Category: 22282-99-1

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. 22282-99-1, name is 4-Bromo-2-methylpyridine. A new synthetic method of this compound is introduced below., SDS of cas: 22282-99-1

Intermediate 331 -(4-Bromo-pyridin-2-yl)-cvclopropanecarboxylic acid ethyl esterStep 1 : (4-bromo-pyridin-2-yl)-acetic acid ethyl ester; Lithium diisopropylamide (2 mol/L in tetrahydrofuran/heptane/ethylbenzene, 3.00 mL) was added to a solution of 4-bromo-2-methylpyridine (2.00 g) and diethyl carbonate (1 .8 mL) in tetrahydrofuran (30 mL) cooled to -70 ‘C. The solution was stirred for 1 h prior to the addition of another portion of lithium diisopropylamide (2 mol/L in tetrahydrofuran/heptane/ ethylbenzene, 3.00 mL). Stirring was continued at -70 C for one more hour and then the reaction was quenched by the addition of water. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (Na2S04). The solvent was evaporated and the residue was chromatographed on silica gel(cyclohexane/ethyl acetate 95:5?1 :1 ) to give the title compound. Yield: 2.35 g (83% of theory); LC (method 3): tR = 2.86 min; Mass spectrum (ESI+): m/z = 244/246 (Br) [M+H]+.

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, 22282-99-1, 4-Bromo-2-methylpyridine.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LEFTHERIS, Katerina; ZHUANG, Linghang; TICE, Colin, M.; SINGH, Suresh, B.; YE, Yuanjie; XU, Zhenrong; HIMMELSBACH, Frank; ECKHARDT, Matthias; WO2011/159760; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-99-1 , The common heterocyclic compound, 22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, 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 4-bromo-2-methyl-pyridine (2.00 g, 11.6 mmol, CAS 22282-99- 1) and diethyl carbonate (1.65 g, 13.9 mmol, 1.68 mL) in THF (15.0 mL) was added LDA (2 M, 11.63 mL) at -60 C dropwise. Then the mixture was stirred at -60 C for 2 hours. On completion, the reaction mixture was quenched by addition of saturated ammonium chloride solution 30 mL at 0 C, and extracted with ethyl acetate 60 mL (3 X 20 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 20:1 to 8:1) to give the title compound (1.30 g, 46% yield) as a yellow oil.1H NMR (400MHz, CDCl3) delta = 8.40 (d, J = 5.2 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.40 (dd, J = 1.6, 5.2 Hz, 1H), 4.21 (q, J = 7.2 Hz, 2H), 3.83 (s, 2H), 1.29 (t, J = 7.2 Hz, 3H).

The synthetic route of 22282-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-99-1 , The common heterocyclic compound, 22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, 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 4-bromo-2-methyl-pyridine (2.00 g, 11.6 mmol, CAS 22282-99- 1) and diethyl carbonate (1.65 g, 13.9 mmol, 1.68 mL) in THF (15.0 mL) was added LDA (2 M, 11.63 mL) at -60 C dropwise. Then the mixture was stirred at -60 C for 2 hours. On completion, the reaction mixture was quenched by addition of saturated ammonium chloride solution 30 mL at 0 C, and extracted with ethyl acetate 60 mL (3 X 20 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 20:1 to 8:1) to give the title compound (1.30 g, 46% yield) as a yellow oil.1H NMR (400MHz, CDCl3) delta = 8.40 (d, J = 5.2 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.40 (dd, J = 1.6, 5.2 Hz, 1H), 4.21 (q, J = 7.2 Hz, 2H), 3.83 (s, 2H), 1.29 (t, J = 7.2 Hz, 3H).

The synthetic route of 22282-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22282-99-1, 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.22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, molecular weight is 172.02, as common compound, the synthetic route is as follows.

To a solution of compound 5-5 (26 g, 151.14 mmol, 1 eq) and compound 5-6 (23.40 g, 198.09 mmol, 24 mL, 1.31 eq) in tetrahydrofuran (300 mL) was added LDA (2 M, 39 mL) at -70C under nitrogen atmosphere. The mixture was stirred at -70C for 1 hour prior to the addition of LDA (2 M, 39.00 mL). The reaction was stirred at -70C for another 1 hour. LCMS showed 25% of starting material remained and 54% of desired compound mass was detected. The reaction mixture was quenched with water (50 mL), and extracted with ethyl acetate (100 mLx3). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by reverse phase flash (trifluoroacetic acid condition). Then basified with saturated sodium bicarbonate (10 mL), extracted with ethyl acetate (100 mLx3). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to give compound 5-7 (22 g, 59.63% yield) as yellow oil. 1H NMR (CDCl3, 400 MHz): d 8.45 (d, J = 5.6 Hz, 1H), 7.61 (d, J = 2.0 Hz, 1H), 7.50 (dd, J1 =5.6 Hz, J2 = 2.0 Hz, 1H), 4.20 (q, J = 7.2 Hz, 2H), 3.89 (s, 2H), 1.27 (t, J = 7.2 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 22282-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-99-1, 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 22282-99-1, name is 4-Bromo-2-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-Bromo-2-methylpyridine (70 g, 407 mmol) and triethylamine (141 mL, 1.02 mol) were combined in DMF (400 mL) and MeOH (400 mL). The solution was purged with N2 for 10 minutes, and then Pd(dppf)2 (15 g, 20.35 mmol) was added. Carbon monoxide was bubbled through the mixture for 10 minutes, and then the reaction was stirred at 75 C overnight. The mixture was concentrated and the residue was diluted with 1 : 1 EtOAc:hexanes (2L) and washed 10 times with H20/brine. The aqueous layer was back-extracted 6 times, and the combined organic layers were dried, filtered, and concentrated. The residue was purified by silica gel chromatography to give the title compound.

According to the analysis of related databases, 22282-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; STEARNS, Brian, Andrew; ROPPE, Jeffrey, Roger; PARR, Timothy, Andrew; STOCK, Nicholas, Simon; VOLKOTS, Deborah; HUTCHINSON, John, Howard; WO2011/38086; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22282-99-1, 4-Bromo-2-methylpyridine, 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, 22282-99-1, blongs to pyridine-derivatives compound. Product Details of 22282-99-1

[0566] Step 1: ethyl 2-(4-bromopyridin-2-yl)acetate – To a stirred solution of 4-bromo-2-methylpyridine (1.2 g, 4.93 mmol, 1.0 eq) in THF (15 mL), was added diethyl carbonate (0.698 mL, 5.92 mmol, 1.2 eq) and the mixture stirred at -78C under nitrogen atmosphere. LDA(2′-78C for 2h. The reaction was then quenched with saturated sodium chloride solution and the product extracted with EtOAc (2′-(4-bromopyridin-2-yl)acetate (0.500 g, 30%) as a pale yellow liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-99-1, its application will become more common.

Reference:
Patent; CAPULUS THERAPEUTICS, LLC; GREEN, Michael John; HART, Barry Patrick; (341 pag.)WO2019/148125; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 22282-99-1, 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.22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, molecular weight is 172.02, as common compound, the synthetic route is as follows.

To a stirred solution of 4-bromo-2- methylpyridine (3 g, 17.44 mmol) and diethyl carbonate (2.75 ml, 22.67 mmol) in THF (30 ml)was added LDA (4mL) (2M in THF/hept/ethylbenzene) at -78C. The solution was stirred for 1 h prior to the addition of another portion of LDA (4.00 mL). Stirring was continued at -70C for one more hour and then the reaction was quenched by the addition of water. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (Na2504). The solvent was evaporated and the residue was purified byflash columnchromatography on silica gel (0-100% EtOAc in Hex) to give the title compound. LC/MS =245.75 [M+lj

The chemical industry reduces the impact on the environment during synthesis 22282-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; XU, Jiayi; ZHOU, Wei; (123 pag.)WO2017/74833; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem