Month: February 2022

Synthetic Route of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. A new synthetic method of this compound is introduced below.

To a solution of tert10 butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (5 g, 14.61 mmol) in DCM (60 mL) andMeOH (18 mL), was added HC1 (4.0 M in dioxanes, 18 mL, 72 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was diluted with DCM and washed with 2N NaOH. The aqueous layer was extracted with DCM 2x and the combined organic layers were dried over Na2SO4, filtered and concentrated under reduce pressure to afford 514a (3.2 g,90.4%). MS (ESI) m/z 242.1 ([M+Hj . 1HNMR (400 MI-Tz, Chloroform-d) oe 8.18 (dd, J = 2.6,0.7 Hz, 1H), 7.52 (dd, J = 9.0, 2.6 Hz, 1H), 6.53 (dd, J = 9.1, 0.7 Hz, 1H), 3.54 – 3.40 (m, 4H),3.09 -2.87 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153747-97-8, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth M.; CHIN, Elbert; COTTELL, Jeromy J.; KATANA, Ashley Anne; KATO, Darryl; LINK, John O.; SHAPIRO, Nathan; TREJO MARTIN, Teresa Alejandra; YANG, Zheng-Yu; (395 pag.)WO2018/145021; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1262860-54-7, 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 1262860-54-7, name is 5-(2-Methoxyethoxy)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Compound 3 (180 mg, crude), ferf-butyl-(2-amino-4-(thiophen-2- yl)phenyl)carbamate (147 mg, 0.51 mmol) and EDCI (194 mg, 1.01 mmol) were combined in pyridine (4 mL). The reaction was stirred at rt overnight and (0241) concentrated in vacuo. The crude material was purified via column chromatography on silica gel (200-300 mesh, eluting with petroleum ether/EtOAc = 1 :1 ) to afford Compound 4 (175 mg, 40.8%).

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 1262860-54-7, 5-(2-Methoxyethoxy)picolinic acid.

Reference:
Patent; REGENACY PHARMACEUTICALS, LLC; VAN DUZER, John H.; MAZITSCHEK, Ralph; BLUM, Charles; JARPE, Matthew B.; (53 pag.)WO2020/76951; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1192813-41-4, 2-(Difluoromethoxy)-5-nitropyridine, 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-(Difluoromethoxy)-5-nitropyridine, blongs to pyridine-derivatives compound. Safety of 2-(Difluoromethoxy)-5-nitropyridine

To 2-(difluoromethoxy)-5-nitropyridine (4.7 g, 24.7mmol) in degassed methanol (100 mL) was added 10% palladium on carbon (500 mg, 0.47 mmol) and the reaction was hydrogenated at atmospheric pressure for 1 hour. To this was added acetic acid (2.83 ml., 49.4 mmol) and the reaction wasfiltered through Celite and concentrated in vacuo to afford6-(difluoromethoxy)pyridin-3-amine (6.33 g, 25.9 mmol,105% yield) as an olive green liquid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1192813-41-4, 2-(Difluoromethoxy)-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1211518-35-2, 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. 1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate, molecular formula is C8H5ClF3NO2, 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.

Sodium hydride (1.1 g, 31.4 mmol) was added in portions to cyclopropylmethanol (20 mL) and the mixture was stirred at room temperature for 0.5 hours. 6-Chloro-5- (trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (1.5 g, 6.3 mmol) was added and the resulting solution was stirred at 80C for 1 h. Water (20 mL) was added; the solution was acidified with 6 N hydrochloric acid and then concentrated to give a residue which was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous solution was extracted with ethyl acetate (2 x 20 mL) and the combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude target compound. The crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether) to give the title compound (1.4 g, 85%) as white solid; MS (EI): m/e = 262.0 [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 1211518-35-2, Methyl 6-chloro-5-(trifluoromethyl)picolinate.

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

Application of 1256785-40-6 ,Some common heterocyclic compound, 1256785-40-6, molecular formula is C7H7ClN2O2, 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.

To a stirred suspension of LiAlH4 (1.0 g, 26.3 mmol) in dry THF (500 mL) at 0 C. under nitrogen was added dropwise a solution of 4-amino-6-chloro-nicotinic acid methyl ester (2.6 g, 13.9 mmol) (from Example 22 supra) in THF (100 mL). After the addition, the reaction mixture was stirred at this temperature for 1 hour. The reaction was quenched slowly with water (1.5 mL) and filtered. The organic solution was evaporated to give (4-amino-6-chloro-pyridin-3-yl)-methanol as a white solid which was used directly in the next step. (Yield 2.2 g, 100%). LC-MS: [M+H]+ 159.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256785-40-6, its application will become more common.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 811801-40-8, 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.811801-40-8, name is (3-((Pyridin-4-ylthio)methyl)phenyl)methanol, molecular formula is C13H13NOS, molecular weight is 231.31, as common compound, the synthetic route is as follows.

EXAMPLE 8 6,7-dichloro-2-cyclopentyl-2-methyl-5-({3-[(pyridin-4-ylthio)methyl]benzyl}oxy)indan-l-oneDitertbutylazodicarboxylate (129 mg, 0.56 mmol) was added to a stirred solution of 6,7- Dichloro^-cyclopentyl-S-hydroxy^-methylindan-l-one (500 mg, 1 mmol), {3-[(pyridin-4- ylthio)methyl]phenyl}methanol (65 mg, 0.28 mmol) and triphenylphosphine (147 mg, 0.56 mmol) in tetrahydrofuran (5 mL) at rt. The reaction mixture was stirred for 16 hr, then the solvent was removed in vacuo. The residue was purified via column chromatography on silica gel (eluting 0-80% ethyl acetate/hexanes) to give 6,7-dichloro-2-cyclopentyl-2-methyl-5-({3-[(pyridin-4- ylthio)methyl]benzyl}oxy)indan-l-one as a colorless oil. 1H NMR(CDCl3, 500MHz), ? 8.39 (d, 2H), 7.56-7.40 (m, 4H), 7.13 (d, 2H), 6.91 (s, IH), 5.23 (s, 2H), 4.26 (s, 2H), 2.97 (d, IH), 2.67 (d, IH), 2.26- 2.22 (m, IH), 1.88-1.83 (m, IH), 1.56-1.48 (m, 5H), 1.28-1.20 (m, 4H), 0.94-0.92 (m, IH). MS (ESI): 513 (M + H)+.

The chemical industry reduces the impact on the environment during synthesis 811801-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2006/47237; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83766-88-5, 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 83766-88-5, name is 2-(tert-Butoxy)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

According to the analysis of related databases, 83766-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98197-72-9, 4-Iodo-2-methoxypyridine, 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: C6H6INO, blongs to pyridine-derivatives compound. Formula: C6H6INO

(d) 50.6 mL of isopropyl magnesium chloride (2 mol/L tetrahydrofuran solution) was cooled with ice, and a solution having 19.8 g (84.3 mmol) of the crude product of 4-iodo-2-methoxypyridine obtained in step (c) dissolved in 80 mL of tetrahydrofuran, was added, followed by stirring at 0C for 1 hour and at room temperature for 1 hour. Then, 16.9 g (127 mmol) of N-chlorosuccinimide was gradually added, followed by stirring at room temperature for 1 hour. 100 mL of water was added to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. Extraction with ethyl ether was carried out, then the organic layer was dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 11.0 g (crude yield 91%) of a crude product of 4-chloro-2-methoxypyridine.1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 3.91(s, 3H), 6.70(d, 1H, J = 2.0 Hz), 6.81(dd, 1H, J = 6.0 Hz, 2.0 Hz), 7.99(d,1H, J = 6.0 Hz)

The synthetic route of 98197-72-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1559320; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of 3-chloro-pyridine-4-carboxylic acid methyl ester (0.28 g, 1.65 mmol) in DMF (10 ml) are added cesium carbonate (2.68 g, 8.25 mmol) and 3,3-difluoro-3-(4-fluorophenyl)-propane-1 -thiol (synthesized according to the methods described in sections a) and b) of example 3) (0.34 g, 1.65 mmol) in a sealed tube. The reaction mixture is stirred at 90C for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3 x 20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% acetone/hexane) to yield 3-[[3,3- difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.19 g, 0.56 mmol, 34%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; GRUNENTHAL GMBH; LUCAS, Simon; KUeHNERT, Sven; BAHRENBERG, Gregor; SCHROeDER, Wolfgang; WO2014/82737; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 902837-42-7, 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. 902837-42-7, name is 7-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below.

Sodium hydride (0.25 g, 6.2 mmol) is added under ice bath cooling to a mixture of 7-bromo-lH-pyrrolo[3,2-c]pyridine (0.8 g, 4.1 mmol) in DMF (10 ml). The mixture is stirred for 30 minutes before methyl iodide (0.25 ml, 4.1 mmol) is added. The mixture is warmed to RT and stirred for 17 h. The mixture is diluted with DCM and extracted with a saturated aqueous sodium hydrogencarbonate solution. The combined organic layers are dried over MgS04 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 0.61 g (71%). HPLC-MS: tR=0.88 min (METHOD l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,902837-42-7, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; WO2015/25018; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem