Month: April 2022

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.887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, molecular formula is C6H3F3INO, molecular weight is 288.9938, as common compound, the synthetic route is as follows.HPLC of Formula: C6H3F3INO

Step 2:; The phenol 5a2 (125 g, 424 mmol) is placed in a 3-neck 2 L flask. Phenylphosphonic dichloride (500 mL) is added and the mixture heated to 136C under Ar with stirring. After consumption of starting material (about 4-5 h), the reaction is cooled to RT and carefully quenched by the slow addition of the reaction mixture to crushed ice (caution: very exothermic.). A white solid forms which is filtered. The solid is dissolved in EtOAc (2 L) and aqueous NaOH is added with stirring. A NaOH solution is added until the aqueous layer is neutral. The EtOAc layer is separated, washed with water and brine and dried over anhydrous Na2SO4. Removal of solvent gives a white solid which is washed with cold hexane to afford chloride5a3

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/76747; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156094-63-2 , The common heterocyclic compound, 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine, molecular formula is C7H8BrNO, 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.

General procedure: To a flame-dried flask containing z-BuOK (1.10 equiv.) and anhydrous DMF (2.5 mL/mmol) was added ethyl 2-((diphenylmethylene)amino)acetate (1.05 eq. ) at 0 C under argon. After 10 min, arylmethyl bromide (1.0 eq.) was added. The resulting reaction mixture was stirred at 0 C for 10 min and was allowed to warm up to 4 C and stirred at 4 C overnight. The reaction mixture was then slowly poured into water, extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure to evaporate the DCM solvent. The residue was then treated with a mixture of EtOH/concentrated HC1 (25:1 v/v). The resulting solution was stirred at room temperature for 2 h. Upon the evaporation of EtOH and most of the DMF, the residue was basified by 2 N K2CO3 solution to pH > 10 and extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure. The residue was purified through flash chromatography on silica gel (1: 19 CH3OH/CH2CI2) to afford the desired ethyl 2-amino-3- arylpropanoate product as a colorless gel.

The synthetic route of 156094-63-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DE BRABANDER, Jef; ROSENBAUM, Daniel; LIANG, Qiren; WANG, Wentian; (343 pag.)WO2019/191327; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1070892-04-4, 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. 1070892-04-4, name is 5-Bromo-2-(trifluoromethyl)isonicotinonitrile, molecular formula is C7H2BrF3N2, 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 4-chloro-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl-5- (4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzenesulfonamide (150 mg, 0.34 mmol), 5-bromo-2-trifluoromethyl-isonicotinonitrile (111 mg, 0.44 mmol), Pd(Ph3P)4 (40 mg, 0.034 mmol) and Na2CO3 (217 mg, 2.1 mmol) in dioxane (2 ml.) and water (0.2 mL) was degassed with N2 for 5 min. The reaction vessel was sealed and then heated at 90 0C for 16 hrs. The mixture was absorbed onto silica gel and purified by chromatography on silica gel eluting with 20-25% acetone in hexanes to give 4-chloro- 5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(4-hydroxy-butoxy)-N-methyl-N-pyridin-2-yl- benzenesulfonamide as an oil (69 mg). A small sample was also purified by prep. LCMS. MS: 541.1 (M+H)+; tR = 7.59 min (method 2).

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 1070892-04-4, 5-Bromo-2-(trifluoromethyl)isonicotinonitrile.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (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. 144584-32-7, name is 3-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, 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. Recommanded Product: 3-Bromo-2,4-dichloropyridine

A. Preparation of 1-(3-bromo-4-chloropyridin-2-yl)hydrazine To stirring anhydrous dioxane (30 mL) at room temperature was added anhydrous hydrazine (3.29 mL, 105 mmol), followed by portion-wise addition of solid 3-bromo-2,4-dichloropyridine (2.39 g, 10.53 mmol, prepared as described in M. A. Walters, et al., Synth. Comm., Vol. 22, pp. 2829-2837, 1992). The resulting turbid solution was stirred in a 65 C. oil bath for 2 h. After cooling to room temperature, the reaction mixture was evaporated to dryness under reduced pressure. The resulting residue was triturated with isopropanol (50 mL), in which it was only partially soluble, and the mixture was filtered, collecting the solid. The filtrate was evaporated, and the resulting solid was triturated once again with isopropanol (25 mL) and filtered, collecting the solid. The two crops of solid were combined and dried in a 50 C. vacuum oven to obtain 1.438 g of an off-white solid, which contained about 70% of the title compound 1-(3-bromo-4-chloropyridin-2-yl)hydrazine and about 30% of its regioisomer (1-(3-bromo-2-chloropyridin-4-yl)hydrazine). HPLC/MS: retention time=1.06 min, [M+H]+=221.

With the rapid development of chemical substances, we look forward to future research findings about 144584-32-7.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 124236-37-9 ,Some common heterocyclic compound, 124236-37-9, molecular formula is C8H6F3NO2, 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 mixture of 5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (2.7 g, 13 mmol) and m-CPBA (CAN 937-14-4, 6.7 g, 39 mmol) in dry methylene chloride (30 mL) was stirred under reflux conditions overnight. Removal of the solvent in vacuo and purification of the obtained residue by column chromatography (silica gel, 15 g, 20% ethyl acetate in petroleum ether) provided the title compound (2.2 g, 76%) as light-yellow solid; MS (EI): m/e = 222.1 [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,124236-37-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 695-98-7, 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 695-98-7 as follows.

In dichloromethane (15.0 ml), 2,3,5-trimethyl-pyridine (1.29 g) was dissolved. The reaction solution was cooled to 0°C and added with meta-chloroperbenzoic acid (2.53 g), followed by stirring at room temperature for 1.5 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. Subsequently, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resulting residue in dichloromethane (25.0 ml). The reaction solution was added with trifluoroacetic anhydride (2.8 ml) and subjected to thermal reflux for 3.5 hours. After the reaction solution had been cooled to room temperature, the solvent was distilled off. The residue obtained was dissolved in methanol (60.0 ml). After having been cooled to 0°C, the reaction solution was added with a 12.5percent sodium methoxide/methanol solution to adjust to pH 10, followed by stirring at room temperature for 16.5 hours. After the solvent had been distilled off, the residue was added with distilled water and extracted with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resulting residue in chloroform (30.0 ml). The reaction solution was added with manganese dioxide (chemically processed product) (6.10 g) and then stirred at room temperature for 18 hours. The reaction solution was filtrated through Celite. The solvent in the filtrate was distilled off and the residue obtained was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.14 g) as a yellow oily substance. MS(FAB,Pos.):m/z=136[M+H]+1H-NMR(500MHz,CDCl3):delta=2.40(3H,s),2.63(3H,s),7.43(1H,brs),8.48(1 H,brs),10.16(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,695-98-7, its application will become more common.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, 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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

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 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) andPd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.? NMR (500 MHz, DMSO-<¾), delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS (M+l)+ = 169. At the same time, in my other blogs, there are other synthetic methods of this type of compound,880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine, and friends who are interested can also refer to it. Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; PASTERNAK, Alexander; DEJESUS, Reynalda, K.; TANG, Haifeng; PIO, Barbara; SHAHRIPOUR, Aurash; BELYK, Kevin, M.; CHOBANIAN, Harry, R.; GUO, Yan; FRIE, Jessica, L.; SHI, Zhi-Cai; CHEN, Helen; BLIZZARD, Timothy, A.; CATO, Brian; WO2013/66714; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52605-96-6, 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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.

To a solution of Compound 4 (100 mg) in 2-propanol (5 ml) were added 2-chloro-3-methoxy pyridine (182 mg) and concentrated sulfuric acid (165 mg). It was stirred under refluxing for 48 hours. The solvent was removed under reduced pressure. Saturated sodium bicarbonate solution and water were added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. The obtained residue was purified by column chromatography. The obtained solid was recrystallized with diethylether-hexane to give Compound I-17 (76.8 mg).1H-NMR (CDCl3) delta: 1.70 (3H, s), 3.88 (3H, s), 4.65 (2H, br), 6.23-6.33 (2H, m), 6.66 (1H, dd, J=10.2, 5.2 Hz), 6.91-7.02 (3H, m), 7.43 (1H, dd, J=7.1, 2.9 Hz), 7.78 (1H, dd, J=5.0, 1.3 Hz), 7.84-7.91 (1H, m)

Statistics shows that 52605-96-6 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-3-methoxypyridine.

Reference:
Patent; SHIONOGI & CO., LTD.; US2012/238557; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 74936-72-4, 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.74936-72-4, name is 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid, molecular formula is C16H16N2O6, molecular weight is 332.31, as common compound, the synthetic route is as follows.

(1) Preparation of (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (700 g, 2.1 mol) in methanol (14 L) was added Quinidine (617 g, 1.90 mol). The mixture was stirred at 90 C. under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for half an hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6%.

Statistics shows that 74936-72-4 is playing an increasingly important role. we look forward to future research findings about 5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Zhang, Hui; Fan, Mingwei; Sun, Liang; US2014/45896; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54232-43-8, 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 54232-43-8, name is 6-Bromo-5-methoxypicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 6-bromo-5-methoxy-pyridine-2-carboxylic acid (0.3 g, 1 mmol), 3-chlorophenylboronic acid (CAN 63503-60-6, 0.23 g, 1 mmol), tris(dibenzylidene-acetone)-dipalladium(0) (CAN 52409-22-0, 0.12 g), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (CAN 161265-03-8, 0.15 g) and potassium carbonate (0.21 g, 2 mmol) in 1,4-dioxane (10 mL) was stirred for 12 h at 110 C. under a nitrogen atmosphere. The reaction mixture was filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 10 g, eluting with 10% methanol in methylene chloride) to give the title compound (0.1 g, 29%); MS (EI): m/e=264.0 [M+H]+.

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 54232-43-8, 6-Bromo-5-methoxypicolinic acid.

Reference:
Patent; Bissantz, Caterina; Grether, Uwe; Hebeisen, Paul; Kimbara, Atsushi; Liu, Qingping; Nettekoven, Matthias; Prunotto, Marco; Roever, Stephan; Rogers-Evans, Mark; Schulz-Gasch, Tanja; Ullmer, Christoph; Wang, Zhiwei; Yang, Wulun; US2012/316147; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem