Category: 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., Application In Synthesis of 2,6-Dibromo-4-methylpyridine

A suspension of 2,6-dibromo-4-methylpyridine (2.91 g, 11.6 mmol), pivalic acid (0.25 mL, 2.11 mmol), potassium carbonate (2.92 g, 21.1 mmol), thiazole (0.75 mL, 10.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.49 g, 0.42 mmol) in N,N- dimethylacetamide (23 mL) was heated at 130 C for 18 hours. The reaction mixture was diluted with ethyl acetate, filtered through a pad of CELITE, and washed with water (2x). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/hexanes) to afford 2-bromo- 4-methyl-6-(l,3-thiazol-5-yl)pyridine. 1H NMR (600 MHz, CDC13) delta 8.80 (s, 1H), 8.29 (s, 1H), 7.38 (s, 1H), 7.19 (s, 1H), 2.34 (s, 3H).

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, 73112-16-0, 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, Adding some certain compound to certain chemical reactions, such as: 73112-16-0, name is 2,6-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 73112-16-0.

[00170] A solution of n-BuLi (4.4 mL, 2.5 M in n-hexane, 11 mmol) was slowly added to a solution of 2,6-dibromo-4-methylpyridine (2.75 g, 10.9 mmol) in DCM (83 mL) at -78C under N2. After stirring for 1.5 hat -78 C, methyl 3- oxocyclopentanecarboxylate (1.54 g, 11.0 mmol) was added. The cooling bath was removed and the reaction mixture was stirred for 2 h, and then was quenched by addition of saturated aqueous NH4C1 solution. The reaction mixture was extracted with ethyl acetate, and the organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (isocratic elution, 8% ethyl acetate-petroleum ether) to give two product diastereomers. Peak 1(550 mg, yellow solid) was determined to be the 1R,3S and 1S,3R isomers, and peak 2 (350 mg, yellow oil) was determined to be the 1R,3R and 1S,3S isomers. MS (ES+) C13H16BrNO3 requires: 313, found: 314 [M+H].

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); 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

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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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. Safety of 2,6-Dibromo-4-methylpyridine

Step 1: Synthesis of (lS,4S)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexane- carboxylate and (lR,4R)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexane- carboxylate. (0253) (0254) (less polar by TLC) (more polar by TLC) (0255) A solution of 2,6-dibromo-4-methylpyridine (1.00 g, 3.98 mmol) in DCM (30 mL) was cooled to -78 C, and n-BuLi (2.5 M, 1.74 mL, 4.37 mmol) was added dropwise to the above solution at -78 C. The solution was stirred at -78 C for 15 minutes, followed by addition of ethyl 4-oxocyclohexanecarboxylate (811 mg, 4.77 mmol), and the resultant mixture was stirred at -78 C for 30 min. The mixture was then quenched by addition of saturated aqueous NH4C1 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 (lR,4R)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexanecarboxylate (less polar by TLC, 500 mg, 36.7%) as a white solid, MS (ES+) Ci5H2oBrN03 requires: 341, found: 342 [M+H]+, and (lS,4S)-ethyl 4-(6-bromo-4-methylpyridin-2-yl)-4-hydroxycyclohexanecarboxylate (more polar by TLC, 500 mg, 36.7%) as a white solid. MS (ES+) Ci5H20BrNO3 requires: 341, found: 342 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 73112-16-0.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; KIM, Joseph, L.; WILSON, Kevin, J.; WILSON, Douglas; DIPIETRO, Lucian, V.; (84 pag.)WO2017/79140; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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.

2,6-Dibromo-4-methylpyridine (3.76 g, 14.98 mmol) in dichloromethane (DCM) (80 mL) was added.Cool to -78 C. under nitrogen.While maintaining the internal temperature below -70 C,n-Butyllithium (2.5 M in hexane) (6.59 mL, 16.48 mmol) was added dropwise.After the addition is completeThe solution becomes a suspensionStir at -78 C. for 15 minutes.While keeping the internal temperature below -60 C,A solution of dihydrofuran-3 (2H) -one (1.548 g, 17.98 mmol) in 2 mL of DCM was added over 3 minutes.After the addition is completeReduce the temperature back to -78 C,Stir for 30 minutes.The product with saturated aqueous NH4Cl,Extracted with DCM.The organic portion was dried over MgSO 4, filtered and concentrated to give a residue that was purified on a silica gel column eluted with 0-50% ethyl acetate / heptane to give the product (2.13 g, yield). 55%).

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference 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.

To a vial were added 2,6-dibromo-4-methylpyridine (121 mg, 0.482 mmol), cw-butyl 4- [l-hydroxy-l-(l,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate (75 mg, 0.241 mmol), potassium carbonate (100 mg, 0.722 mmol), pivalic acid (5.59 mu, 0.048 mmol),tetrakis(triphenylphosphine)palladium(0) (11.1 mg, 9.63 mu?iotaomicronGamma) and N,N-dimethylacetamide (760 mu). The vial was sealed and placed under argon through 3 cycles of evacuation and argon flushing then reacted at 80 C overnight. The resulting mixture was cooled, diluted with ethyl acetate, filtered through a plug of CELITE and concentrated. The residue was purified by column chromatography on silica gel (0-100% ethyl acetate/hexanes) to afford racemic-cw-butyl 4- { 1 -[5-(6-bromo-4-methylpyridin-2-yl)- 1 ,3 -thiazol-2-yl]- 1 -hydroxyethyl } – cyclohexanecarboxylate.Two enantiomers were separated by chiral super critical fluid chromatography (ChiralTechnology IC-H, 2.1 x 25 cm, 5 uM, 70/30 ethanol/C02, Flow Rate: 70 mL/min, 8 min run time, WL: 220 nm). Elution was observed at 5.20 min and 6.08 min. Pooled fractions of each peak were concentrated under reduced pressure.Enantiomer 1 (retention time 5.20 min): MS ESI calc’d. for C22H29BrF3N203S [M + H+] 481 and 483, found 481 and 483.Enantiomer 2 (retention time 6.08 min): MS ESI calc’d. for C22H29BrF3N203S [M + H+] 481 and 483, found 481 and 483.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73112-16-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; DI FRANCESCO, Maria Emilia; HAIDLE, Andrew, M.; OTTE, Ryan, D.; ELLIS, John Michael; CHILDERS, Kaleen Konrad; NORTHRUP, Alan, B.; YANG, Liping; WO2012/154520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 73112-16-0 , The common heterocyclic compound, 73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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.

1A Preparation of 2-bromo-4-methyl-6-(3-trifluoromethyl-1H-pyrazol-1-yl)-pyridine A mixture of 2,6-dibromo-4-methylpyridine (33 mmol, obtained according to the method disclosed by WO 94/22833), 3-trifluoromethyl-1H-pyrazole (21 mmol), potassium carbonate (45 mmol) and N,N-dimethylformamide ((50 mL) is heated at 90 C. for 4 hours. The reaction mixture is partitioned between ethyl acetate ands water. The separated organic phase is washed with brine, dried over sodium sulfate and evaporated in vacuo to provide an oily residue which is purified by flash chromatography. To yield 1.9 g of the title compound.

The synthetic route of 73112-16-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; US6448204; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, 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.73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

A dry round bottomed flask was charged with 2-aniino-4-cyclopropylpyridine (5.00 g, 31.7 mmol) and 2,6-dibromo-4-methylpyridine (7.95 g, 31.7 mmol). The reaction vessel was placed under an atmosphere of nitrogen (3x vacuum/N2 cycle), then 1,4-dioxane (lOOmL) was added and the mixture was degassed with a steady stream of nitrogen for 30 minutes. Sodium tert- butoxide (3.35 g, 34.8 mmol) and l,r-6/s(di-te^butylphospMno)ferrocene palladium dichlonde (0.49 g, 0.75 mmol) were added to the reaction flask, then the reaction was stirred at room temperature for 15 minutes then heated to 50 C for five hours. After cooling to room temperature for 14 hours, the resulting reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were further washed with water and brine (200 mL portions). The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield an oil. The crude product was purified by silica gel chromatography (0-30% ethyl acetate/hexanes) to give the title compound as a brown solid. lH NMR (600 MHz, DMSO-d6) delta 9.80 (s, IH), 8.06 (d, J= 5.3 Hz, IH), 7.70 (s, IH), 7.23 (s,IH), 6.92 (s, IH), 6.61 (dd, J= 1.4, 5.3 Hz, IH), 2.25 (s, 3H), 1.91 – 1.78 (m, IH), 1.09 – 0.98 (m, 2H), 0.82 – 0.66 (m, 2H).

Statistics shows that 73112-16-0 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; DI FRANCESCO, Maria Emilia; HAIDLE, Andrew, M.; OTTE, Ryan, D.; ELLIS, John Michael; CHILDERS, Kaleen Konrad; NORTHRUP, Alan, B.; YANG, Liping; WO2012/154520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, 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 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 2,6-dibromo-4-methylpyridine (300 mg, 1.20 mmol), tert-butyl carbamate (168 mg, 1.44 mmol), sodium ie/t-butoxide (138 mg, 1.44 mmol) and l,l’-bis(di-tert- butylphosphino)ferrocene palladium dichloride (39.0 mg, 0.06 mmol) were dissolved in nitrogen sparged 2-MeTHF. The system was evacuated and purged with nitrogen (3X) then placed into 70C oil bath. After 3 hours, the temperature was increased to 80C for 4 hours. The reaction mixture was diluted with EtOAc and brine. The product was extracted with EtOAc, washed with brine, dried and concentrated under reduced pressure to afford crude iert-butyl {4-methyl-6- [(trimethylsilyl)ethynyl]pyridin-2-yl} carbamate. Copper (I) iodide (0.13 g, 0.7 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.24 g, 0.35 mmol) were added to the crude product and then dissolved in nitrogen sparged dimethylacetamide. The system was evacuated and purged with nitrogen (3X). Triethylamine (1.5 mL, 10.45 mmol) and trimethylsilylactylene (1.5 mL, 10.45 mmol) were added and the solution was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (25 mL) and brine. The product was extracted with EtOAc (25 mL), washed with brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5% EtOAc). The fractions were concentrated under reduced pressure, suspended in hexanes, filtered in vacuo and dried to afford iert-butyl {4-methyl-6-[(trimethylsilyl)ethynyl]pyridin-2-yl} carbamate. MS ESI calcd. for Ci6H25N202Si [M + H]+ 305, found 305.

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 73112-16-0, 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michelle R.; ROMEO, Eric T.; KATTAR, Solomon D.; CHRISTOPHER, Matthew; ALTMAN, Michael D.; NORTHRUP, Alan B.; ELLIS, John Michael; BOYLE, Brendan O’; DONOFRIO, Anthony; GRIMM, Jonathan; REUTERSHAN, Michael H.; CHILDERS, Kaleen Konrad; OTTE, Ryan D.; CASH, Brandon; DUCHARME, Yves; HAIDLE, Andrew M.; SPENCER, Kerrie; VITHARANA, Dilrukshi; WU, Lingyun; ZHANG, Li; ZHANG, Peng; BEAULIEU, Christian; GUAY, Daniel; WO2014/48065; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, 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.73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

A dry round bottomed flask was charged with 2-aniino-4-cyclopropylpyridine (5.00 g, 31.7 mmol) and 2,6-dibromo-4-methylpyridine (7.95 g, 31.7 mmol). The reaction vessel was placed under an atmosphere of nitrogen (3x vacuum/N2 cycle), then 1,4-dioxane (lOOmL) was added and the mixture was degassed with a steady stream of nitrogen for 30 minutes. Sodium tert- butoxide (3.35 g, 34.8 mmol) and l,r-6/s(di-te^butylphospMno)ferrocene palladium dichlonde (0.49 g, 0.75 mmol) were added to the reaction flask, then the reaction was stirred at room temperature for 15 minutes then heated to 50 C for five hours. After cooling to room temperature for 14 hours, the resulting reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were further washed with water and brine (200 mL portions). The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield an oil. The crude product was purified by silica gel chromatography (0-30% ethyl acetate/hexanes) to give the title compound as a brown solid. lH NMR (600 MHz, DMSO-d6) delta 9.80 (s, IH), 8.06 (d, J= 5.3 Hz, IH), 7.70 (s, IH), 7.23 (s,IH), 6.92 (s, IH), 6.61 (dd, J= 1.4, 5.3 Hz, IH), 2.25 (s, 3H), 1.91 – 1.78 (m, IH), 1.09 – 0.98 (m, 2H), 0.82 – 0.66 (m, 2H).

Statistics shows that 73112-16-0 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; DI FRANCESCO, Maria Emilia; HAIDLE, Andrew, M.; OTTE, Ryan, D.; ELLIS, John Michael; CHILDERS, Kaleen Konrad; NORTHRUP, Alan, B.; YANG, Liping; WO2012/154520; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem