Category: 175205-82-0

Shoberu, Adedamola et al. published their research in Organic Chemistry Frontiers in 2021 | CAS: 175205-82-0

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 175205-82-0

Copper-catalyzed, N-auxiliary group-controlled switchable transannulation/nitration initiated by nitro radicals: selective synthesis of pyridoquinazolones and 3-nitroindoles was written by Shoberu, Adedamola;Li, Cheng-Kun;Qian, Hai-Feng;Zou, Jian-Ping. And the article was included in Organic Chemistry Frontiers in 2021.Reference of 175205-82-0 This article mentions the following:

Herein, a strategy based on the judicious choice of N-auxiliaries, which stabilize the substrates as well as allow precise and predictable control over their reactivity with tert-Bu nitrite was described. Thus, the stage was set for the copper-assisted, controllable synthesis of pyridoquinazolones or 3-nitroindoles. Mechanistic studies implicate a switch in the mechanism, in which N-2-pyridylindoles reacted via a nitrosation/transannulation process and N-2-pyridoylindoles underwent an amide bond dissociation/nitration sequence. Notably, the subsequent removal of the auxiliary groups was not required in these reactions. In the experiment, the researchers used many compounds, for example, 2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0Reference of 175205-82-0).

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 175205-82-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Shoberu, Adedamola et al. published their research in Organic Chemistry Frontiers in 2021 | CAS: 175205-82-0

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 175205-82-0

Copper-catalyzed, N-auxiliary group-controlled switchable transannulation/nitration initiated by nitro radicals: selective synthesis of pyridoquinazolones and 3-nitroindoles was written by Shoberu, Adedamola;Li, Cheng-Kun;Qian, Hai-Feng;Zou, Jian-Ping. And the article was included in Organic Chemistry Frontiers in 2021.Reference of 175205-82-0 This article mentions the following:

Herein, a strategy based on the judicious choice of N-auxiliaries, which stabilize the substrates as well as allow precise and predictable control over their reactivity with tert-Bu nitrite was described. Thus, the stage was set for the copper-assisted, controllable synthesis of pyridoquinazolones or 3-nitroindoles. Mechanistic studies implicate a switch in the mechanism, in which N-2-pyridylindoles reacted via a nitrosation/transannulation process and N-2-pyridoylindoles underwent an amide bond dissociation/nitration sequence. Notably, the subsequent removal of the auxiliary groups was not required in these reactions. In the experiment, the researchers used many compounds, for example, 2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0Reference of 175205-82-0).

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 175205-82-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The origin of a common compound about 2-Bromo-3-(trifluoromethyl)pyridine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175205-82-0, its application will become more common.

Application of 175205-82-0, 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 175205-82-0 as follows.

2-Bromo-3-(trifluoromethyl)pyridine (1 .5 g, 6.63 mmol) is added to a solution of example 16a (500 mg, 2.21 mmol) in TEA (3.5 mL, 25.25 mmol) and dry ACN (14 mL) at rt. Then Copper (I) Iodide (84 mg, 0.442 mmol) and dichlorobis(triphenylphosphine)palladium(II) (155 mg, 0.221 mmol) are added and stirring is continued overnight. Solvent is evaporated under reduced pressure and the crude is purified byflash chromatography (eluent 0-40% EtOAc/cyclohexane) to furnish the title compound (800 mg, 99%).U PLC-MS (Method 2): R = 1 .23 mm MS (ESI pos): mlz = 363 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175205-82-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new synthetic route of 2-Bromo-3-(trifluoromethyl)pyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, 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: 175205-82-0, blongs to pyridine-derivatives compound. SDS of cas: 175205-82-0

Step 2. Synthesis of methyl 3-amino-6-(3-(trifluoromethyl)pyridin-2-yl)pyrazine-2- carboxylate In a 500 mL round-bottom flask equipped with a magnetic stirrer and argon inlet, methyl 3-amino-6-(trimethylstannyl)pyrazine-2-carboxylate (20.92 g, 55.0 mmol), 2-Bromo-3- (trifluoromethyl) pyridine (14.38 g, 60.5 mmol), Pd2(dba)3 (5.54 g, 6.05 mmol) and P(o-Tol)3 (3.79 g, 12.09 mmol) were dissolved in DMF (100 ml) at rt, followed by addition of NEt3 (10.72 ml, 77 mmol). The reaction mixture was heated to 110C under argon for 1 h. After cooling to rt, the reaction mixture was filtered through celite, washed with ethyl acetate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using ethyl acetate heptane which gave methyl 3-amino-6-(3-(trifluoromethyl)pyridin-2-yl)pyrazine-2- carboxylate (7.8 g) as a yellow solid. LC-MS (Basic Method ): ret.time= 0.93 min, M+H = 299.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LUZZIO, Michael Joseph; PAPILLON, Julien; VISSER, Michael Scott; (213 pag.)WO2016/20864; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Brief introduction of 2-Bromo-3-(trifluoromethyl)pyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Electric Literature of 175205-82-0, 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. 175205-82-0, name is 2-Bromo-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Step 2: A mixture of 2-bromo-3-(trifluoromethyl)pyridine (50 mg), 2-[4- (ethylsulfonyl)phenyl]-N-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yI)phenyl]acetamide (104 mg), Cs2C03 (87 mg) and PdCl2(dppf)-CH2Cl2 adduct (10 mg) in acetonitrile (1.5 mL) and water (0.5 mL) was sealed in a vessel and heated in the microwave at 100C for 30 mins. The reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by MDAP to afford 2-[4-(ethylsulfonyl)phenyl]-N-{4-[3-(trifluoromethyl)-2- pyridinyl]phenyl}acetamide (32 mg) as a white solid. ‘H-NMR (400 MHz, DMSO-rf6) delta ppm 1.10 (t, J= 7.2 Hz, 3H), 3.28 (q, J= 7.2 Hz, 2H), 3.85 (s, 2H), 7.42 (d, J= 8.4 Hz, 2H), 7.62 (m, 3H), 7.70 (d, J= 8.4 Hz, 2H), 7.86 (d, J= 8.4 Hz, 2H), 8.28 (dd, = 1.2 Hz, 8.0 Hz, 1H), 8.89 (d, J= 4.4 Hz, 1H), 10.46 (s, 1H); 19F-NMR (376 MHz, DMSO-t?) delta ppm -55.98; MS(ES+) m/z 449 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175205-82-0, 2-Bromo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem