Tag: M.W:200-300

Synthetic Route of 6945-67-1, Adding some certain compound to certain chemical reactions, such as: 6945-67-1, name is 2-Bromo-4-nitropyridine,molecular formula is C5H3BrN2O2, 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 6945-67-1.

The crude title compound from Step A above was dissolved in a mixture of degassed 1,4- dioxane (8.6 mL) and water (2 mL) in a microwave vial. Then [1 ,1 – bis(diphenylphosphino)ferrocene]dichloro-palladium(ll), complex with dichloromethane (0.034 g, 0.04 mmol), 2-bromo-4-nitropyridine (0.1 g, 0.49 mmol) and cesium carbonate (0.266 g, 0.82 mmol) were added and the reaction mixture was heated at ~115C in a sand- bath for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (30 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford a mixture of the title compound and byproducts (0.076 g).

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. 6945-67-1, 2-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AC IMMUNE S.A.; PIRAMAL IMAGING SA; KROTH, Heiko; MOLETTE, Jerome; DARMENCY, Vincent; SCHIEFERSTEIN, Hanno; MUeLLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; ODEN, Felix; GABELLIERI, Emanuele; (93 pag.)WO2018/15549; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 28733-43-9, 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. 28733-43-9, name is 5-Bromonicotinamide, molecular formula is C6H5BrN2O, 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.

Bromine (18.76 g, 117.4 mmol) was added to a solution of sodium hydroxide (23.88 g, 597 mmol) in water (200 mL). To this solution was added 5-bromonicotinamide (20.00 g, 99.49 mmol). The reaction mixture was heated to 75 C. for 45 minutes. The reaction was cooled and acidified with concentrated hydrochloric acid. Some insoluble material was present. The insolubles were removed by filtration. The solution was washed with ethyl acetate (150 mL, 2 times). The aqueous solution was basified with sodium hydroxide solution (pH 10). The mixture was extracted into ethyl acetate (200 mL, 2 times). The ethyl acetate was dried and condensed to yield compound A (10.07 g, 58.5% yield).

According to the analysis of related databases, 28733-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2009/170886; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 132195-42-7, 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 132195-42-7, name is 2,6-Dichloro-5-fluoro-4-methylnicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A solution of EXAMPLE 1A (9.48 mmol) in dichloromethane (20 mL) was treated with oxalyl chloride (8 mL) and DMF (2 drops), stirred for 1 hour, and concentrated; and the concentrate was dissolved in THF (25 mL) to provide an acid chloride solution. A slurry of the mono-potassium salt of ethyl malonate (4.0 g) in acetonitrile (40 mL) at 0 C. was treated with triethylamine (3.3 mL) and magnesium chloride (3.2 g), warmed to ambient temperature, stirred for 4 hours, treated with the acid chloride solution, stirred for 1 hour, treated with 1M HCl, and extracted with ethyl acetate. The extract was washed with brine, dried (Na2SO4), filtered, and concentrated; and the concentrate was flash chromatographed on silica gel with 90:10 hexanes/ethyl acetate.

According to the analysis of related databases, 132195-42-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anderson, David; Beutel, Bruce; Bosse, Todd D.; Clark, Richard; Cooper, Curt; Dandliker, Peter; David, Caroline; Gu, Yu-Gui; Hansen, Todd Matthew; Hinman, Mira; Kalvin, Douglas; Larson, Daniel P.; Lynch, Linda; Ma, Zhenkun; Motter, Christopher; Palazzo, Fabio; Rosenberg, Teresa; Rehm, Tamara; Sanders, William; Tufano, Michael; Wagner, Rolf; Weitzberg, Moshe; Yong, Hong; Zhang, Tianyuan; US2003/232818; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 91678-23-8 , The common heterocyclic compound, 91678-23-8, name is 2-Bromo-6-chloro-3-nitropyridine, molecular formula is C5H2BrClN2O2, 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.

Under nitrogen a solution of 2-bromo-6-chloro-3-nitropyridine (2.5 g, 10.53 mmol, 1.00 equiv) in THF (60 mL) was cooled to -78 C and bromo(ethenyl)magnesium (1M in THF, 63 mL, 6 equiv) was added dropwise. The reaction was stirred for 1 h at -50 C, quenched with aqueous ammoniumchloride, extracted with ethyl acetate, dried over sodium sulfate, and concentrated in vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3). This resulted in the title compound (1.3 g, 53%) as a yellow solid. LC-MS (ES, m/z):231 [M+H].

The synthetic route of 91678-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083057-12-8 , The common heterocyclic compound, 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, molecular formula is C17H19NO2, 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.

13 g of tert-butyl-3(3-methylpyridin-2-yl)benzoate was dissolved in 80 ml ethyl acetate, then 4 ml water and 15 g ureahydrogen peroxide were added. 22 g of phthalic anhydride was added portion wise and the reaction temperature was maintained below 45 C. Thereaction mixture was heated to 45 C and stined for 4 hours. After completion of reaction, the reaction mass was cooled to room temperature. 100 ml of 10% sodium sulphite solution was added slowly and the reaction mixture was stined for 30 minutes. The layers were separated and organic layer was washed with 100 ml 10% sodium carbonate and 100 ml 10% sodium chloride solution. The organic phase is then filteredand concentrated under vacuum to afford 2-(3-(tert-butoxycarbonyl)phenyl)-3- methylpyridine-1-oxide (13 g, 94.8 %).

The synthetic route of 1083057-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MYLAN LABORATORIES LIMITED; ATTANTI, Veera Venkata Srinivasa Rao; TUMMALAPALLI, Umasankara Sastry; POTLA, Murali Krishna; TALATALA, Appireddy; GOSULA, Veera Venkata Satya Surya Appala Narasimha Tataji; KOMMARAJU, Srinivas; (45 pag.)WO2017/17696; (2017); 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. 929617-30-1, name is 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine. A new synthetic method of this compound is introduced below., Product Details of 929617-30-1

Into a 30 mL sealed tube was placed 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine (900 mg, 4.24 mmol), Pd(dppf)CI2 (315 mg, 0.43 mmol), KOAc (1.25 g, 12.7 mmol) and N,N- dimethylformamide (10 mL). This was followed by the addition of methanol (10 mL) and CO gas. The solution was stirred for 1 h overnight at 80C in an oil bath. The mixture was concentrated under vacuum. The residue was purified over a silica gel column with dichloromethane/methanol (20:1). This resulted in 0.60 g (74%) of methyl 3-methyl-1H- pyrazolo[3,4-c]pyridine-5-carboxylate as a brown solid.

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, 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LTD.; SCHIEMANN, Kai; MALLINGER, Aurelie; (147 pag.)WO2016/26549; (2016); A1;,
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.851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-4-chloro-2-methoxypyridine

To a solution of cyclopropylmethanol (446 mg, 6.18 mmol) in THF (10 mL) was added NaH (247 mg, 6.18 mmol, 60% in mineral oil) in one portion at 0 C. The reaction mixture was warmed up to 20 C. over a period of 30 mins and stirred at 20 C. for 10 mins. Then 5-bromo-4-chloro-2-methoxypyridine (550 mg, 2.47 mmol) was added in one portion and the mixture was stirred at 70 C. for 4 hours. The mixture was diluted with saturated ammonium aqueous solution (50 mL) and extracted by EtOAc (2*30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product which was purified by silica gel column chromatography (PE:EA=20:1 to 10:1) to afford the title compound (450 mg, 70.6%) as colorless oil. 1H NMR: (CDCl3, 400 MHz) delta: 8.11 (s, 1H), 6.18 (s, 1H), 3.90 (s, 3H), 3.89-3.88 (m, 2H), 1.39-1.27 (m, 1H), 0.70-0.67 (m, 2H), 0.46-0.43 (m, 2H). LCMS (M+H)+=258.0 (M+1)+; 260.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,851607-27-7, 5-Bromo-4-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kaldor, Stephen W.; Stafford, Jeffrey Alan; Veal, James Marvin; US2015/111885; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1231930-13-4 , The common heterocyclic compound, 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine, molecular formula is C6H5BrN2O2, 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 Example C7 (1.185 g, 3.93 mmol), Example A6 (0.746 g, 2.81 mmol), K2CO3 (1.165 g, 8.43 mmol) and Pd(PPh3)4 (0.325 g, 0.281 mmol) in dioxane (11 mL) and water (3 mL) was sparged with Ar and heated at 90 C. overnight. The mixture was cooled to RT, treated with EtOAc and brine and the solids removed via filtration through diatomaceous earth. The layers of the filtrate were separated, the aqueous layer extracted with additional EtOAc (3*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 2-methyl-3-((2-(4-(1-methylpiperidin-4-yl)phenyl)pyridin-4-yl)oxy)-6-nitropyridine (553 mg, 49%). MS (ESI) m/z: 405.2 (M+H+).

The synthetic route of 1231930-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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: tert-Butyl (2-methoxypyridin-3-yl)carbamate, blongs to pyridine-derivatives compound. Recommanded Product: tert-Butyl (2-methoxypyridin-3-yl)carbamate

49. Preparation of t-Butyl N-(4-Fluoro-2-methoxy-3-pyridinyl)carbamate To a solution of 8 g (35.7 mmol) of t-butyl N-(2-methoxy-3-pyridyl)carbamate in 200 mL of dry tetrahydrofuran was added with stirring at -60 C., 46.2 mL (78.5 mmol) of 1.7M t-butyl lithium in pentane. The resulting solution was allowed to warm slowly with stirring to -20 C. over a 20 to 30 min period. It was then cooled to about -60 C. and 12.2 g (38.7 mmol) of N-fluorodibenzenesulfonimide was added with stirring all at once. The mixture was allowed to warm to -20 C. and was poured into 500 mL of ether. The resulting ethereal solution was washed with a mixture of 2.5 g (41.7 mmol) of acetic acid and 150 mL of water. The aqueous phase was extracted with 200 mL of ether. The ethereal extracts were combined, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by flash chromatography to obtain 6.7 g (77 percent of theory) of the title compound as a colorless solid melting at 75-77 C. Elemental Analysis C11 H15 FN2 O3 Calc.: %C, 54.5; %H, 6.24; %N, 11.6 Found: %C, 54.2; %H, 6.39; %N, 11.4 1 H NMR (CDCl3): 7.88 (dd, 1H, j=5.8, 7.6); 6.68 (dd, 1H, j=5.8, 8.9); 5.9 (br, 1H); 3.9 (s, 3H); 1.45 (s, 9H).

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DowElanco; US5571775; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1, 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.1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, molecular formula is C7H5BrFNO, molecular weight is 218.02, as common compound, the synthetic route is as follows.

Step 4. (R,E)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide To a solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (10.93 g, 50.1 mmol) in THF (100 ml) was added (R)-(+)-2-methyl-2-propanesulfinamide (12.15 g, 100 mmol) and titanium (IV)-ethoxide (20.75 mL, 100 mmol). The resulting mixture was then heated at reflux for 1 h. The mixture was cooled to RT and brine (300 mL) was added. The mixture was stirred at RT for 15 min, then filtered and the solid was washed with DCM (2*100 mL). The organic layer was collected and the aqueous layer was dried over MgSO4 and concentrated. The residue was then dissolved in DCM (10 mL) and purified by silica gel chromatography, eluent 0%-100% EtOAc/hexane, to give 14.9 g of the title compound as a yellow solid. MS (ESI, positive ion) m/z: 321, 323 (M+H).

Statistics shows that 1111637-74-1 is playing an increasingly important role. we look forward to future research findings about 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem