Day: February 8, 2021

Related Products of 22245-83-6 , The common heterocyclic compound, 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol, molecular formula is C6H4F3NO, 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 mixture of 3- (trifluoromethyl) pyridin-2-ol (2 g 12.26 mmol) was added nitric acid (1.644 mL 36.8 mmol) and H2SO4(12.03 g 123 mmol) at 0 . Then the mixture was stirred at 25 for 16 h. The mixture was then warmed to 60 for 5 h cooled and added to 150 g of ice. The mixture was extracted with EA (2 x 100 mL) and washed with H2O (100 mL) to give the organic layer. The combined organic extract was washed with brine dried over Na2SO4 concentrated to yield a brown solid of 5-nitro-3- (trifluoromethyl) pyridin-2-ol (2.2 g 8.99 mmol 73.3yield) 1HNMR(400 MHz CD3OD) delta 8.91 (d J 2.43 Hz 1H) 9.42 (d J 2.43 Hz 1H) ES-LCMS m/z 209.0 (M+H)

The synthetic route of 22245-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 850663-54-6, 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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one, molecular formula is C5H3ClN2O3, 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.

Step 3.2, 4-Dichloro-5-nitropyridine The product from Step 2 (40.0 g, 229 mmol) was suspended in toluene (300 mL) and POC13 (65 mL, 697 mmol) was added over 10 min, then the mixture was heated to relux for 6 h then cooled to 60 C and allowed to stir overnight at that temperature. The heterogeneous mixture was cooled and concentrated, the residue was carefully made basic with aq. K2CO3 solution and extracted with EtOAc. The organic layers were combined, washed with H20 and brine, dried (Na2S04), filtered and the filtrate was concentrated to give an oil. The crude oil was passed through a plug of silica gel (50% EtOAc in hexanes) to give the title compound (32.5 g, 74 %) as an orange oil which solidified on standing. MS (ES+) m/e 194 [M+H] +.

According to the analysis of related databases, 850663-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/37197; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55717-45-8 ,Some common heterocyclic compound, 55717-45-8, molecular formula is C5H4BrNO, 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 benzylbromide (3.24g, 18.97mmol), 6-bromopyridin-3-ol (3g, 17.24mmol) and cesium carbonate (8.43 g, 25.90 mmol) in dry acetonitrile (50 mL) was stirred overnight at room temperature. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate (80 mL) and filtered. The filtrate was concentrated under vacuum to afford the title compound (4.05 g). Yield: 89% JH NMR (300 MHz, CDCI3): delta 8.15 (s, 1H), 7.42-7.37 (m, 5H), 7.19-7.15 (m, 1H), 5.11 (s, 2H).

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. 55717-45-8, 6-Bromopyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; KUMAR, Sanjay; SHARMA, Rajiv; DEORE, Vijaykumar, Bhagwan; YEWALKAR, Nilambari Nilkanth; (119 pag.)WO2016/12965; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.7379-35-3, name is 4-Chloropyridine hydrochloride, molecular formula is C5H5Cl2N, molecular weight is 150.0059, as common compound, the synthetic route is as follows.Product Details of 7379-35-3

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) delta5.67 (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; US2004/2508; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 769-54-0, 3-Fluoro-4-nitropyridine 1-oxide, 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: C5H3FN2O3, blongs to pyridine-derivatives compound. Formula: C5H3FN2O3

Under ice-cooling, 3-fluoro-4-nitropyridine 1-oxide (9.75 g, 61.7 mmol) with the eyeThe mixed suspension of ethanol (145 mL), 28% sodium methoxide methanol solution (11.9 g, 61.7 mmol) was added. The temperature was raised to room temperature, the mixture was stirred at the same temperature for 1 hour. Reduced pressure methanolWas distilled off under Water (50 mL) was added and extracted with chloroform to the residue. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was evaporated under reduced pressure to obtain the desired product (9.54 g, 91% yield).

The synthetic route of 769-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA LIMITED; KIRIYAMA, KAZUHISA; JUKUROGI, TATSUYA; UMEMOTO, NAO; KANI, TATSUYA; MATSUDA, YOKO; TANAKA, KUMINO; (64 pag.)JP2016/11294; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98-98-6, 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. 98-98-6, name is Picolinic acid. A new synthetic method of this compound is introduced below.

Description 1; 3-Iodo-2-pyridinecarboxylic acid (D1); To a stirred solution of 2,2,6,6-tetramethylpiperidine (20 ml, 0.122 mol) in dry THF (100 ml) at -78¡ã C., under argon was added n-butyllithium (52 ml, 0.163 mol, 2.5M solution in hexanes) dropwise, followed 15 min later by a solution of 2-pyridinecarboxylic acid (5.0 g, 0.0407 mol) in dry THF (30 ml). After 10 min at -78¡ã C., the reaction mixture was warmed to 0¡ã C. for 30 min. and then transferred to a solution of iodine (30.9 g, 0.243 mol) in dry THF (70 ml) at 0¡ã C., under argon. After 15 min at 0¡ã C. the reaction mixture was warmed to 25¡ã C. and stirred for 1 h. After this period water (80 ml) was added and the reaction mixture concentrated in vacuo. The residue was re-dissolved in water (100 ml) and washed with EtOAc (100 ml). The aqueous layer was separated, concentrated in vacuo and the resulting residue triturated with diethyl ether. The solid material was filtered and dried in vacuo before being re-dissolved in MeOH (200 ml). To this solution was added Amberlyte IR-120 ion-exchange resin (100 g) and the reaction mixture stirred at 25¡ã C. for 2 h. After this period the resin was filtered off and the solvents concentrated in vacuo to afford the title compound (4.15 g, 41percent). deltaH (DMSO-d6, 250 MHz) 6.79 (1H, bs) 7.28 (1H, dd), 8.37 (1H, dd), 8.58 (1H, dd). MS (ES): C6H41NO2 requires 249. found (M-H+) 248.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98-98-6, its application will become more common.

Reference:
Patent; Glaxo Group Limited; US2008/312209; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 849937-96-8, 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 849937-96-8 as follows.

To a solution of 5-bromo-2,4-dichloropyridine (CAS 849937-96-8) (22.95 g, 96.1 mmol, Eq: 1.00) in Toluene (352 mL) and Water (48.0 mL) was added Pd(OAc)2 (431 mg, 1.92 mmol, Eq: 0.02), butyldi-l-adamantylphosphine (1.03 g, 2.88 mmol, Eq: 0.03), potassium cyclopropyltrifluoroborate (CAS 1065010-87-8) (14.9 g, 101 mmol, Eq: 1.05) and Cs2C03 (62.6 g, 192 mmol, Eq: 2.0). The resulting reaction mixture was stirred at 110C overnight and controlled by TLC. The reaction was found to be only partially complete so 0.5 more equivalents (7.5 g) of potassium cyclopropyltrifluororate were added (3 times). Reaction mixture concentrated in vacuo then diluted with ethyl acetate and the solution poured into a separatory funnel. Extraction with aqueous saturated NaHC03, organic phase dried over NaS04 and evaporated down to dryness. Flash chromatography with a 330 g Si02 column, eluent mixture of heptane and ethyl acetate giving 7.39 g of the desired product (Yield 40%). MS (ESI, m/z): 188.2 (M).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,849937-96-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GAVELLE, Olivier; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; ROMBACH, Didier; SCHULZ-GASCH, Tanja; WO2014/154612; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 62226-17-9, name is 4-Chlorothieno[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. Formula: C7H4ClNS

To a 100 ml three-necked flask was added 4-chlorothiophene [2,3-b]pyridine (5 g, 0.029 mol), Acetic acid (20 ml), bromine (9.28 g, 0.058 mol) was added dropwise at room temperature. After the completion of the dropwise addition, the reaction was carried out for 18 hours, and after the TLC monitoring reaction was completed, a saturated sodium sulfite solution was added.The mixture was extracted with EtOAc. The concentrated solvent was purified by silica gel column chromatography to afford Intermediate int9 (6.319 g, yield 87%).

The synthetic route of 62226-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Haichuang Pharmaceutical Co., Ltd.; Fan Lei; Du Wu; Xu Kexin; Chen Ke; Wang Fei; Wu Xiaoquan; Luo Tongchuan; Zhang Shaohua; Li Xinghai; Chen Yuanwei; (67 pag.)CN108659000; (2018); A;,
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. 1033201-61-4, name is 6-Amino-3-bromopicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Amino-3-bromopicolinic acid

A slurry of 6-amino-3-bromopicolinic acid (25 g) in 400 mL 1:1dichloromethane/chloroform was added to nitrosonium tetrafluoroborate (18.2 g) in dichloromethane(100 mL) at 5 oc over 1 hour. The resulting mixture was stirred for another 30 minutes, then warmed30 to 35 oc and stirred overnight. The reaction was cooled to room temperature, and then adjusted to pH4 with aqueous NaH2P04 solution. The resulting solution was extracted three times withdichloromethane, and the combined extracts were washed with brine, dried over sodium sulfate,filtered and concentrated to provide the title compound

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, 1033201-61-4, 6-Amino-3-bromopicolinic acid.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; SOUERS, Andrew, J.; PHILLIPS, Andrew, C.; JUDD, Andrew, S.; BRUNCKO, Milan; (717 pag.)WO2017/214282; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113118-81-3 ,Some common heterocyclic compound, 113118-81-3, molecular formula is C6H4BrNO, 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.

Steps 1 (0824) To a mixture of 5-bromopyridine-3-carbaldehyde (XXXVIII) (6.00 g, 32.26 mmol, 1.0 eq), 3,3-difluoropyrrolidine (5.56 g, 38.71 mmol, 1.20 eq) and TEA (5.39 mL, 38.71 mmol, 1.2 Eq) in DCE (200 mL) was stirred at room temperature for 30 min, then added sodium triacetoxyborohydride (10.25 g, 48.38 mmol, 1.50 eq) in one portion at room temperature under N2. The mixture was stirred at room temperature for 6 hours. TLC showed the reaction was complete. The reaction was quenched with 1N NaOH (100 mL), extracted with DCE (100 mL¡Á2). The combined organic layers were washed with brine (100 mL), dried and concentrated. The residue was purified by silica gel chromatography (column height: 50 mm, diameter: 50 mm, 300-400 mesh silica gel, DCM/MeOH=30/1?20/1) to give 3-bromo-5-((3,3-difluoropyrrolidin-1-yl)methyl) pyridine (XL): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). 1H NMR (CDCl3, 400 MHz) delta ppm 2.30 (spt, J=7.2 Hz. 2H), 2.75 (t, J=6.8 Hz, 2H), 2.91 (t, J=13.2 Hz, 2H), 7.85 (s, 1H), 8.45 (s, 1H), 8.59 (d, J=2 Hz, 1H); ESIMS found for C10H11BrF2N2 m/z 277.0 (M+H).

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. 113118-81-3, 5-Bromonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (268 pag.)US2016/68529; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem