Day: March 18, 2022

Related Products of 1018505-59-3, 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. 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, 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 impure 5-(4-ethylpiperazin- 1 -yl)pyridin-2-amine (1.00 g, 4.85′ mmol assumed), 8-bromo-6-chloroimidazo[l ,2-a]pyridine hydrochloride salt (1.30 g, 4.85 mmol), 2,2′-bis(diphenylphosphino)-l,r-binaphthalene (634 mg, 1.02 mmol) and cesium carbonate (4.90 g, 15.0 mmol) in toluene (50 mL) was sparged with nitrogen while stirring for 10 min. Palladium(II) acetate (120 mg, 0.491 mmol) was then added and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted in a mixture of 1 : 1 methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1 : 19 methanol/methylene chloride to 1 :6methanol/methylene chloride) to afford 6-chloro-Ar-(5-(4-ethylpiperazin-l-yl)pyiidin-2- yl)imidazo[l,2-a]pyridin-8-amine as a yellow-green solid: NMR (400 MHz, DMS0- )d 9.12 (s, 1H), 8.30 (d, J = 2.0 Hz, 1H), 8.26 (d, J = 2.0 Hz, 1H), 7.99 (d, J = 2.8 Hz, 1 H), 7.89 (d, J = 0.8 Hz, 1H), 7.55 (d, J= 0.8 Hz, 1H), 7.43 (dd, J = 8.8, 2.8 Hz, 1H), 7.35 (d, J= 8.8 Hz, 1H), 3.11-3.10 (m, 4H), 2.50-2.49 (m, 4H, merged with DMSO peak), 2.38-2.37 (m, 2H), 1.04 (t, J= 7.2 Hz, 3H).

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter; CURRIE, Kevin, S; KROPF, Jeffrey, E.; LEE, Seung, H.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; XU, Jianjun; ZHAO, Zhongdong; WO2011/112995; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19235-89-3 ,Some common heterocyclic compound, 19235-89-3, molecular formula is C6H3ClN2, 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 teflon capped vial was charged with 4-amino-3- fluorophenol (0.291 g, 2.29 mmol) and anhydrous DMF (2.3 mL). The resultant solution was de-gassed in vacuo and backfilled with argon (3x). The vial was treated with sodium te/ -butoxide (0.27 g, 2.41 mmol) under argon and quickly capped. The reaction mixture was stirred at RT for lh. After addition of 4-chloropicolinonitrile (0.317 g, 2.29 mmol) and K2CO3 (0.174 g, 1.26 mmol), the vial was de-gassed again and heated in a 90 C oil bath overnight. The reaction mixture was diluted with EtOAc (60 mL) and washed with brine (25 mL). The aqueous phase was back-extracted with EtOAc (50 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO^, concentrated in vacuo and purified by chromatography to afford 4-(4-amino-3- fluorophenoxy)picolinonitrile (0.162 g, 31% yield) as a colorless oil. FontWeight=”Bold” FontSize=”10″ H NMR (DMSO- d6) delta 8.56 (d, J = 5.6 Hz, 1H), 7.62 (d, J = 2.0 Hz, 1H), 7.14 (dd, J = 6.0 , 2.8 Hz, 1H), 7.03 (dd, J = 1 1.6, 2.4 Hz, 1H), 6.88-6.77 (m, 2H), 5.25 (s, 2H); MS (ESI) m z: 230.0 (M+H+).

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. 19235-89-3, 4-Chloropyridine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel L.; PETILLO, Peter A.; KAUFMAN, Michael D.; WO2013/36232; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77555-27-2, 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. 77555-27-2, name is 2-(Pyridin-2-ylthio)ethanol. A new synthetic method of this compound is introduced below.

A solution of 0.2 g (0.55 mmol) of the product from example 11, Step C and 0.1 g (0.66 mmol) of the product from Example 23, step A in toluene (20 ml) was refluxed for 16 hours. The reaction mixture was partitioned between water and ethyl acetate. The combined organic layers were successively washed with water (25 ml x 2) and brine (25 ml x 2), dried over anhydrous sodium sulphate and evaporated under vacuo. The solid residue was purified by column chromatography over silica gel using 60 % ethyl acetate in hexane as the eluent to afford 0.1 g of the title compound as a yellow solid. ¹H NMR (400 MHz, DMSOd6) 8 3 – 3.11 (2H, t), 3.28 (2H, t), 3.55 – 3.56 (4H, t), 3.72 – 3.75 (4H, t), 6.92 – 6.95 (1H, d), 7.11 – 7.14 (1H, d), 7.35 – 7.37 (1H, d), 7.51 – 7.59 (3H, m), 7.62 – 7.67 (2H, m), 7.99 – 8.03 (3H, m), 8.08 – 8.14 (1H, m), 8.43 – 8.45 (1H, d), 9.08 – 9.13 (1H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77555-27-2, its application will become more common.

Reference:
Patent; TORRENT PHARMACEUTICALS LTD; WO2005/97746; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below.

To a solution of ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 5.51 mmol) in dimethylformamide was added slowly sodium hydride (242 mg, 6.06 mmol) at 0 C, followed by iodomethane (821 mg, 5.79 mmol). The mixture was stirred at same degree for 1 hour, and then quenched with water. The resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over MgS04 and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)propanoate (790 mg, 67 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,197376-47-9, Ethyl 6-Chloropyridine-3-acetate, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13817; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75358-90-6, 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 75358-90-6 as follows.

To a nitrogen flushed solution of Description 34 (14.27 g, 81 mmol) and conc. HC1 (15 ml) was added 10% Palladium on carbon (2 g), and the resulting mixture hydrogenated at 50 psi until HPLC and MS indicated complete conversion (approx 2 days). The catalyst was removed by filtration and the filtrate evaporated to give the title compound (17.55 g, 100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75358-90-6, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Limited; WO2004/46133; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90145-48-5, 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 90145-48-5, name is 5-Bromopyridine-2-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-1-isopropyl-3-methyl-1H-pyrazol-4-yf)-3-methyl-8-(4,4 5,5-tetramethyl- (1 ,3,2]dioxaborolan-2-yl)-1,3-d.hydroimidazo[4,5-c]quinolin-2-one (Stage 112.1.1 , 34 mg, 0.075 mmol), delta-bromo-py?dine^-carboxylic acid amide (Combi-Blocks, San Diego, USA, 20 mg, 0 099 mmol), and PdCI2(PPh3)2 (3.5 mg, O 005 mmol) in DMF (O 9 ml) and 1 M aqueous K2CO3 (0.187 ml) was stirred under argon at 105 C for 2.5 h The RM was cooled to rt. The mixture was diluted with MeOH + 3 drops TFA and purified directly by Prep.HPLC (H2O (0.1% TFA)/CH3CN 97:3 to 55:45). The fractions containing product were collected together and basifted with NaHCO3 (0.3 g), before being concentrated The resulting layer was extracted with DCM, washed with brine, dned over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (HPLC: tR 2.44 mm (Method A): M+H ~ 442 MS-ES; 1H-NMR (dbeta-DMSO, 400 MHz) 9.00 (s, 1H). 8 75-8 69 (m, 1H), 8.24-8.19 (m, 1H), 8.18-8.07 (m, 2H) 8.07-7.98 (m, 3H), 7.75-7.67 (m, 1 H), 7 61-7.56 (m, 1H)1 4.61-4 48 (m, 1H). 3.58 (s, 3H), 1 97 (s, 3H), 1.45 (s, 3H), 1.43 (s, 3H)).

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 90145-48-5, 5-Bromopyridine-2-carboxamide.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-78-9 ,Some common heterocyclic compound, 69045-78-9, molecular formula is C6H3Cl4N, 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.

REFERENCE EXAMPLE 1 A reaction was conducted for 12 hours in the same manner as in Example 1 except that 2-chloro-5-trichloromethylpyridine (0.2 mole) was replaced by 3-trichloromethylpyridine (0.2 mole). The resulting reaction mixture was analyzed by gas chromatography, which indicated that the amount of 3-cyanopyridine formed was 1% or less.

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; Ihara Chemical Industry Co., Ltd.; US5675012; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59942-87-9, 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.59942-87-9, name is Pyrazolo[1,5-a]pyridin-2(1H)-one, molecular formula is C7H6N2O, molecular weight is 134.1353, as common compound, the synthetic route is as follows.

52a. Synthesis of 4,5,6,7-tetrahydropyrazolo[1 ,5-a]pyridin-2-ol A solution of pyrazolo[1 ,5-a]pyridin-2-ol (7.5 g, 0.056 mol) in 280 mL of AcOH was hydrogenated over 2.5 g of 10 wt % Pd/C dry powder for 20 h under atmospheric pressure of hydrogen. After 72 h, the suspension was filtered over decalite and concentrated under vacuum to afford an orange residue that was suspended in hot IPA and stirred for 15 min, then cooled to 0 5C and filtered to afford 4.84 g of a cream colored solid. The filtrate was concentrated under vacuum, and recrystallyzed from EtOAc to afford additional 2.62 g (global 96%). 1 H NMR (CDCI3) delta ppm: 5.32 (s, 1 H), 3.91 (t, J = 6.1 Hz, 2H), 2.69 (t, J = 6.3 Hz, 2H), 2.06 – 1 .91 (m, 2H), 1 .86 – 1 .69 (m, 2H).

Statistics shows that 59942-87-9 is playing an increasingly important role. we look forward to future research findings about Pyrazolo[1,5-a]pyridin-2(1H)-one.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE S.A.; DIAZ FERNANDEZ, Jose Luis; CUBERES ALTISENT, Mª Rosa; WO2013/124341; (2013); 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-2-chloro-4-methoxypyridine

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

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, 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alexander; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda, K.; SUZUKI, Takao; WO2015/100147; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference 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 CaCl2 (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 at ambient 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 NaCl (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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,639091-75-1, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; GOETSCH, Liliane; JOUHANNEAUD, Alexandra; PEREZ, Michel; (129 pag.)WO2016/173682; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem