Month: April 2022

Electric Literature of 99368-68-0, 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 99368-68-0 as follows.

A solution of 6-chloro-5-(trifluoromethyl)pyridin-3-amine (0.35 g, 1.78 mmol) in acetic anhydride (6 mL) was heated at 100 C. for 12h. The solution was evaporated until dryness. The residue was taken up in DCM. The organic layer was washed with a 10% aqueous solution of K2CO3, separated, dried over MgSO4, filtered and evaporated to give a crude product (0.44 g, 100%). This compound was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99368-68-0, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; LU, Tianbao; CONNOLLY, Peter J.; CUMMINGS, Maxwell David; DIELS, Gaston Stanislas Marcella; THURING, Jan Willem; PHILIPPAR, Ulrike; EDWARDS, James Patrick; BERTHELOT, Didier Jean-Claude; WU, Tongfei; (65 pag.)US2019/381012; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 156094-63-2, Adding some certain compound to certain chemical reactions, such as: 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine,molecular formula is C7H8BrNO, 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 156094-63-2.

[00602] A 60 % dispersion of sodium hydride in mineral oil (0.019 g, 0.493 mmol) was added to a stirred solution of 2-(phenoxymethyl)-6,7-dihydropyrazolo[l,5-a]pyrazin- 4(5H)-one (0.1 g, 0.411 mmol) in DMF (4 mL) at 0 C. The mixture was stirred at room temperature for 15 min. Then 2-bromomethyl-6-methoxypyridine (0.99 g, 0.493 mmol) was added and the mixture was stirred at room temperature for 16 h. The mixture was cooled at 0 C, treated with water and extracted with AcOEt. The organic layer was separated, washed with brine, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash chromatography (silica; EtOAc in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to afford an impure product that was repurified by flash column chromatography (silica; DCM). The desired fractions were collected and the solvents evaporated in vacuo. The desired product was triturated with diethyl ether and filtered to yield 5-[(6-methoxypyridin-2-yl)methyl]-2-(phenoxymethyl)-6,7- dihydropyrazolo[l,5-a]pyrazin-4(5H)-one (0.105 g, 70.5% yield). C2oH2oN403 *H NMR (400 MHz, CDC13) delta ppm 3.87 (s, 3 H) 3.90 – 3.98 (m, 2 H) 4.37 – 4.44 (m, 2 H) 4.76 (s, 2 H) 5.09 (s, 2 H) 6.65 (d, J=8.1 Hz, 1 H) 6.90 (d, J=7.2 Hz, 1 H) 6.93 – 7.04 (m, 4 H) 7.26 – 7.33 (m, 2 H) 7.54 (dd, J=8.2, 7.3 Hz, 1 H).

According to the analysis of related databases, 156094-63-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P., Jeffrey; LINDSLEY, Craig, W.; STAUFFER, Shaun, R.; BARTOLOME-NEBREDA, Jose Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; TONG, Han Min; ALCAZAR-VACA, Manuel Jesus; ANDRES-GIL, Jose Ignacio; WO2013/192350; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 670253-37-9 ,Some common heterocyclic compound, 670253-37-9, molecular formula is C5H4ClIN2, 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 suspension of 4-chloro-5-iodopyridin-2- amine (2.54 g, 10.0 mmol), sodium thiomethoxide (1.40 g, 20.0 mmol), copper(l) iodide (190 mg, 1.00 mmol), potassium carbonate (2.76 g, 20.0 mmol) and ethylene glycol (1.12 ml_, (1026) 20.0 mmol) in I PA (3 ml_) was stirred at 80 C under an N2 atmosphere for 19 h. The reaction mixture was allowed to cool to rt, filtered through Celite and the solids were washed using MeOH (3 x 20 ml_). The combined filtrates were concentrated under reduce pressure and water (30 ml_) was added to the residue. The resulting suspension was extracted with DCM (3 x 20 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash (1027) chromatography (20%; then 30%; then 40% EtOAc in cyclohexane (isocratic)) to give the title compound (779 mg, 44%) as an off-white crystalline solid. LCMS (Method A): RT = (1028) 0.41 min, m/z = 175, 177 [M+H]+. 1 H NMR (500 MHz, DMSO-cfe): d 8.01 (s, 1 H), 6.59 (s, 1 H), 6.34 (s, 2H), 2.32 (s, 3H).

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. 670253-37-9, 4-Chloro-5-iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ROUNTREE, James Samuel Shane; WHITEHEAD, Steven Kristopher; TREDER, Adam Piotr; PROCTOR, Lauren Emma; SHEPHERD, Steven David; BURKAMP, Frank; COSTA, Joana Rita Castro; O’DOWD, Colin; HARRISON, Timonthy; (333 pag.)WO2019/150119; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1227594-89-9, 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 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Step 8(f): 3-fluoro-1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridin-2(1 H)-one (8-8) To a solution of 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (8-5; 50 mg; 0.34 mmol) in dioxane 1.7 mL) was added K2CO3 (51 mg; 0.373 mmol) and the mixture was stirred for 5minutes. 5-(chloromethyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (8-4; 68 mg; 0.373 mmol) was then added, and the mixture was stirred for 2 hours at room temperature. The mixture was diluted with water, and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by ISCO CombiFlash provided the title compound. 1H NMR (400 MHz, CDCl3): delta 10.14 (s, 1 H); 8.11 (d, J=5.2 Hz, 1 H); 7.18 (t, J=4.7 Hz, 1 H); 5.40 (s, 2 H); 3.41 (s, 3 H).

According to the analysis of related databases, 1227594-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Burch, Jason; Cote, Bernard; Nguyen, Natalie; Li, Chun Sing; St-Onge, Miguel; Gauvreau, Danny; US2011/245296; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866775-18-0, Adding some certain compound to certain chemical reactions, such as: 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate,molecular formula is C8H6BrF3N2O2, 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 866775-18-0.

A suspension of 3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) (1.00 g, 3.34 mmol) in dry MeOH (20 ml) was stirred at reflux (85 C) for 30 min and then treated with hydrazine monohydrate (324 ul, 6.69 mmol). The mixture was returned to heat at reflux for 5h 30 min and allowed to cool to RT. Water was added and the resulting precipitate was collected by filtration and dried in a vacuum oven to afford the title compound as a biege solid; 1 H NMR (400 MHz, DMSO-d6) ? 9.50 (1 H, s), 7.69 (1 H, s), 7.19 (2H, s), 4.55 (2H). LCMS: Rt =1.15 min; [M+H]+ 299 Method 2minl_C_v002.

According to the analysis of related databases, 866775-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUTLER, Rebecca; COLLINGWOOD, Stephen, Paul; HALL, Edward, Charles; EDWARDS, Lee; LEGRAND, Darren, Mark; SPIEGEL, Katrin; WO2013/38386; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 709652-82-4, 2-Amino-5-bromonicotinonitrile, 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-Amino-5-bromonicotinonitrile, blongs to pyridine-derivatives compound. Safety of 2-Amino-5-bromonicotinonitrile

Example 126 Step 1: (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)nicotinonitrile To a stirred solution of 2-amino-5-bromonicotinonitrile (100 mg, 0.51 mmol) and 1,2- dimethoxyethane (4 mL) in a microwave vial equipped with a stirbar was added bis(pinacolato diborane) (175 mg, 0.66 mmol), potassium acetate (149 mg, 1.52 mmol) and 1,1′- bis(diphenylphosphino)ferrocene-palladium(II)dichloride (21 mg, 0.025 mmol). The mixture was purged with nitrogen gas for 5 min and the reaction mixture was stirred at 90 C for 3 h. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo affording a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile used for the next step without any further purification.

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
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. 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

Compound 12 (500 mg, 2.67 mmol) was suspended in aqueous ammonia solution (33 %, 10 mL). The mixture was heated in a sealed tube in the microwave oven to 140 C for 10 min. Volatiles were evaporated. To the residue was added ethyl acetate (100 mL) and tert-butyl methyl ether (25mL), and the mixture was heated to 70 C. The hot mixture was filtered, and the residue was washed with tert-butyl methyl ether. The combined filtrates were evaporated to yield the title compound as slightly yellow residue (389 mg, 90 %), which contained traces of corresponding primary amide. 1H NMR (400MHz, DMSO-d6): delta 7.47 (dd, J=8.2, 4.5Hz, 1H), 8.46 (dd, J=8.2, 1.5Hz, 1H), 8.73 (dd, J=4.5, 1.5Hz, 1H), 15.02 (br s, 1H). 13C NMR (125MHz, DMSO-d6): delta 113.5, 115.5, 116.9, 119.6, 128.7, 150.9, 151.0. HRMS m/z calcd for C7H4N4: 144.0436; found: 144.0430.

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, 956010-87-0, 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
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. 41288-96-4, name is 2-Chloro-5-hydroxypyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 41288-96-4

4) 2-Chloro-5-methoxypyridine; To a solution of the 2-chloro-5-hydroxypyridine (1.30 g) and methyl iodide (1.25 ml) in N,N-dimethylformamide (26 ml) was added dropwise 28% solution of sodium methoxide in methanol (2.0 ml), and the mixture was stirred at room temperature for 1.5 hours. Saturated aqueous ammonium chloride and ethyl acetate were added to the reaction liquid, then the phases were separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by chromatography on silica gel (hexane-ethyl acetate) to give 2-chloro-5-methoxypyridine (1.40 g, 98%) as a solid. 1H-NMR (400 MHz, CDCl3)delta: 3.85 (3H, s), 7.17-7.25 (2H, m), 8.05 (1H, d, J = 2.9 Hz). LC-MSm/z: 144 (M+H)+.

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, 41288-96-4, 2-Chloro-5-hydroxypyridine.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1698626; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 185017-72-5, 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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, 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 3-bromo-2-chloro-6-methylpyridine (60 mg, 0.291 mmol) in DMA (2 mL) was added 2- (cyclopentyldifluoromethyl) oxazole (50 mg, 0.267 mmol) , KOAc (55 mg, 0.560 mmol) and Pd (PPh3)4(30 mg, 0.026 mmol) under N2atmosphere and the mixture was stirred at 80 overnight. Then the mixture was cooled to rt, filtered and the filtrate was concentrated in vacuum, the residue was purified by prep. TLC (EA: PE5: 1) to give the title compound. MS: 313 (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 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 176526-00-4 ,Some common heterocyclic compound, 176526-00-4, molecular formula is C12H9NO, 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.

(b) 4-[2-((E)-2-Iodovinyl)phenyl]pyridine: In a similar manner to that of Example 1(d), starting with 1.98 g (10.8 mmol) of 2-pyrid-4-ylbenzaldehyde obtained in Example 50(a), 490 mg (15%) of the expected compound are obtained in the form of a green oil. 1 H NMR (CDCl3) delta 6.84 (d, 1H, J=14.8 Hz), 7.28 to 7.51 (m, 7H), 8.69 (d, 2H, J=5.5 Hz).

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. 176526-00-4, 2-(Pyridin-4-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Centre International de Recherches Dermatologiques; US6150413; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem