Pyridine-derivatives

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 97483-77-7, name is 5-Bromopicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 97483-77-7

To a stirred solution of 5-bromopicolinonitrile (10 g) in dry THE (150 mL) was added methylmagnesium bromide (20 mL, 3 M in THE) at -20C. After addition, the mixturewas allowed to warm to RT with stirring for 30 minutes. The reaction mixture was then treated with MeOH (200 mL) and NaBH4 (4 g). The reaction was stirred at RT for 15 hours and then poured into a solution of NaOH in water (200 mL, 1 M). The organic solvent was removed under reduced pressure and the aqueous phase was extracted with EA (100 mL x 3). The combined organic phase was washed with brine (50 mL) and dried over Na2SO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with DCM/MeOH = 99:1 to provide the subtitle compound. MS ESI: mlz = 201 [M+H].

With the rapid development of chemical substances, we look forward to future research findings about 97483-77-7.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BUNING, Christian; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; HALLAND, Nis; LOHMANN, Matthias; POeVERLEIN, Christoph; RITTER, Kurt; WO2015/150564; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 162102-79-6, 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 162102-79-6 as follows.

To a solution of dimethyl 4-bromopyridine-2,6-dicarboxylate (CAS 162102-79-6) (2.40 g, 8.8 mmol, 1.0 eq) in MeOH/DCM solution (10/1, 88 mL) was added KOH (896 mg, 8.0 mmol, 0.9 eq) at rt. The reaction mixture was stirred at rt for 3 h and Et20 (80 mL) was added thereto. The resulting white solid was filtered and then redissolved in water (50 mL). 2 M HC1 solution (8 mL) was added. The mixture extracted with DCM (2 x 50 mL). The combined organic layers were washed with brine and dried over anhydrous Na2S04. After removing the solvent, the residue as brown solid was used directly in the next step without further purification (1.0 g, Y: 44%). ESI-MS (M+H) +: 259.9. 1H NMR (400 MHz, CDC13) delta: 8.56 (d, J = 1.7 Hz, 1H), 8.50 (d, J = 1.7 Hz, 1H), 4.04 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,162102-79-6, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; CHAN, Timothy; GUCKIAN, Kevin; JENKINS, Tracy; THOMAS, Jermaine; VESSELS, Jeffery; KUMARAVEL, Gnanasambandam; MEISSNER, Robert; LYSSIKATOS, Joseph; LUCAS, Brian; LEAF, Irina; DUFFIELD, Jeremy; (518 pag.)WO2016/11390; (2016); 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. 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride. A new synthetic method of this compound is introduced below., Formula: C7H8ClNO2

To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0 C was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0 C for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95%) was used in the next step without further purification.

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, 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; KEANEY, Gregg F.; WANG, John; GERARD, Baudouin; ARAI, Kenzo; LIU, Xiang; ZHENG, Guo, Zhu; KIRA, Kazunobu; TIVITMAHAISOON, Parcharee; PRAJAPATI, Sudeep; GEARHART, Nicholas C.; KOTAKE, Yoshihiko; NAGAO, Satoshi; KANADA SONABE, Regina, Mikie; MIYANO, Masayuki; MURAI, Norio; BUONAMICI, Silvia; YU, Lihua; PARK, Eunice, Sun; CHAN, Betty; SMITH, Peter, G.; THOMAS, Michael P.; PAZOLLI, Ermira; LIM, Kian, Huat; (54 pag.)WO2017/87667; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 770-08-1, 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. 770-08-1, name is 5-Ethylpicolinic acid, molecular formula is C8H9NO2, 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.

Example IV; Preparation of [1-(6-trichloromethylpyridin-3-yl)ethyl](methyl)-oxido-lambda4-sulfanylidenecyanamide (5); A mixture of 5-ethylpyridine-2-carboxylic acid (1.98 g, 13 mmol), phenyl-phosphonic dichloride (2.8 g, 14.3 mmol), phosphorus pentachloride (7.7 g, 32 mmol) was stirred and slowly heated. Once a clear yellow liquid was formed, the mixture was heated to reflux overnight. After cooling, the volatiles were removed under reduced pressure. The residue was carefully poured into saturated sodium carbonate aqueous solution cooled in an ice-water bath. The aqueous phase was then extracted with CH2Cl2 two times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated, and partially purified on silica gel eluted with 10 percent EtOAc in hexane to give 2.7 g of crude product containing both 5-ethyl-2-(trichloromethyl)pyridine and 5-(1-chloro-ethyl)-2-(trichloromethyl)pyridine in an approximate 3:1 ratio (GC data, masses calcd for C8H8Cl3N and C8H7Cl4N [M]+223 and 257 respectively. Found 223 and 257 respectively).

According to the analysis of related databases, 770-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences, LLC; US2010/168177; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13472-85-0, 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.13472-85-0, name is 5-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

A 2.5 M hexane solution of n-butyllithium (23 mL, 58 mmol) was added over 30 minutes to a -78 C. solution of 5-bromo-2-methoxypyridine (10 g, 53 mmol) in ether (120 mL), keeping the temperature below -65 C. The slurry was stirred for 30 minutes, and then trimethylborate (6.1 mL) was added quickly to the reaction solution. Again the temperature was maintained below -65 C. The solution was stirred for 10 minutes, warmed to 15 C. and then cooled to -78 C. Peracetic acid (56 mmol) was added dropwise, while the temperature was kept at or below -65 C. After addition, the reaction was warmed briefly to -50 C., cooled back to -65 C., then stirred at approximately 25 C. overnight. The reaction was quenched with water (100 mL), and then extracted with ether (3*150 mL). The organic portions were combined and washed with aqueous NaHSO3 solution and brine. The organic portions were extracted two times with 2N aqueous NaOH solution. The pooled basic aqueous fractions were washed with Et2O and then acidified with NaHSO4. The product precipitated out as oil; the aqueous mixture was extracted three times with Et2O, the pooled ether fractions were dried with Na2SO4, and stripped of solvent in vacuo. Yielded 3.6 g of a brown solid.

The chemical industry reduces the impact on the environment during synthesis 13472-85-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Brewster, William Kirkland; Klittich, Carla Jean Rasmussen; Balko, Terry William; Breaux, Nneka Tuere; Erickson, William Randal; Hunter, James Edward; Lowe, Christian Thomas; Ricks, Michael John; Siddall, Thomas Lyman; Yerkes, Carla Nanette; Zhu, Yuanming; US2006/89370; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 207799-10-8, 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. 207799-10-8, name is tert-Butyl (4-bromopyridin-2-yl)carbamate, molecular formula is C10H13BrN2O2, 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.

tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160); To a solution of ter/-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0C is added sodium hydride (53 mg, 1.32 mmol, 60% dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 muL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5% citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO combined organic phases are dried over Na2SO4 and purified by column chromatography (70% EtOAc in heptane) to give the title compound. Yield: 240 mg (76%). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).

According to the analysis of related databases, 207799-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; CURIS, INC.; WO2008/57469; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59281-14-0, 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.59281-14-0, name is 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, molecular formula is C13H13NO3, molecular weight is 231.25, as common compound, the synthetic route is as follows.

General procedure: 20 mmol of compound 4 (4a-4f) was weighed into 100 mL of dichloromethane, Then add 0.16 mol of manganese dioxide, The mixed system was heated under reflux at 50 C in a oil bath for 72-96 h, and the TLC spot plate was used to detect the reaction process. After the reaction is over, The manganese dioxide was removed by suction filtration and the solvent 5 was evaporated to give compound 5.

Statistics shows that 59281-14-0 is playing an increasingly important role. we look forward to future research findings about 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one.

Reference:
Patent; Zhejiang Gongshang University; Zhou Tao; Shao Lele; (12 pag.)CN106986819; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 94952-46-2, 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. 94952-46-2, name is 1-(5-Chloropyridin-2-yl)ethanone, molecular formula is C7H6ClNO, 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.

1-(5-Chloropyridin-2-yl)ethanone (238 mg, 1.53 mmol) was dissolved in methanol (10 mL) at50 C. Sodium borohydride (174 mg, 4.5 mmol) was added portionwise and after addition was complete the reaction mixture was stirred at 50 C for 1 h. The solvent was removed,the residue was dissolved in water (10 mL), extracted with ethyl acetate (20 mL x 4) and the solvent evaporated from the combined organic phases to give 1-(5-chloropyridin-2-yl)ethanol as a colourless oil (201 mg, crude).

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 94952-46-2, 1-(5-Chloropyridin-2-yl)ethanone.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BOUILLOT, Anne Marie Jeanne; DENIS, Alexis; LIDDLE, John; WALKER, Ann, Louise; (58 pag.)WO2016/188828; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1603-41-4 ,Some common heterocyclic compound, 1603-41-4, molecular formula is C6H8N2, 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.

2-amino 5-methyl pyridine (5.0 g) was cooled to 5°C and Con. HCI (90 mL) was added. Sodium nitrite (5.16 g) was added portion wise slowly to the reaction mixture in 15 minutes. The reaction mixture was allowed to warm to 30°C and stirred for 1 .5 hours at the same temperature. Cooled the reaction mixture to 5°C and 40percent aqueous sodium hydroxide solution (150 mL) was added and pH adjusted to 13. Extracted the reaction mixture with ethyl acetate (3 x 50 mL) and washed the combined organic layer with brine solution (50 mL). The solution was dried over sodium sulfate and evaporated the solvent under reduced pressure to afford crude compound. The crude product was purified by column (0376) chromatography using 60-120 silica mesh and (10percent to 20percent) ethyl acetate / hexane as eluent to obtain title compound as colorless liquid. Yield: 2.62 g; Purity by HPLC: 99.97percent

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1603-41-4, its application will become more common.

Reference:
Patent; DR. REDDY?S LABORATORIES LIMITED; DAHANUKAR, Vilas Hareshwar; ORUGANTI, Srinivas; RAO, Pallavi; CHAKKA, Ramesh; BAIG, Mohammed Azeezulla; VYALA, Sunitha; SALADI, Venkata Narasayya; PEDDY, Vishweshwar; ELATI, Raviram Chandrasekhar; MOHANARANGAM, Saravanan; RAJ, Gopal; MAMIDIPALLI, Phani; (73 pag.)WO2017/175161; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 874959-68-9, Adding some certain compound to certain chemical reactions, such as: 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride,molecular formula is C5H3BrClNO2S, 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 874959-68-9.

General procedure: To a pyridine (1.5 mL) solution of 5-((1S,2R)-1-amino-2-(6-fluoro-2,3-dimethylphenyl)propyl)-1,3,4-oxadiazol-2(3H)-one monohydrochloride (45 mg) obtained from Reference Example F1, 5-chloro-8-(chlorosulfonyl)-4-methyl-d3-chroman-4-ylacetate (80 mg) obtained in Reference Example E1 was added, and the reaction solution was stirred atroom temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and the obtainedresidue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain the title compound(59 mg) as a 1: 1 diastereomer mixture.

According to the analysis of related databases, 874959-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; MIYAHARA, Seiji; UENO, Hiroyuki; HARA, Shoki; OGINO, Yoshio; (203 pag.)EP3466934; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem