Category: 185017-72-5

Adding a certain compound to certain chemical reactions, such as: 185017-72-5, 3-Bromo-2-chloro-6-picoline, 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, 185017-72-5, blongs to pyridine-derivatives compound. Computed Properties of C6H5BrClN

a) l-(2-Chloro-6-methylpyridin-3-yl)cyclobutanol A suspension of molecular sieves (4 A) and 3-bromo-2-chloro-6-methylpyridine (CAN 185017-72-5, 5 g, 24.2 mmol) in THF (50 mL) was cooled to -15 C. 1.3 M isopropyl magnesium chloride lithium chloride complex solution in THF (19.6 mL, 25.4 mmol) was added within 30 min. Stirring was continued for 1 h at -15 C. Cyclobutanone (1.87 g, 2.00 mL, 26.6 mmol) was slowly added. Stirring was continued for 2 h at -15 C and for further 2 h at 0 C. Water (2.5 mL) was added, the mixture was concentrated in vacuo, and poured onto sat. aqueous NH4C1 solution. The mixture was extracted with EtOAc (2 x 100 mL). The combined extracts were washed with ice water (50 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 140 g, heptane / EtOAc 0-40% in 120 min.) to give the title compound (3.33 g, 70%) as white solid, MS (ESI): m/e = 198.1 [MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,185017-72-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BENDELS, Stefanie; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHAFFTER, Ernst; SCHULZ-GASCH, Tanja; WO2014/86806; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 185017-72-5, 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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, 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.

To a solution of 3-bromo-2-chloro-6-methylpyridine (60 mg, 0.291 mmol) in DMA (2 mL) was added 2- (cyclopentyldifluoromethyl) oxazole (50 mg, 0.267 mmol) , KOAc (55 mg, 0.560 mmol) and Pd (PPh3)4(30 mg, 0.026 mmol) under N2atmosphere and the mixture was stirred at 80 overnight. Then the mixture was cooled to rt, filtered and the filtrate was concentrated in vacuum, the residue was purified by prep. TLC (EA: PE5: 1) to give the title compound. MS: 313 (M+1) .

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 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-2-chloro-6-picoline

Example 633-[4-Chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-6-methyl-2-pyridinecarboxylic acidCla)2-Chloro-5-(2-chloro-6-methyl-3-pyridinyl)-JV-(tricyclo[3.3.1.13’7]dec-l-ylmethyl)-benzamideA mixture of [4-chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-boronic acid (Example 2 (a)) (174 mg), 3-bromo-2-chloro-6-methyl-pyridine (104 mg),potassium carbonate (138 mg) and Z?w(triphenylphosphine)palladium(II) chloride (27 mg)in tetrahydrofuran (2 mL) and water (2 mL) was stirred at room temperature under anitrogen atmosphere over 72 hours. The mixture was filtered through diatomaceous earth,washing with methanol, and the filtrate was concentrated in vacuo. Purification bychromatography (SiOa, zsohexane:emyl acetate 1:1 as eluant) gave the sub-title compoundas a solid (135 mg).MS: APCI(+ve) 429/431 (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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; ASTRAZENECA AB; WO2006/25783; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 185017-72-5, 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.185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.

To a vial containing 3-amino-S -(3,5 -dimethylisoxazol-4-yl)benzonitrile (80 mg,0.375 mmol) was added toluene (2 mL), 3-bromo-2-chloro-6-methylpyridine (85 mg,0.413 mmol), cesium carbonate (244 mg, 0.750 mmol) and chloro(2-dicyclohexylphosphino-2? ,4? ,6 ? -triisopropyl- 1,1? -biphenyl) [2-(2? -amino- 1,1? -biphenyl)jpalladium(II) (CAS1310584-14-5, 7.4 mg, 9.38 imol). The reaction mixture was degassed by bubbling argon through the reaction mixture. The vial was capped with a pressure safe septum screw-cap and heated at 100 C. After 5 h, the reaction mixture was cooled, diluted with dichloromethane, and filtered through celite. The filtrate was concentrated and purified by silica gel chromatography to give 3-((2-chloro-6-methylpyridin-3-yl)amino)-5 -(3,5 -dimethylisoxazol-4-yl)benzonitrile (29 mg, 23%):HPLC: RT=0.93 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.05%TFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z 339.1/340.9 35C1/37C1 [M+ljt

Statistics shows that 185017-72-5 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUESNELLE, Claude A.; HARIKRISHNAN, Lalgudi S.; HILL, Matthew D.; (180 pag.)WO2016/183114; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 185017-72-5, 3-Bromo-2-chloro-6-picoline, 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, name: 3-Bromo-2-chloro-6-picoline, blongs to pyridine-derivatives compound. name: 3-Bromo-2-chloro-6-picoline

To a vial containing 3-(3,5-dimethylisoxazol-4-yl)aniline (96 mg, 0.5 10 mmol)was added 3-bromo-2-chloro-6-methylpyridine (211 mg, 1.02 mmol), cesium carbonate(332 mg, 1.02 mmol), chloro(2-dicyclohexylphosphino-2 ? ,4 ? ,6? -triisopropyl- 1,1? – biphenyl)[2-(2? -amino-i, 1? -biphenyl)jpalladium(II) (CAS 1310584-14-5, 10.0 mg, 0.013 mmol), and toluene (2 mL). The resulting suspension was degassed by bubbling argon through the reaction mixture. The vial was capped with a pressure-safe septum cap andheated to 100 C for 3 h. The reaction mixture was cooled to room temperature and filtered through a pad of silica gel. The filter pad was washed with ethyl acetate. The filtrate was concentrated and purified by silica gel chromatography with 0 – 100% ethyl acetate in hexanes. The product containing fractions were evaporated to give 2-chloro-N- (3 -(3 ,5-dimethylisoxazol-4-yl)phenyl)-6-methylpyridin-3 -amine (49 mg, 31%) as a palebrown solid: HPLC: RT=0.97 mm (Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0.05%TFA, 1 mm gradient, wavelength=254nrn); MS (ES): m/z= 314.2/3 15.9 35C1/37C1 [M+ljt

At the same time, in my other blogs, there are other synthetic methods of this type of compound,185017-72-5, 3-Bromo-2-chloro-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUESNELLE, Claude A.; HARIKRISHNAN, Lalgudi S.; HILL, Matthew D.; (180 pag.)WO2016/183114; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Bromo-2-chloro-6-picoline

General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-chloropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Article; Anchan, Kavitha; Baburajan, Poongavanam; Puttappa, Nagaswarupa H.; Kumar Sarkar, Sujit; Synthetic Communications; vol. 50; 3; (2020); p. 348 – 360;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Bromo-2-chloro-6-picoline

General procedure: Method A: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-fluoropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DMAP (2.5 mmol). The tube was purged with argon. Then DMF (10V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a preheated oil bath at 120 0C for 8 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone. Method B: A sealed tube equipped with a magnetic stir bar was charged with the corresponding 3-bromo-2-chloropyridine (1 mmol), amino phenol (1 mmol), Pd(OAc)2 (5 mol%), xantphos (5 mol%) and DBU (2.5 mmol). The tube was purged with argon. Then DMF (10 V) was added followed by the addition of Co2(CO)8 (0.25 mmol). The tube was closed with seal plug instantly. The reaction tube was placed in a pre heated oil bath at 135 0C for 12 h. On completion, the reaction mixture was cooled to room temperature, added water and ethyl acetate (1:1). Precipitated solid was filtered through a Celite bed. The bed was washed thoroughly with ethyl acetate. Organic layer was separated. Aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure and purified by flash column chromatography on silica gel (230-400 mesh) with ethyl acetate and petroleum ether as eluent to afford the corresponding pyridobenzoxazepinone.

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, 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Article; Anchan, Kavitha; Baburajan, Poongavanam; Puttappa, Nagaswarupa H.; Kumar Sarkar, Sujit; Synthetic Communications; vol. 50; 3; (2020); p. 348 – 360;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185017-72-5, 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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows.

(5-Bromo-6-methoxy-pyridin-2-yl)-methanol (356a) step a-To a solution of 3-bromo-2-chloro-6-methyl-pyridine (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50 C. overnight. The resulted solution was cooled and partitioned between DCM and sat’d. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluding with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of 3-bromo-2-chloro-6-methyl-pyridine 1-oxide (357a) as a white solid. step b-A solution of 357a (0.5 g) and 0.5 M NaOMe/MeOH (4.9 mL) was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the residue loaded on a SiO2 column and eluted with 5% MeOH/DCM to afford 3-bromo-2-methoxy-6-methyl-pyridine 1-oxide (357b).

According to the analysis of related databases, 185017-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2010/21423; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185017-72-5, 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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows.

(5-Bromo-6-methoxy-pyridin-2-yl)-methanol (356a) step a-To a solution of 3-bromo-2-chloro-6-methyl-pyridine (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50 C. overnight. The resulted solution was cooled and partitioned between DCM and sat’d. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluding with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of 3-bromo-2-chloro-6-methyl-pyridine 1-oxide (357a) as a white solid. step b-A solution of 357a (0.5 g) and 0.5 M NaOMe/MeOH (4.9 mL) was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the residue loaded on a SiO2 column and eluted with 5% MeOH/DCM to afford 3-bromo-2-methoxy-6-methyl-pyridine 1-oxide (357b).

According to the analysis of related databases, 185017-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2010/21423; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 185017-72-5, 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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-2-chloro-6-methylpyridine (47.8 mg, 0.231 mmol) and 2- (cyclopentylmethyl) oxazole (35 mg, 0.231 mmol) in DMA (1 mL) was added potassium acetate (45.4 mg, 0.463 mmol) and Pd (PPh3)4(26.7 mg, 0.023 mmol) under N2. The reaction mixture was stirred at 90 overnight. The reaction mixture was cooled to room temperature, filtered and the filtration was concentrated in vacuum, the residue was purified by Prep. TLC (PE: EA 10: 1) to give the title compound. MS: 277.1 (M+1) .1H NMR (CDCl3-d, 400 MHz) : delta 7.95 (d, J 7.8 Hz, 1H) , 7.66 (bs, 1H) , 7.16 (d, J 7.8 Hz, 1H) , 2.82 (d, J 7.0 Hz, 2H) , 2.31-2.39 (m, 1H) , 1.83 (bs, 4H) , 1.65 (bs, 2H) , 1.27 (d, J 5.5 Hz, 2H) .

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 185017-72-5, 3-Bromo-2-chloro-6-picoline.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem