Day: September 16, 2021

Related Products of 63897-12-1, 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 63897-12-1, name is 2,4-Dichloro-6-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-aminopyrazine (0.900 g, 9.47 mmol) in DMSO (40 mL) was added potassium tert-butoxide (2.13 g, 18.9 mmol) followed by 2,4-dichloro-6-methyl-3-nitropyridine (2.00 g, 9.47 mmol). After stirring for 30 min at rt, sat. NH4Cl solution was added. The organic layer was separated and the water layer was extracted with CH2Cl2 three times. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Chromatography on silica gel (0-70% ethyl acetatehexanes) provided the desired product (567 mg, 23%). MS (ESI) mass calcd. C10H8ClN5O2, 265.04. m/z found, 266.0 [M+H]+. 1H NMR (500 MHz, CDCl3) delta 8.69-8.62 (br s, 1H), 8.38-8.34 (m, 2H), 8.34-8.29 (m, 2H), 2.59-2.56 (m, 3H).

According to the analysis of related databases, 63897-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Alcazar Vaca, Manuel Jesus; Andres Gil, Jose Ignacio; Chrovian, Christa C.; Coate, Heather R.; De Angelis, Meri; Dvorak, Curt A.; Gelin, Christine F.; Letavic, Michael A.; Savall, Brad M.; Soyode-Johnson, Akinola; Stenne, Brice M.; Swanson, Devin M.; US2014/275015; (2014); 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. 1628-89-3, name is 2-Methoxypyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

A 5-liter three-necked round bottom flask was equipped with an overhead mechanical stirrer under nitrogen, the flask was charged with THF (1 L) and cooled to -78 C. To this stirred solution was added tert-butyllithium (1.7 M solution in pentane) (800 mL, 1.36 mol) via canula followed by 2-methoxypyridine (132.2 g, 1.21 mol) at -78 C. The mixture was stirred for 1 h at -78 C. To the mixture was added N-formyl-N, N’, N’-trimethylethylenediamine (176 mL, 1.37 mol) dropwise at -78 C. The reaction mixture was stirred for ca. 30 min at -78 C. before warming to -23 C. over ca. 30 min. To the mixture at -23 C. was added ethylene glycol dimethyl ether (1 L) followed by n-butyllithium (2.5 M solution in hexane) (800 mL, 2.0 mol). The resulting mixture was stirred for ca. 2 h during which time the reaction mixture turned deep green. A 12-L 4-necked round flask was charged with iodine (571 g, 2.25 mol) and ethylene glycol dimethyl ether (2 L) and the resultant solution was cooled to -78 C. The contents of the 5-L flask were transferred via canula to the mixture of iodine and ethylene glycol dimethyl ether in the 12-L flask at -78 C. After the addition was complete, the reaction mixture was stirred for an additional 1 h at -78 C. The cooling bath was removed and the mixture was allowed to warm to about 0 C. and treated with 2 L of water and 2 L of 1 N hydrochloric acid. Methyl t-butyl ether (2L) was added and the layers were separated. The aqueous layer was extracted with 2×1 L of methyl t-butyl ether. The combined organic layers were washed with saturated Na2S2O3 (1.2 L), brine (1.2 L), dried over Na2SO4. After concentration in vacuo, the thick slurry was diluted with hexane (1 L). The mixture was cooled with an ice/water bath for ca. 30 min. The precipitate was filtered and dried in vacuum to yield the title compound as a light yellow solid. 1H NMR (300 MHz, CDCl3) delta 10.22 (s, 1H), 7.86 (1H, d, J=5.3 Hz), 7.54 (1H, d, J=5.3 Hz), 4.06 (3H, s). LCMS (M+H)+ m/z 364 (t=2.26 min.).

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, 1628-89-3, 2-Methoxypyridine.

Reference:
Patent; Wittman, Mark D.; Balasubramanian, Neelakantan; Velaparthi, Upender; Zimmermann, Kurt; Saulnier, Mark G.; Liu, Peiying; Sang, Xiaopeng; Frennesson, David B.; Stoffan, Karen M.; Tarrant, James G.; Marinier, Anne; Roy, Stephan; US2004/44203; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 644-98-4 ,Some common heterocyclic compound, 644-98-4, molecular formula is C8H11N, 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.

Preparation: (i?)-2-methyl-N-((5′)-2-methyl- 1 -phenyl-2-(pyridine-2-yl)propyl)propane-2- sulfinamide.To a 1.0 Molar solution of potassium t-butoxide in tetrahydrofuran (3000 mL, 3.000 moles) was added diisopropylamine (425 mL, 306.8 g, 3.032 moles). The resulting solution was cooled by a dry ice / acetone bath to -5O0C. w-Butyllithium solution (980 mL of 2.5 Molar, 2.450 moles) was added drop wise over a period of 40 minutes, giving a bright orange solution. The mixture was allowed to stir for an additional 20 minutes at -250C, then was cooled back down to -550C. 2-isopropylpyridine (1) (240.0 g, 1.981 moles) was then added drop wise over a period of 20 minutes while maintaining the internal temperature between – 5O0C to -550C, giving a deep, reddish-purple solution. The mixture was allowed to stir for an additional 2 hours at -5O0C, then was used directly in the next step.To the cooled (-5O0C) mixture containing the 2-Isopropylpyridyl anion was added a solution of (R,E)-N-benzylidene-2-methylpropane-2-sulfinamide (2) (360.0 g, 1.720 moles) in anhydrous tetrahydrofuran (3000 mL), drop wise over a period of 3 hours while maintaining the internal temperature between -5O0C and -550C. The reaction mixture was allowed to warm gradually over 3 hours to O0C, then checked for completion by working up an aliquot and checking by HPLC. The reaction was quenched by treatment with saturated sodium bicarbonate solution (3000 mL), added drop wise over 20 minutes. After stirring for an additional 30 minutes, the mixture was further diluted with water (3000 mL), and divided into three portions (~4500mL each). Each portion was partitioned with ethyl acetate (1000 mL), and the layers separated. The combined aqueous layer was further extracted with ethyl acetate (3 x 1000 mL). The combined organic extracts were washed with saturated brine (1500 mL), then dried (anhydrous magnesium sulfate). Filtration, followed by removal of the solvent under reduced pressure, left the crude product as a cream-colored solid (575.8g, 101.3% crude yield), which was a 9: 1 mixture of diastereomers. The crude material was recrystallized from a mixture of Hexane / EtOAc (2: 1) to give pure desired single diastereomer (371.9g, 65.4% yield). IH NMR (300 MHz, CHLOROFORM-d) delta ppm 8.62 (dd, J=4.85, 1.05 Hz, 1 H) 7.52 (td, J=7.80, 2.11 Hz, IH) 7.09 – 7.19 (m, 4 H) 6.99 (d, J=8.01 Hz, 1 H) 6.85 – 6.94 (m, 2 H) 5.80 (d, J=8.01 Hz, 1 H) 4.49 (d, J=8.43 Hz, 1 H) 1.46 (s, 3 H) 1.33 (s, 3 H) 1.10 (s, 9 H). MS: m/z 331.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,644-98-4, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; BALESTRA, Michael; BERNSTEIN, Peter; ERNST, Glen, E; FRIETZE, William; MCCAULEY, John P; NUGIEL, David; SHEN, Lihong; WO2010/74647; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1186647-69-7, 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.1186647-69-7, name is 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H3ClIN3, molecular weight is 279.47, as common compound, the synthetic route is as follows.

To a solution of 4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (2.00 g, 7.17 mmol) in DMF (30 mL) was added KOH (0.800 g, 14.3 mmol) and 1-(chloromethyl)-4-methoxybenzene (2.24 g, 14.3 mmol). The mixture was stirred at room temperature overnight. After concentration, the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (10:1 to 8:1) to give the title compound as a white solid (2.4 g, 82%).

The chemical industry reduces the impact on the environment during synthesis 1186647-69-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Estrada, Anthony; Shore, Daniel; Sweeney, Zachary; US2014/288043; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69872-17-9 ,Some common heterocyclic compound, 69872-17-9, molecular formula is C7H5BrN2, 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.

step 1 : A mixture of 4-bromo-lH-pyrrolo[2,3-c]pyridine (320 mg, 1.62 mmol), Pd(dppf)Cl2 (131 mg, 0.179 mmol), zinc cyanide (190 mg, 1.62 mmol), and zinc powder (21 mg, 0.324 mmol) in DMF (20 mL) was stirred at 120 C for 2 h. The reaction mixtue was cooled to RT andH20 (100 mL) was added. The reaction mixture extracted with EtOAc (3 x 50 mL). The organic layers were concentrated under reduced pressure and the crude residue was purified by S1O2 chromatography eluting with petroleum ether/EtOAc (1 :1) to afford 232 mg (99.8%) of lH-pyrrolo[2,3-c]pyridine-4-carbonitrile as yellow solid: MS (ESI) m/z: 144.2 [M+l] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69872-17-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James John; MATHIEU, Simon; RUDOLPH, Joachim; LEE, Wendy; WO2013/92940; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211580-54-9, 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. 1211580-54-9, name is 4-Bromo-2-(difluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

[0208] Step 2: (R)-benzyl 7-(3-(2-(difluoromethyl)pyridin-4-yl)-l-trityl- lH-indazol-5-yl)-6-oxo-2,7-diazaspiro[4.4]nonane-2-carboxylate : To a stirred solution of 4-bromo-2-(difluoromethyl)pyridine (0.520 g, 2.51 mmol) and bis(pinacolato)diboron (1.270 g, 5.02 mmol) in 1,4-dioxane (15 mL), was added potassium acetate (0.740 g, 7.53 mmol). The solution was degassed for 15 mins. [Iota, – bis(diphenylphosphino)ferrocene]dichloropalladium (II) DCM complex (0.102 g, 0.125 mmol) was added. The mixture was degassed for 10 mins followed by refluxing for 3 h. The mixture was cooled to rt and (i?)-benzyl 7-(3-iodo-l -trityl-lH-indazol-5-yl)-6-oxo- 2,7-diazaspiro[4.4]nonane-2-carboxylate (Intermediate 7) (1.523 g, 2.009 mmol) in ethanol: toluene: water (1 : 1 : 1, 15 mL) was added followed by potassium carbonate (1.733 g, 12.56 mmol). The solution was degassed for 20 mins. Tetrakis(triphenylphosphine)palladium(0) (0.145 g, 0.125 mmol) was added. The mixture was degassed for 10 mins followed by refluxing for 3 h. The mixture was cooled to rt and filtered through a Celite pad. To the filtrate was added cold water, and the mixture was extracted with ethyl acetate (3 X 50 mL). The combined organic layers were washed with water (30 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude compound was purified by column chromatography (100-200 silica) using 50% ethyl acetate in hexane as eluent to afford (i?)-benzyl 7-(3-(2- (difluoromethyl)pyridin-4-yl)-l -trityl-lH-indazol-5-yl)-6-oxo-2,7-diazaspiro[4.4]nonane- 2-carboxylate (0.500 g, 0.658 mmol, 33% yield ) as an off white solid . XH NMR (400 MHz, DMSO-de) delta 8.81 (d, J= 5.1Hz, 1H), 8.37 (d, J = 1.5 Hz, 1H), 8.09-8.00 (m, 2H), 7.50 (br d, J = 9.5 Hz, 1H), 7.43-7.27 (m, 14H), 7.20 (dd, J = 1.8, 7.7 Hz, 7H), 6.49 (d, J = 9.2 Hz, 1H), 5.08 (d, J = 3.3 Hz, 2H), 3.91 (br t, J = 6.4 Hz, 2H), 3.66-3.36 (m, 4H), 2.22-2.03 (m, 3H), 1.97 (br d, J = 4.8 Hz, 1H). LCMS : 260.44 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211580-54-9, 4-Bromo-2-(difluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter Qinhua; KAHRAMAN, Mehmet; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HOPKINS, Chad, Daniel; PINCHMAN, Joseph, Robert; ABRAHAM, Sunny; SIT, Rakesh, Kumar; SEVERANCE, Daniel, Lee; (248 pag.)WO2016/161160; (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. 89166-98-3, name is 3,4,5-Trichloropyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows. name: 3,4,5-Trichloropyridin-2-ol

Add 0.1 mol of 3,5,6,-trichloropyridinol, 150 ml of ethanol, 0.4 mol of ammonium formate, 0.2 g of Pd/C catalyst, stir and reflux to reflux at 65 C for 5 hours, and analyze the reaction process by thin layer chromatography. . Cool, filter, and filter cake with a small amount of ethanol. The mother liquor and the washing liquid were combined, concentrated, and the product was distilled under reduced pressure by an oil pump, and the yield was 87.3%. The filter cake is washed with water to remove inorganic salts, and the recovered palladium/carbon catalyst can be recycled.

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, 89166-98-3, 3,4,5-Trichloropyridin-2-ol.

Reference:
Patent; Zhejiang Sci-Tech University; Hong Xiaoping; Zhu Jintao; Meng Jing; (5 pag.)CN109836372; (2019); A;,
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. 82671-02-1, name is 2,6-Dichloro-5-fluoronicotinonitrile. A new synthetic method of this compound is introduced below., Computed Properties of C6HCl2FN2

Preparation 46; C- .-methylamine; Add to a Parr Bottle 2,6 dichloro-3-cyano-5-fluoropyridine (5g, 26.18mmol), ethanol (50ml), concentrated hydrochloric acid (4. 3ml) and 10% Pd-C (0. 5g). Place on a Parr Shaker Appartus under 36 psig hydrogen for 6 hours at ambient temperature. Add potassium acetate (10.28g, 104. 72mmol) and continue under 48 psig hydrogen overnight at ambient temperature. Filter the reaction over Celite and concentrate the filtrate under vacuum to a residue. Add to the residue THF (100ml). Filter the solid, and concentrate the filtrate under vacuum to give (5-Fluoro-pyridin-3-yl)-methylamine as a clear oil (6g). ‘H NMR (DMSO): 8.6 (d, 2H), 8.0 (d, 1H), 4.2 (s, 2H). MS (ES+) = 127.5

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, 82671-02-1, 2,6-Dichloro-5-fluoronicotinonitrile.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 98549-88-3, 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 98549-88-3 as follows.

To a mixture of methyl 2,4-difluoro benzoate (1.0 g) in 1,4-dioxane (20 mL), 5-hydroxypyrrolo[2,3-b]pyridine (779 mg) and K3P04 (1.47 g) were added at 34C and heated to90C. The reaction mixture is stirred at the same temperature for 23 hours. K3P04 (396mg) was added at 90C to the reaction mixture and stirred for another 24 hours at thesame temperature. Cooled the reaction mixture to 32C and filtered on a celite bed.Washed the celite bed with ethyl acetate (20 mL) and evaporated the solvent in the filtrateto obtain crude product. The crude product was purified by column chromatography using60-120 silica gel mesh and 10-50% ethyl acetate- hexane as eluent to obtain the titlecompound as white solid. Yield: 588 mg; Purity by HPLC: 98.73%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98549-88-3, its application will become more common.

Reference:
Patent; DR. REDDY?S LABORATORIES LIMITED; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; JURUPULA, Ramprasad; BAIG, Mohammed Azeezulla; CHAKKA, Ramesh; THIPPARABOINA, Rajesh; PEDDY, Vishweshwar; RAO, Pallavi; ORUGANTI, Srinivas; DAHANUKAR, Vilas Hareshwar; (88 pag.)WO2017/212431; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 34392-85-3 ,Some common heterocyclic compound, 34392-85-3, molecular formula is C6H7ClN2O, 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.

3-Amino-2-chloro-6-methoxypyridine (500 mg, 3.17 mmol) dissolved/suspended in conc. hydrochloric acid (10 mL) was stirred at -5 C. while a solution of sodium nitrite (1.09 g, 15.82 mmol) in water (5 mL) was added dropwise over 10 min. The mixture was stirred for a further 10 min before copper chloride (3.13 g, 31.65 mmol) was added portionwise over 5 min. The dark effervescing mixture was stirred at -5 C. for 20 min and then the cooling bath was removed and the mixture stirred at ambient temperature for 3 h. The mixture was diluted with water (100 mL), basified to pH 10-11 by addition of 5N sodium hydroxide (aq.) and extracted with diethyl ether (3 50 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:heptane (1:9, v/v) as eluent to afford the product as a pale yellow oil (229 mg, 41%).Data for 2,3-dichloro-6-methoxypyridine: MS (ESI) m/z: 178 ([M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34392-85-3, its application will become more common.

Reference:
Patent; N.V. Organon; US2007/112019; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem