ANDREANI, Teresa; WO2013/169348; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19346-44-2, 2-Fluoro-3-nitro-5-methylpyridine, 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, Safety of 2-Fluoro-3-nitro-5-methylpyridine, blongs to pyridine-derivatives compound. Safety of 2-Fluoro-3-nitro-5-methylpyridine

3-Amino-2-fluoro-5-methylpyridine was prepared analogously from 2-fluoro-5-methyl-3-nitropyridine. This compound was obtained in 89 percent yield as white solid melting at 27-28.5 C. Elemental Analysis C6 H7 FN2 Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 56.9, %H, 5.65; %N, 22.6 1 H NMR CDCl3: 7.2 (d, 1H); 6.8 (d, 1H); 3.7 (br, 2H); 2.1 (s, 3H); 13 C NMR CDCl3: 151.8 (d, J=229); 134.5 (d, J=12.6); 132.2 (d, J=3.9); 129.9 (d, J=28.7); 125.8 (d, J=5.3), 17.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19346-44-2, 2-Fluoro-3-nitro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; DowElanco; US5461161; (1995); A;,
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 40473-07-2, name is 2-Bromo-6-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H6BrNO

To a solution of the compound of Preparation 113 (5.6 g, 29.8 mmol) in anhydrous tetrahydrofuran (100 ml), at -78° C. and under nitrogen, was added n-butyllithium (1.6M in hexane, 19.5 ml), via syringe. The mixture was stirred at -78° C. for 30 min, before addition of N,N-dimethylformamide (2.5 ml, 32.8 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18 h, before being acidified with sulphuric acid (2M) and then neutralised by addition of sodium hydrogen carbonate. The mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (4*150 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (3.0 g). 1H-NMR (CDCl3): 4.01-4.05 (3H), 6.95-7.00 (1H), 7.54-7.58 (1H), 7.70-7.76 (1H), 9.95-9.98 (1H)

With the rapid development of chemical substances, we look forward to future research findings about 40473-07-2.

Reference:
Patent; PFIZER LIMITED; US2008/103130; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1003711-43-0 , The common heterocyclic compound, 1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine, molecular formula is C6H6BrNO, 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.

0.49 g (6.82 mmoi) cyclopropane methanol in 10 mL THF are charged with 0.42 g (11.4 mmoi) NaH and the reaction mixture is stirred at r.t. for 20 min. Then 1.00 g (5.68 mmoi) 5-bromo-2-fluoropyridine are added and the mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, dried over MgS04l filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (MeOH/H20/FA). CgH-ioBrNO (M= 228.1 g/mol) ESI-MS: 228/229 [M+H]+ Rt (HPLC):1.14 min (method C) The following compounds are prepared analogously to example XXV.1 ; For example XXV.4 the reaction conditions are 50 C for 4 h. For examples XXV.10 – XXV.13 and XXV.19 – XXV.21 the reaction time is 2 h. For example XXV.9 no solvent is used and the reaction temperature is 95 C. For the examples XXV.4, XXV.10 – XXV.12, XXV.15 – XXV.16 and XXV.19 – XXV.21 the reaction is done in DMF. For example XXV.18 the reaction is done in DMSO at 100 C. For example XXV.21 toluene is used as solvent and the reaction conditions are 50 C for 1 h. For example XXV.22 methyltetrahydrofurane is used as solvent at 0 C for the deprotonation and 50 C for the substitution..

The synthetic route of 1003711-43-0 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 1093879-46-9 ,Some common heterocyclic compound, 1093879-46-9, 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.

To a mixture of 2-(6-bromo-2-pyridyl)acetic acid (500 mg, 2.31 mmol) and ethyl 2- amino-2-methyl- propanoate (426 mg, 2.55 mmol, CAS 17288-15-2) in DMF (10 mL) was added HATU (1.14 g, 3.01 mmol) and DIPEA (897 mg, 6.94 mmol). Then the mixture was stirred at 20 C for 12 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was washed with water (50 mL) and extracted with ethyl acetate (3 X 50 mL). The organic layer was dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-column chromatography (petroleum ether:ethyl acetate = 1:1) to give the title compound (580 mg, 76% yield) as a yellowish oil. LCMS: (ES+) m/z (M+H)+= 328.9, tR = 0.742

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1093879-46-9, its application will become more common.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); 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.956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine, molecular formula is C7H4F3N3, molecular weight is 187.12, as common compound, the synthetic route is as follows.Quality Control of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

To compound 12 (150 mg, 0.80 mmol) and benzene-1,2-diamine (104 mg, 0.96 mmol) was added a 1N aqueous sodium hydroxide solution (3.0 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The mixture was diluted with water and extracted twice with ethyl acetate. The solvent was evaporated, and the residue was purified by preparative HPLC to yield 80 mg (42 %) of the title compound as a white solid. 1H NMR (400MHz, DMSO-d6): delta 7.19-7.29 (m, 2H), 7.39 (dd, J=8.1, 4.4Hz, 1H), 7.53 (d, J=7.1Hz, 1H), 7.74 (d, J=7.1Hz, 1H), 8.65 (dd, J=4.4, 1.0Hz, 1H), 8.85 (dd, J=7.8, 1.0Hz, 1H), 13.12 (br s, 1H), 14.19 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 111.5, 112.8, 118.2, 119.0, 121.6, 122.9, 131.3, 134.2, 135.6, 143.8, 146.5, 149.7, 152.7. HRMS m/z calcd for C13H9N5 + [H+]: 236.0931; found: 236.0936.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,956010-87-0, 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, 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. Product Details of 99368-68-0

The crude 6-chloro-5- (trifluoromethyl) pyridin-3-amine 5(crude 1.3 g, 6.61 mmol) was dissolved in pyridine (10 ml), then 4-dimethylaminopyridine (DMAP) (50 mg) was added. di -t- butyl dicarbonate(2.17g) was added dropwise, and the mixture was stirred for 4 hours at 22 . Toluene (20ml) was added, all solvent was removed under reducedpressure. The residue was filtered through a plug of silica gel (hexane/ ethyl acetate 2: 1), to obtain t- butyl N-6- chloro-5- (trifluoromethyl)pyridin-3-yl carbamate 6.

With the rapid development of chemical substances, we look forward to future research findings about 99368-68-0.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; JUNG, MICHAEL E; SAWYERS, CHARLES L; OUK, SAMEDY; TRAN, CHRIS; WONGVIPAT, JOHN; (40 pag.)JP2016/11315; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem