1231930-13-4 | Pyridine-derivatives

Extracurricular laboratory: Synthetic route of 3-Bromo-2-methyl-6-nitropyridine

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 1231930-13-4, 3-Bromo-2-methyl-6-nitropyridine.

Reference of 1231930-13-4, 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. 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine, molecular formula is C6H5BrN2O2, 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 solution of Example A6 (1.7 g, 6.40 mmol) in dioxane (30 mL) was sparged with Ar, treated with acetamide (1.512 g, 25.6 mmol), Cs2CO3 (2.085 g, 6.40 mmol), X-Phos (0.153 g, 0.320 mmol) and Pd2(dba)3 (0.293 g, 0.320 mmol) and heated at 80 C. for 20 h. The mixture was cooled to RT, treated with EtOAc, the solids removed via filtration through diatomaceous earth and rinsed well with EtOAc. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/DCM) to afford N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (450 mg, 24%) as a light yellow solid. MS (ESI) m/z: 289.1 (M+H+).

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

Extracurricular laboratory: Synthetic route of 3-Bromo-2-methyl-6-nitropyridine

Some scientific research about 1231930-13-4

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

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.

Some scientific research about 1231930-13-4

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

The origin of a common compound about 1231930-13-4

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1231930-13-4, 3-Bromo-2-methyl-6-nitropyridine, and friends who are interested can also refer to it.

Related Products of 1231930-13-4, 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. 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine. A new synthetic method of this compound is introduced below.

2-(4-methyl-1H-imidazol-1-yl)pyridin-4-ol (200 mg, 1.14 mmol) was dissolved in N,N-dimethylformamide (5 mL), and then 3-bromo-2-methyl-6-nitropyridine (250 mg, 1.14 mmol), and potassium carbonate (472 g, 3.42 mmol) were added. The reaction solution was stirred at 90 C. for 16 hrs, then poured into water (200 mL), and then extracted twice with ethyl acetate (50 mL*2). The organic phases were combined and washed once with a brine (100 mL), dried over sodium sulfate, then concentrated, and separated by column chromatography (eluent: petroleum etherpetroleum ether/ethyl acetate (4:6)) to obtain 2-methyl-3-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)-6-nitropyridine (60 mg, yield 17%). MS m/z (ESI): 311 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1231930-13-4, 3-Bromo-2-methyl-6-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Abbisko Therapeutics Co., Ltd.; ZHAO, Baowei; ZHANG, Mingming; YU, Hongping; YANG, Shuqun; CHEN, Zhui; XU, Yaochang; US2020/71302; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Sources of common compounds: 3-Bromo-2-methyl-6-nitropyridine

According to the analysis of related databases, 1231930-13-4, the application of this compound in the production field has become more and more popular.

Synthetic Route of 1231930-13-4, Adding some certain compound to certain chemical reactions, such as: 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine,molecular formula is C6H5BrN2O2, 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 1231930-13-4.

A mixture of Example C6 (2 g, 5.15 mmol), Example A6 (1.053 g, 3.96 mmol) and Pd(PPh3)4 (0.229 g, 0.198 mmol) in toluene (20 mL), sparged with Ar and heated at 105 C. overnight. The mixture was cooled to RT, treated 10% KF (aq) and EtOAc and stirred at RT for 2 h. The solids were removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate was washed with satd. NaHCO3, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 2-methyl-5-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (1.06 g, 81%). 1H NMR (400 MHz, DMSO-d6): delta 8.50 (d, J=5.7 Hz, 1H), 8.34 (s, 1H), 8.24 (d, J=8.7 Hz, 1H), 7.88 (d, J=8.7 Hz, 1H), 7.72 (d, J=2.4 Hz, 1H), 7.02 (dd, J=5.7, 2.4 Hz, 1H), 2.65 (s, 3H), 2.50 (s, 3H); MS (ESI) m/z: 329.1 (M+H+).

According to the analysis of related databases, 1231930-13-4, the application of this compound in the production field has become more and more popular.

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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. 1231930-13-4, 3-Bromo-2-methyl-6-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference of 1231930-13-4 ,Some common heterocyclic compound, 1231930-13-4, 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.

3-bromo-2-methyl-6-nitropyridine (2.2 g, 10.1 mmol), bis(pinacolato)diboron 1.3.0 g, 12.1 mmol), Pd(dppf)Cl2 (200 mg), and potassium acetate (3.0 g, 30.4 mmol) were dissolved in 1,4-dioxane (40 mL). The reaction solution was stirred at 110 C. for 2 hrs under nitrogen protection. When the LCMS showed that the reaction completed, the reaction solution was filtered through celite, and the filtrate is concentrated to dryness. The residue was separated by a rapid silica gel column (020% EA:PE) to obtain 2-methyl-6-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.8 g, yield 67%), which was directly used in the next reaction.