Day: March 12, 2021

Electric Literature of 16498-81-0, 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.16498-81-0, name is 2-Methoxynicotinic acid, molecular formula is C7H7NO3, molecular weight is 153.14, as common compound, the synthetic route is as follows.

To a 100-mL round-bottomed flask was added 2-methoxynicotinic acid (1.52 g, 9.93 mmol, Aldrich, St. Louis, MO) and borane methyl sulfide complex (3.77 mL, 39.7 mmol, Aldrich, St. Louis, MO) in tetrahydrofuran (30 mL). The reaction mixture was stirred at 70 C for 16 h. The mixture was cooled to 0 C and MeOH (10 mL) was added dropwise. After the addition was completed, the reaction mixture was stirred for further 20 min. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 60% EtOAc/hexanes to give (2-methoxy-3-pyridinyl)methanol (1.15 g) as a white solid.

Statistics shows that 16498-81-0 is playing an increasingly important role. we look forward to future research findings about 2-Methoxynicotinic acid.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael David; BO, Yunxin; BRYAN, Marian C.; CROGHAN, Michael; FOTSCH, Christopher Harold; HALE, Clarence Henderson; KUNZ, Roxanne Kay; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis Dale; POON, Steve Fong; STEC, Markian Myroslaw; ST. JEAN, David, Joseph, Jr.; TAMAYO, Nuria A.; TEGLEY, Christopher Michael; YANG, Kevin Chao; WO2012/27261; (2012); A1;,
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 14482-51-0, name is 2-Bromo-3,5-dichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 14482-51-0

To a solution of 56 g (0.246 mol) of 2-bromo-3,5-dichloropyridine in 500 mL of dry dimethylsulfoxide, were added 53 g (0.261 mol) of ethyl bromodifluoroacetate followed by 94 g (0.518 mol) of copper bronze (200 mesh). The suspension was stirred at 50 C for 5 hours. After cooling, a solution of 44 g (0.328 mol) of potassium monophosphate in 280 mL of water was added and stirred for 1 hour. The black mixture was filtered over a cake of Supercel, and the cake washed three times with 200 mL of ethyl acetate. The organic phases were collected, washed with brine and dried over magnesium sulfate. After evaporation of the solvent under vacuum 57.6 g of a brown oil were obtained. After purification by column chromatography over silica gel (heptane/ethyl acetate 9/1) 40 g (57%) of ethyl (3,5-dichloropyridin-2-yl)(difluoro)acetate (Int-5) were obtained as a yellow oil, (M+1) = 270, 19F-NMR (235MHz, CDCl3) delta (ppm): – 104.21 (CF2).

With the rapid development of chemical substances, we look forward to future research findings about 14482-51-0.

Reference:
Patent; Bayer CropScience AG; The designation of the inventor has not yet been filed; EP2606727; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 586-98-1, 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 586-98-1, name is Pyridin-2-ylmethanol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: GeneralProcedure for the preparation of 2-Phenyl-1H-benzoimidazole (3aa): A 25mL over-dried Schlenk tube was charged with 2-nitroaniline (41.4 mg, 0.3 mmol),benzyl alcohol (97.2 mg, 0.90 mmol) and Pd(dppf)Cl2 (12.2 mg, 0.015mmol). The tube was purged with nitrogen three times. Toluene (1 mL) was addedto the sealed reaction vessel by syringe. The reaction mixture was stirred in apreheated oil bath at 160 oC for 24 h. After cooling to roomtemperature, the reaction mixture was then concentrated in vacuo, and theresidue was purified by column chromatography (silica gel, petroleumether/ ethyl acetate = 4:1) to give 3aa as a pale yellow solid (56.5 mg, 97%).

According to the analysis of related databases, 586-98-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Xiaotong; Hu, Renhe; Tong, Yao; Pan, Qiang; Miao, Dazhuang; Han, Shiqing; Tetrahedron Letters; vol. 57; 41; (2016); p. 4645 – 4649;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 62733-99-7, 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. 62733-99-7, name is Methyl 3-hydroxypicolinate. A new synthetic method of this compound is introduced below.

To a solution of 3-hydroxy-pyridine-2-carboxylic acid methyl ester (200 mg, 1.3 mmol) in N,N-dimethylformamide (2.0 ml) was added at 22 C sodium hydride (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0 C and treated with trifluoro ethyl trifluormethanesulfonate (728 mg) and stirring was continued at 22 C for 2 hours. The mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate, and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane and ethyl acetate (3: 1) as the eluent to give 3-(2,2,2- trifluoro-ethoxy)-pyridine-2-carboxylic acid methyl ester as a pale green oil. MS (ESI): m/z = 236.2 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62733-99-7, Methyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BANNER, David; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander V.; ROGERS-EVANS, Mark; WO2011/70029; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 102368-13-8, 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 102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one). This compound has unique chemical properties. The synthetic route is as follows.

Example 74 1-(2-Azidoethoxy)-4-isothiocyanatomethyl-2-methoxy Benzene (34) A solution of 33 (0.115 g, 0.33 mmol) in DMF (1.5 mL) was treated with NEt3 (0.037 g, 0.36 mmol) and stirred for 1 h. The mixture was treated with 1,1-thiocarbonyl di-2(1H)-pyridone (0.084 g, 0.33 mmol) and stirred for 2.5 h at room temperature. The mixture was diluted with H2O and extracted with diethyl ether several times. The combined organic layer was washed with H2O and bnine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel using EtOAc:Hex (1:2) as eluant to give 34 as oil (0.065 g, 74%) 1H NMR (CDCl3) delta 6.75-6.91 (m, 3H, Ar), 4.65 (s, 2H, CH2N=C=S), 4.20 (t, 2H, OCH2), 3.90 (s, 3H, OCH3), 3.62 (t, 211, CH2N3)

According to the analysis of related databases, 102368-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pacific Corporation; Digital Biotech Co., Ltd.; US6476076; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7379-35-3, 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. 7379-35-3, name is 4-Chloropyridine hydrochloride. A new synthetic method of this compound is introduced below.

To a solution of 4-aminothiophenol (20.2 g, 156.5 mmol) in anhydrous DMF (200 mL) was added 4-chloropyridine hydrochloride (24.4 g, 161.0 mmol) followed by potassium carbonate (44 g, 318.4 mmol). The reaction mixture was heated at 80¡ã C. overnight, then diluted with ethyl acetate (400 mL) and water (400 mL). The aqueous layer was back-extracted with ethyl acetate (2.x.200 mL). The combined organic layers were washed with a saturated aqueous NaCl solution (200 mL), dried over anhy MgSO4, and concentrated under reduced pressure. The residue was filtered through a pad of silica with ethyl acetate and the resulting material was triturated with an ethyl ether/hexane solution to afford the desired product (24.7 g, 78percent). TLC (50percent ethyl acetate/50percent hexane) Rf 0.25; 1H-NMR (DMSO-d6) delta 5.67 (bs, 2H), 6.65 (d, J=8.4 Hz, 2H), 6.88 (d, J=6.2 Hz, 2H), 7.19 (d, J=8.4 Hz, 2H), 8.27 (d, J=6.2 Hz, 2H), MS[M+H]+=203.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7379-35-3, 4-Chloropyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CORPORATION; US2004/2507; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14254-57-0 ,Some common heterocyclic compound, 14254-57-0, molecular formula is C6H4ClNO, 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 solution of (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate hydrochloride (150. mg, 0.380 mmol) in DCM (10.0 mL) at 0 C. was treated with EtN (0.170 mL, 1.22 mmol) and stirred for 20 min. Isonicotinoyl chloride (88.0 mg, 0.490 mmol) was then added and the mixture was stirred for 2 h. The reaction was treated with saturated aqueous solution of ammonium chloride (50 mL) and extracted with DCM (2¡Á50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to afford the title compound (100. mg, 60%). LC/MS: Rt=1.49 min, ES+ 461 (FA standard).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14254-57-0, its application will become more common.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/51404; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58530-53-3, Adding some certain compound to certain chemical reactions, such as: 58530-53-3, name is 2,4-Dibromopyridine,molecular formula is C5H3Br2N, 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 58530-53-3.

In a 1L round-bottom flask are combined 2,4-dibromopyridine (20.0 g, 84.6 mmol), copper iodide (3.22 g, 16.9 mmol), 1,10-phenanthroline (6.10 g, 33.8 mmol), cesium carbonate (110 g, 338 mmol), Celite (16 g) and p-xylene (170 mL). To the resulting slurry is added 2-bromo-4-methylaniline (10.6 mL, 84.6 mmol) and nitrogen is bubbled through the vigorously stirred mixture for 10 minutes. The flask is fitted with a reflux condenser and the system is heated at 135C for 24 hours. The reaction mixture is cooled to room temperature and filtered. The filter cake is rinsed with methylene chloride and ethyl acetate and the combined organic filtrates are concentrated under reduced pressure over silica gel. The crude reaction product is purified by chromatography on silica gel using a gradient of 0 to 10% ethyl acetate in methylene chloride. The resulting brown solid is slurried in methylene chloride and triturated using hexanes, then isolated by filtration to provide the title compound (6.52 g, 25.0 mmol, 30% yield) as a shiny yellow solid: 1H NMR (400.13 MHz, DMSO-d6 with TFA-d) ppm: 9.40 (dd, J=0.9, 7.2 Hz, 1H), 8.45 (dd, J=0.7, 1.8 Hz, 1H), 8.42 (bs, 1H), 7.86 (dd, J=2.1, 7.3 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.64 (dd, J=0.9, 8.4 Hz, 1H), 2.57 (s, 3H); 13C NMR (100.62 MHz, DMSO-d6 with TFA-d) ppm 142.6, 134.6, 131.9, 130.8, 129.9, 129.4, 127.0, 119.7, 115.0, 113.8, 113.4, 21.1; HRMS (m/z): found: 261.0013 (M+H), calcd for C12H10N2Br: 261.0027, Err=-5.4 ppm.

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. 58530-53-3, 2,4-Dibromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; ATTARDO, Giorgio; HORCHLER, Carey; XIONG, Hui; (53 pag.)WO2017/83198; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 106877-33-2, 5-Amino-2-(trifluoromethyl)pyridine, 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, Formula: C6H5F3N2, blongs to pyridine-derivatives compound. Formula: C6H5F3N2

Thionyl chloride (31 mL, 0.43 mol) was slowly added to 175 mL, of water at 0 C. During the addition the temperature was maintained between 0-5 C. After addition the solution was warmed to 15 C. and 0.47 g (4.8 mmol) of CuCl was added. The solution was diluted with 100 mL of water and cooled back to 0 C. A solution of 7.21 g (0.10 mol) of NaNO2 in 100 mL, of water was slowly added to a solution of 15.39 g (0.10 mol) of 5-amino-2-(trifluoromethyl)pyridine (95) in 125 mL of conc. HCl at 0 C. During addition the temperature was maintained between 0-5 C. This mixture was then slowly added to the above prepared solution so as to maintain a temperature between 0-5 C. A voluminous precipitate formed. The mixture was stirred for an additional 30 min after addition and the solid was then collected by filtration. The solid was washed with water and dissolved in CHCl3. The solution was dried over MgSO4, filtered and the solvent was removed to afford 18.03 g (77%) of sulfonyl chloride (83) as a tan solid. 1H NMR (CDCl3) delta 9.34 (d, J=2.2 Hz, 1 H), 8.53 (dd, J=8.4, 2.2 Hz, 1H), 7.98 (d, J=8.4 Hz, 1H).

The synthetic route of 106877-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Konradi, Andrei W.; Probst, Gary; Aubele, Danielle L.; Garofalo, Albert W.; Hom, Roy; Neitzel, Martin L.; Semko, Christopher M.; Truong, Anh P.; US2008/21056; (2008); A1;,
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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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. Computed Properties of C7H5BrN2

Step-i: 5-Bromo-3-iodo-1H-pyrrolo[2.3-b ]pyridinePCT/IB2013/0553885-Bromo-1H-pyrrolo[2,3-b]pyridine (5 g, 25 mmol) was dissolved in anhydrous acetone (7510 ml) and added N-iodo succinimide (6.18 g, 27.5 mmol) under nitrogen atmosphere and stirredat RT for 2 h. The reaction was monitored by TLC (10% Ethyl acetate in hexane). Thereaction mixture was cooled to RT and filtered, washed with cold acetone (50 ml) and driedunder vacuum to afford 7.05 g (87% yield) of 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine.MS: m/z = 324.6 (M+1); HPLC: 91.11% in method B.

With the rapid development of chemical substances, we look forward to future research findings about 183208-35-7.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UM PHARMAUJI SDN. BHD; GUMMADI, Venkateshwar, Rao; HOSAHALLI, Subramanya; NANDURI, Srinivas; AGGUNDA RENUKAPPA, Girish; WO2014/6554; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem