Tag: M.W:200-300

Synthetic Route of 58236-70-7, 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. 58236-70-7, name is 5-Bromo-3-chloropyridin-2(1H)-one, molecular formula is C5H3BrClNO, 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.

36.0 g (172.7 mmol) of 5-bromo-3-chloro-2-hydroxypyridine are stirred at 160° C. for 6 hours in 320 ml of phosphorus tribromide. The reaction mixture is cooled to room temperature and poured carefully into ice water. After 2 hours, the mixture is extracted three times with 500 ml of dichloromethane in each case. The combined organic phases are washed with sodium bicarbonate solution until neutral, dried over Na2 SO4 and filtered, and the filtrate is evaporated to dryness. Chromatographic purification (silica gel/dichloromethane) gives 20.53 g of 3-chloro-2,5-dibromopyridine. STR14 m.p.: 40°-41° C.

According to the analysis of related databases, 58236-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoechst Aktiengesellschaft; US5629428; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 29241-65-4 ,Some common heterocyclic compound, 29241-65-4, molecular formula is C6H3BrClNO2, 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.

Sulfuric acid (2 mL, 52.1 mmol) was added to the suspension of 5-bromo-2-chloronicotinic acid (1) (12.3 g, 52 mmol) was in methanol (100 mL). The mixture was stirred and refluxed for 15 hours. The solvent was evaporated and the residue was neutralized with saturated aqueous NaHC03(aq.). The result suspension was filtered and the solid was washed by water and dried by pump. Methyl 5-bromo-2-chloronicotinate (2) (11.6 g, 89 % yield) was afforded. NMR (400 MHz, CDCL) delta 8.53 (d, J = 2.4 Hz, 1H), 8.25 (d, J = 2.4 Hz, 1H), 3.93 (s, 3H). 13C NMR (101 MHz, CDCL) delta 163.58, 152.75, 148.61, 142.49, 127.64, 118.57, 53.10. ESI-MS m/z: 251.9 (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. 29241-65-4, 5-Bromo-2-chloronicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; ZHAO, Xue, Zhi; SMITH, Steven; METIFIOT, Mathieu, A.; JOHNSON, Barry; MARCHAND, Christophe; HUGHES, Stephen; POMMIER, Yves; BURKE, Terrence, R.; WO2014/186398; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. A new synthetic method of this compound is introduced below.

Step 1: Synthesis of methyl 3-(6-bromo-4-methylpyridin-2-yl)-3-hydroxycyclobutanecarboxylate A solution of 2,6-dibromo-4-methylpyridine (1.50 g, 5.97 mmol) in DCM (30 mL) was cooled to -78 C., and n-BuLi (2.5 M, 2.60 mL, 6.56 mmol) was added dropwise to the above solution at -78 C. The solution was stirred at -78 C. for another 15 min. Methyl 3-oxocyclobutanecarboxylate (917 mg, 7.16 mmol) was added to the solution, and the resultant mixture was stirred at -78 C. for 30 min. The mixture was then quenched by addition of saturated aqueous NH4Cl solution and extracted with DCM. Organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column (PE:EA=2:1) to give methyl 3-(6-bromo-4-methylpyridin-2-yl)-3-hydroxycyclobutanecarboxylate (1.0 g, 56%) as a white solid, MS (ES+) C12H14BrNO3 requires: 299, found: 300 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73112-16-0, 2,6-Dibromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Kim, Joseph L.; Kevin, Douglas J.; Brubaker, Jason D.; (57 pag.)US2017/267661; (2017); 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. 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, the common compound, a new synthetic route is introduced below. Recommanded Product: 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone

A mixture of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (11 g, 51 mmol), (R)-2-methylpropane-2-sulfinamide (12.2 g, 101 mmol) and titanium (IV) ethoxide (26.1 mL, 126 mmol) in THF (100 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature, brine was added and the mixture was stirred for 10 min. The suspension was filtered through silica gel. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 0-20% EtOAc/hexanes) gave (R,Z)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (16 g, 50 mmol, 99% yield) as a bright yellow oil. LC/MS (ESI) m/z=321 (M+H).

The synthetic route of 1111637-74-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89364-04-5, 3-Bromo-4-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, Recommanded Product: 3-Bromo-4-nitropyridine, blongs to pyridine-derivatives compound. Recommanded Product: 3-Bromo-4-nitropyridine

To a solution of 1,4-dioxane (60mL) and water (10mL) was added 3-bromo-4-nitropyridine (1.02g, 5.0mmol), (4-bromophenyl)boronic acid (1.10g, 5.5mmol), Pd(PPh3)4 (0.23g, 0.2mmol), and Na2CO3 (1.33g, 12.5mmol). Then the reaction was allowed to stir at reflux temperature (110C) for 18h. The reaction was cooled down, poured into water (40mL) and extracted with EtOAc (80mL×3). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in reduced pressure. The residue was purified by silica gel column chromatography using an eluent (10:90 EtOAc/hexanes) to afford a yellow solid product 1 (1.0g, 72%). Rf=0.50 (1:2 EtOAc/hexanes), mp 135-137C. 1H NMR (CDCl3): delta 7.21 (d, J=8.0Hz, 2H, Ph-H), 7.61 (d, J=8.0Hz, 2H, Ph-H), 7.68 (d, J=5.2Hz, 1H, Py-H), 8.78 (s, 1H, Py-H), 8.84 (d, J=5.2Hz, 1H, Py-H). 1H NMR (DMSO-d6): delta 7.41 (dt, J=2.2, 9.0Hz, 2H, Ph-H), 7.71 (dt, J=2.2, 9.0Hz, 2H, Ph-H), 8.03 (d, J=5.5Hz, 1H, Py-H), 8.87 (s, 1H, Py-H), 8.93 (d, J=5.5Hz, 1H, Py-H). MS (ESI): 279 ([M+H]+, 100%).

The synthetic route of 89364-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Mingzhang; Wang, Min; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 25; 15; (2015); p. 2953 – 2957;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 195044-14-5, 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. 195044-14-5, name is 2-Bromo-6-tert-butylpyridine, molecular formula is C9H12BrN, 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.

To a stirred solution of 2-(2-methoxyethyl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (300 mg, 1.248 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (320 mg, 1.497 mmol, 1.2 eq) in dioxane (6 mL) was added potassium carbonate (344.7 mg, 2.496 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (47.53 mg, 0.249 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (44 mg, 0.499 mmol, 0.4 eq) and again purged with nitrogen for 30 min. The resultant mixture was heated at 110 C. for 5 h. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 50% EtOAc/Hexane to afford pure to afford 1-(6-tert-butylpyridin-2-yl)-2-(2-methoxyethyl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3 (2H)-one (200 mg, 42.91%).

According to the analysis of related databases, 195044-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 944445-41-4, 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. 944445-41-4, name is 3-(Benzyloxy)-2-(chloromethyl)pyridine, molecular formula is C13H12ClNO, 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.

Stage B: 3-(Benzyloxy)-2-(methoxymethyl)pyridine The solution of 41 g (0.18 mol) of 3-(benzyloxy)-2-(chloromethyl)pyridine in 100 ml of methanol is added to the solution of sodium methoxide, prepared by adding 5.2 g (0.23 mol) of sodium to 150 ml of methanol. After refluxing for 3 hours under nitrogen, the solution is concentrated to dryness. The oil obtained is taken up in water and extracted with ethyl acetate. The organic solution is washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulphate, and then concentrated to dryness. 39 g (97%) of a brown oil are obtained. 1H-NMR [(CD3)2SO, 250 MHz]: 8.15 (1H, d), 7.30-07.55 (7H, m), 5.22 (2H, s), 4.55 (2H, s), 3.31 (3H, s).

According to the analysis of related databases, 944445-41-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2009/69368; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 57883-25-7, 3-Bromo-2-ethoxypyridine, 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, Product Details of 57883-25-7, blongs to pyridine-derivatives compound. Product Details of 57883-25-7

To a solution of 3-bromo-2-ethoxy-pyridine (350 mg, 1.7 mmol) in NMP (2 mL) was added Zn(CN)2 (244 mg, 2.1 mmol) and Pd(dppf)Cl2 (127 mg, 0.17 mmol). The mixture was degassed with N2 and heated at 140 C. under microwave irradiation for 1 hour. The mixture was cooled to room temperature and filtered through celite. The filtered cake was washed with ethyl acetate (30 mL). The filtrate was washed with water (20 mL*2) and brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (0%?20% ethyl acetate in petroleum ether) to give 2-ethoxynicotinonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57883-25-7, 3-Bromo-2-ethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; US2019/185489; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, 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, Quality Control of N-(4-Bromopyridin-2-yl)acetamide, blongs to pyridine-derivatives compound. Quality Control of N-(4-Bromopyridin-2-yl)acetamide

1001161 To a mixture of N-(4-bromopyridin-2-yl)acetamide (17.2 g, 80 mmol), 4,4,4,4,5,5,5,5- octamethyl-2,2-bi-1,3,2-dioxaborolane (26.4 g, 104 mmol), Pd(dppf)C12 (11.7 g, 16 mmol) and KOAc (23.6 g, 240 mmol) under an atmosphere of nitrogen was added anhydrous DMF (1500 mL). The mixture was allowed to stir at 80 C for 3.5 h. The solvent was removed and the residue was diluted with EtOAc (1000 mL). Activated carbon (100 g) was added. The slurry was heated at reflux for 5 mm and then filtered. The organic solution was concentrated and the residue was recrystallized from EtOAc to give N[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (6.1 g, 29%) as a white solid. ?H NMR (400 MHz, DMSO-d6): 1.29 (s, 12H), 2.09 (s, 3H), 7.24 (dd, J= 6.0, 1.2 Hz, 1H), 8.30-8.33 (m, 2H), 10.47 (br s, 1H).

The synthetic route of 1026796-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; XU, He; YE, Yingchun; WO2015/108881; (2015); 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. 637348-81-3, name is 3-Bromo-5-iodopyridin-2-ol, the common compound, a new synthetic route is introduced below. COA of Formula: C5H3BrINO

To a stirring suspension of 18 (see Example 4 above) (0.906 g, 3.0 mmol), 2-(tert-butyl-dimethyl-silanyloxy)ethanol (0.554 g, 3.15 mmol) and PPh3 (0.944 g, 3.6 mmol) in 20 mL of THF at -10 0C was added dropwise of diisopropylazodicarboxylate (DIAD) (0.728 g, 3.6 mmol) in 10 mL of THF. The ice-salt bath was removed and the reaction was kept at r.t. 2 h. The reaction solution was concentrated and purified by FC (EtOAc/Hexanes, 5/95) to afford 2-(tert-butyl-dimethyl-siianyloxy)ethoxy-3-bromo-5-iodorhoyridine, a colorless viscous liquid (0.995 g, 72%). 1H NMR £8.23 (d, IH, J= 2.0 Hz), 8.05 (d, IH, J= 2.0 Hz), 4.42 (t, 2H, J= 4.9 Hz), 3.98 (t, 2H, J= 4.9 Hz), 0.90 (s, 9H), 0.10 (s, 6H). HRMS calcd for C12H18BrINO2Si (M-CH3+), 441.9335; found, 441.9312.

The synthetic route of 637348-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; WO2007/126733; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem