Tag: M.W:200-300

Application of 13958-99-1, 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. 13958-99-1, name is 3-Bromoisonicotinamide. A new synthetic method of this compound is introduced below.

3- Bromo-4-cyanopyridine (34). 3-Bromopyridine-4-carboxamide98 (687 mg, 3.4 mmol) was added to phosphorus oxychloride (5.0 ml_) at 0C. The mixture was then stirred at reflux for 2 h. The mixture was cooled, poured onto ice (100 g) with stirring and was neutralised with aqueous sodium hydroxide (5 M, 60 ml_). The mixture was extracted with diethyl ether (2 chi 50 mL). The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate, treated with charcoal and filtered. The solvent was evaporated. The solid was recrystallised from petroleum ether to give 34 (292 mg, 42%) as an off-white powder: mp 79-81 C (lit.99 mp 96.6-98.2C); 1H NMR (CDCI3) delta 7.53 (1 H, d, J = 4.9 Hz, 5-H), 8.69 (1 H, d, J = 4.9 Hz, 6-H), 8.92 (1 H, s, 2- H); 13C NMR (CDCI3) (HSQC / HMBC) delta 1 14.79 (C?N), 122.14 (4-C), 124.17 (3-C), 126.75 (5-C), 148.76 (6-C), 152.69 (2-C); MS (ESI) m/z 182.9552 (M + H) (C6H4N279Br requires 182.9541).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13958-99-1, its application will become more common.

Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1017793-20-2 , The common heterocyclic compound, 1017793-20-2, name is 2,5-Difluoro-4-iodopyridine, molecular formula is C5H2F2IN, 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 solution of Example 5A (100 mg, 0.234 mmol) and 2,5-difluoro-4-iodopyridine (200 mg, 0.830 mmol) in 3.5 mL of 1 ,2-dimethoxyethane was added 1.5 mL saturated sodium bicarbonate solution and the mixture was degassed with nitrogen. 1 , 1 ‘-Bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (33.9 mg, 0.041 mmol) was added and the mixture was heated at 100C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The combined organic layers were washed with water and brine (25 mL each) and dried over sodium sulfate. Filtration, concentration and purification by column chromatography (silica gel, 50% ethyl acetate-hexane) afforded the title compound. LCMS: 415.4 (M+H)+.

The synthetic route of 1017793-20-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 909720-21-4, 2,3-Dibromo-6-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, SDS of cas: 909720-21-4, blongs to pyridine-derivatives compound. SDS of cas: 909720-21-4

1,4-Dioxane (450 mL) and water (150 mL) were added to a mixture of 2,3- dibromo-6-methoxypyridine (12 g, 45 mmol), C2 (31.8 g, 135 mmol), di(l -adamantyl)- ?- butylphosphine (cataCXium A; 3.22 g, 8.98 mmol), palladium(ll) acetate (3.03 g, 13.5 mmol), and cesium carbonate (87.9 g, 270 mmol), and the reaction vessel was evacuated and charged with nitrogen. This evacuation cycle was repeated twice, and the reaction mixture was then stirred at reflux for 20 hours. After the reaction mixture had been partitioned between ethyl acetate (300 mL) and saturated aqueous sodium chloride solution (200 mL), the aqueous layer was extracted with ethyl acetate (2 x 200 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was treated with triethylamine (3 mL), dissolved in dichloromethane and treated with silica gel; this mixture was concentrated to dryness and used for silica gel chromatography (Gradient: 0% to 6% ethyl acetate in petroleum ether) to afford the product as a brown oil. Yield: 10 g, 27 mmol, 60%. LCMS m/z 388.0 [M+Na+]. 1H NMR (400 MHz, CDCI3) delta 7.39 (d, J=8.3 Hz, 1H), 6.52 (d, J=8.3 Hz, 1H), 4.63 (dd, J=4.0, 2.8 Hz, 1H), 4.58 (dd, J=4.0, 2.8 Hz, 1H), 4.19-4.1 1 (m, 1H), 3.94-3.71 (m, 4H), 3.89 (s, 3H), 3.58-3.42 (m, 3H), 3.05 (t, J=7.2 Hz, 2H), 2.89 (t, J=7.2 Hz, 2H), 1.86-1.74 (m, 2H), 1.74-1.64 (m, 2H), 1.62-1.44 (m, 8H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,909720-21-4, 2,3-Dibromo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; HENDERSON, Jaclyn Louise; YOUNG, Joseph Michael; WAGER, Travis T.; KORMOS, Bethany Lyn; PATEL, Nandini Chaturbhai; SCIABOLA, Simone; TUTTLE, Jamison Bryce; VERHOEST, Patrick Robert; TUCKER, Joseph Walter; (181 pag.)WO2017/122116; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 98027-84-0, 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. 98027-84-0, name is 2,6-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, 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.

A mixture of 2,6-dichloro-4-iodopyridine (40 g, 146 mmol), benzenethiol (16.4 mL, 160 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (8.45 g, 14.6 mmol), and diisopropylethylamine (48.3 mL, 292 mmol) in dioxane (600 mL) was flushed with N2 for 5 min before tris(dibenzylideneacetone)dipalladium (0) (6.69 g, 7.30 mmol) was added and the resulting mixture stirred at 110C for 90 min. The resulting suspension was concentrated in vacuo and purified by flash chromatography, eluting with DCM (0 – 40 %) in heptane to yield the title compound as a white solid (28.8 g, 77 ). 1H NMR (500 MHz, DMSO-d6) delta 8.01- 7.39 (m, 5 H), 7.06 (s, 2 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 98027-84-0, 2,6-Dichloro-4-iodopyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 624-28-2, 2,5-Dibromopyridine, 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, 624-28-2, blongs to pyridine-derivatives compound. Computed Properties of C5H3Br2N

To a stirred solution of 2,5-dibromopyridine (1.0 g, 4.2 mmol) in tert-butanol (5 ml) was added (S)-3-hydroxypyrrolidine (0.74 g, 8.44 mmol; Aldrich) and sodium carbonate (1.34 g, 12.70 mmol). The mixture was heated at 140 C. for 3 hours in a reacti-vial. After cooling to room temperature the mixture was diluted with water (20 ml) and extracted with ethyl acetate (20 ml). The aqueous component was separated and extracted with ethyl acetate (20 ml). The combined organic components were dried (Na2SO4), filtered and concentrated to give a brown oil. The crude product mixture was purified by column chromatography (eluding with 100% DCM?90:10:1 DCM:MeOH:NH3) to give the desired product as a white solid (1.0 g, 97%). 1H NMR (400 MHz, CDCl3) delta ppm 2.01-2.20 (m, 3H), 3.41-3.60 (m, 4H), 4.58-4.61 (m, 1H), 6.23 (d, 1H), 7.45 (dd, 1H), 8.11 (d, 1H). LRMS m/z (APCI) 377 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,624-28-2, its application will become more common.

Reference:
Patent; Pfizer Inc; US2008/85884; (2008); 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. 65515-28-8, name is Methyl 2,6-dichloronicotinate, the common compound, a new synthetic route is introduced below. Product Details of 65515-28-8

A solution of 4-chlorophenol (12.2 g, 0.095 mol) in 36.6 mL of DMF was added at room temperature to the above solution (19.6 g of ester 2, 0.095 mol), followed by addition of triethylamine (17.3 mL, 0.124 mol) at 20-22 0C over 15 min. Solid DABCO (1.6 g, 14.2 mmol) was added to the resulting solution in one portion. A temperature increase of ~3 0C was observed. A water bath was used to maintain the reaction temperature. The reaction was stirred at 22-24 0C for 4-5 h while monitoring by LC until all of the 4- chlorophenol was consumed, resulting in a light slurry. AcOH (2.72 mL, 47.5 mmol) and IPA (57.5 mL) were added to the light slurry, followed by cold water (30 mL) to maintain the internal temperature at 20-25 0C. When the water was added, a clear solution first formed, and then a slurry of product formed. After stirring at RT for 0.5 h, additional water (86 mL) was added over 0.5 h. After the slurry was stirred at RT for 1-2 h, it was filtered. The filter cake was washed with mixed solvents (60 mL OfIPAiH2O = 1:1). The isolated solid was dried in a vacuum-oven at 50 0C for 8 h to provide the product as white cotton-like solid.

The synthetic route of 65515-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/96564; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 39856-50-3 ,Some common heterocyclic compound, 39856-50-3, molecular formula is C5H3BrN2O2, 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 a nitrogen purge, the solid 4-bromo-2-nitropyridine (10. Ig; 0.05mol), potassium carbonate (10.5g; 0.075mol; -325mesh), tetrabutylammonium iodide (1.25g; 5mol%), and piperazine (5.4g; 0.0625mol) were sequentially added to 80ml acetonitrile. The suspension was heated to reflux, and maintained for 16 h. The now-bright yellow suspension was filtered hot, and the filter cake washed with a few portions of hot acetonitrile, such that the filtrate flows only slightly yellow. The filtrate quickly deposited a yellow/orange solid. This was reheated to obtain a clear solution, which was placed in the refrigerator for 16 h. The yellow/orange solid was isolated by filtration and the filter cake was washed with small portion cold CH3CN, followed by a small portion of petroleum ether. Air drying the solid provided ca 10.2g of solid material, about 65% of theory. Another 2g of material was isolated by evaporating the acetonitrile filtrate down to a semi-solid and then recrystallizing the residue from a minimum amount of hot isopropanol (treated with activated charcoal). NMR: 1.63 (s, IH), 2.99 (m, 4H), 3.36 (m, 4H), 7.14 (m, IH), 8.08 (m, 2H), m/z 209.

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. 39856-50-3, 5-Bromo-2-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/95159; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884495-39-0, 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 884495-39-0 as follows.

5-Bromo-2-methoxypyridin-3-amine (1 .73 g, 6.82 mmol) was dissolved in 50 mL dioxane. Bis(pinacolato)diboron (4.4 g, 17.33 mmol) and potassium acetate (2.5 g, 25.47 mmol) were added and the mixture was submitted to three vacuum-argon cycles. Then bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.9 g, 0.16 mmol) was added under argon conditions and the mixture heated at 80C for 2h. The reaction mixture was partitioned between ethyl acetate and water and filtered through a plug of celite. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1Purification System (0% to 20%, hexane-ethyl acetate) to obtain 1 .43g. This solid was triturated with hexane, filtered and dried in the vacuum oven to give 0.94 g (55% yield) of the desired product as a solid. Purity 100%.LRMS (m/z): 251 (M+1 )+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-39-0, its application will become more common.

Reference:
Patent; ALMIRALL, S.A.; ERRA SOLA, Montserrat; CARRASCAL RIERA, Marta; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; BERNAL ANCHUELA, Francisco Javier; PAGES SANTACANA, Lluis Miquel; MIR CEPEDA, Marta; CASALS COLL, Gaspar; HERNANDEZ OLASAGARRE, Maria Begona; WO2014/60432; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 832735-56-5, 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.832735-56-5, name is 4-Bromo-2-(difluoromethoxy)pyridine, molecular formula is C6H4BrF2NO, molecular weight is 224.0029, as common compound, the synthetic route is as follows.

A solution of 4-bromo-2-(difluoromethoxy)pyridine (1.25 g, 5.56 mmol) in 1,4-dioxane (30 mL) was added to Pd(dppf)Cl2(406 mg, 0.56 mmol), B2Pin2(1.55 g, 6.10 mmol) and KOAc (1.2 g, 12.2 mmol) under N2 and the reaction was heated to reflux for 22 h. The mixture was filtered through celite and concentrated in vacuo to afford the crude title compound (2.57 g) which was used without further purification.LCMS m/z 271.8 (M+H)+(ES+).1H NMR (DMSO-d6): d 8.28 (d, J = 4.9 Hz, 1H), 7.70 (t, J = 72.9 Hz, 1H), 7.41 (d, J = 4.8 Hz, 1H), 7.13 (s, 1H), 1.29 (s, 12H).

The chemical industry reduces the impact on the environment during synthesis 832735-56-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INFLAZOME LIMITED; MILLER, David; MACLEOD, Angus; THOM, Stephen; MCPHERSON, Christopher G.; ALANINE, Thomas; CARRILLO ARREGUI, Jokin; CIANA, Claire-Lise; SHANNON, Jonathan; VAN WILTENBURG, Jimmy; DEN HARTOG, Jacobus Antonius Joseph; (603 pag.)WO2019/211463; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1017789-38-6, name is tert-Butyl (4,6-dichloropyridin-2-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C10H12Cl2N2O2

1017789-38-6) (200 mg, 0.760 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (348 mg, 1.67 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.076 mmol), and potassium phosphate tribasic (484 mg, 2.28 mmol) in a flask was evacuated and backfilled with argon three times. Dioxane (3 mL) and water (0.33 mL) were added, and the reaction mixture was heated to 100C for 5 hours. The mixture was allowed to cool to room temperature. Hydrochloric acid (4.0 N in dioxane, 3.80 mL, 15 mmol) was added to the mixture, and the suspension was stirred vigorously for 14 hours at room temperature. The mixture was filtered and concentrated under reduced pressure. The residue was dissolved in DMSO and purified via reverse phase HPLC (15-50% acetonitrile/water with 0.1% TFA, linear gradient) to give 4,6-bis(l -methyl- lH-pyrazol-4-yl)pyridin-2-amine. MS ESI calc’d. for C13H15N6 [M + H]+ 255, found 255. 1H NMR (500 MHz, DMSO-d6) delta 8.46 (s, 1H), 8.42 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.70-7.59 (m, 2H), 7.40 (s, 1H), 6.80 (s, 1H), 3.93 (s, 3H), 3.90 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1017789-38-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DONOFRIO, Anthony; ELLIS, John Michael; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; WO2013/52393; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem