Category: 73583-41-2

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.73583-41-2, name is 4-Bromo-3-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.441, as common compound, the synthetic route is as follows.Application In Synthesis of 4-Bromo-3-chloropyridine

Step 1: Preparation of 3-chloro-4-((trimethylsilyl)ethynyl)pyridine A mixture of 4-bromo-3-chloropyridine (2 g, 10.5 mmol), bis(triphenylphosphine)palladium(II) chloride (0.37 g, 0.52 mmol), copper iodide (0.2 g, 1.05 mmol) in triethylamine (20 mL) was degassed and re-filled with nitrogen (2*). Then ethynyltrimethylsilane (4.4 mL, 31.4 mmol) was added dropwise by a syringe. After the addition, the reaction mixture was stirred at 60 C. for 18 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL*2). The combined organic phases were washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (Biotage, 40 g silica, eluted with ethyl acetate in petroleum ether from 10% to 15%) to give 3-chloro-4-((trimethylsilyl)ethynyl)pyridine (1.47 g, 7.03 mmol, 67%) as a yellow oil. LCMS (ESI) m/z: 210.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73583-41-2, 4-Bromo-3-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73583-41-2, 4-Bromo-3-chloropyridine, 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, 73583-41-2, blongs to pyridine-derivatives compound. Recommanded Product: 4-Bromo-3-chloropyridine

Step c: To a solution of tert-butyl (i-(6-amino-5-mercaptopyrazin-2-yl)-4-methylpiperidin-4-yl)carbamate(44 mg, 0.130 mmol), 4-bromo-3-chloropyridine (31.2 mg, 0.162 mmol), XantPhos (7.5 mg, 0.013 mmol), and Pd2 (dba)3 (5.9 mg, 0.0065 mmol) in dioxane (2 mL) was added (at RT and under N2) DIPEA (68 IL, 0.389 mmol). The resulting solution was stirred in a microwave reactor for 1 h at 110 C. and for 1 h at 125 C. After cooling to RT, the reaction was diluted with EtOAc and it was filtered through a pad of Celite followed by EtOAc (5 mL) wash. The volatiles were removed under reduced pressure. The result-ing residue was dissolved in DCM (3 mE) and it was treated with TFA (500 IL). The resulting mixture was stirred for 10 mm at RT. The volatiles were removed under reduced pressure and the resulting residue was purified by HPLC (gradient elution 15-40% acetonitrile in water, 5 mM NH4OH modifier) to give 6-(4-amino-4-methylpiperidin-1 – yl)-3-((3-chloropyridin-4-yl)thio)pyrazin-2-amine (8.5 mg, 0.024 mmol). ?H NMR (400 MHz, METHANOL-d4) oe 8.30 (s, 1H), 8.06 (d, J=5.56 Hz, 1H), 7.52 (s, 1H), 6.58 (d, J=5.31 Hz, 1H), 3.76 (ddd, J=13.64, 7.07, 4.29 Hz, 2H), 3.44-3.59 (m, 2H), 1.45-1.64 (m, 4H), 1.09-1.23 (m, 3H). HRMS calcd for C,5H2QC1N65 (M+H) 351.1159. found 351.1159. IC50 is 0.076 tM.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-41-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; Chen, Zhuoliang; Dore, Michael; Fortanet, Jorge Garcia; Karki, Rajesh; Kato, Mitsunori; LaMarche, Matthew J.; Perez, Lawrence Blas; Williams, Sarah; Sendzik, Martin; (63 pag.)US2017/1975; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73583-41-2 ,Some common heterocyclic compound, 73583-41-2, molecular formula is C5H3BrClN, 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.

General procedure: Toluene/tert-butanol(6 mL, v/v, 5:1) was added to the mixture of 4-piperidone ketal(1.0 mmol, 1.0 equiv), aryl bromide 15af. (1.1 mmol, 1.1 equiv),sodium tert-butoxide (1.0 mmol, 1.0 equiv), palladium diacetate(0.05 mmol, 0.05 equiv), and X-Phos (0.05 mmol, 0.05 equiv), andthe mixture was stirred in a microwave reactor under argon for15 min at 160 C. After the reaction vials were cooled to roomtemperature and filtered over celite, they were rinsed well withethyl acetate. The filtrate was subsequently evaporated underreduced pressure to obtain the compounds 16a-f.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-41-2, its application will become more common.

Reference:
Article; Wang, Zhengyu; Shi, Xiaofan; Zhang, Huan; Yu, Liang; Cheng, Yanhua; Zhang, Hefeng; Zhang, Huibin; Zhou, Jinpei; Chen, Jing; Shen, Xu; Duan, Wenhu; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 128 – 152;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73583-41-2, 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 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 01-51 Preparation of 3-[(3-chloropyridin-4-yl)amino]-2-methylcyclohex-2-en-l-one (01-51): 3- amino-2-methylcyclohex-2-enone (500 mg, 4 mmol), 4-bromo-3-chloropyridine (950 mg, 5 mmol), palladium acetate (90 mg, 0.4 mmol), BINAP (197 mg, 0.8 mmol), cesium carbonate (2.6 g, 8 mmol) and toluene (10 mL) were combined in a sealed flask and heated at 100C, for 18 h. At rt, the mixture was filtered and the filtrate was diluted with EtOAc (30 mL), washed with brine (3 x 10 mL), dried with Na2S04. The crude was purified by HPLC to afford the title compound (140 mg, 15% yield, white microcrystal, mp = 135-138C). 1H NMR (D6-DMSO) delta 1.46 (s, 3H), 1.83-1.88 (m, 2H), 2.31 (t, J= 6.7 Hz, 2H), 2.53-2.57 (m, 2H), 6.84 (d, J= 6.1 Hz, 1H), 8.06 (s, 1H), 8.29 (d, J= 6.1 Hz, 1H), 8.48 (s, 1H). 13C NMR (D6-DMSO) delta 10.9, 20.6, 28.7, 36.7, 115.7, 117.1, 121.2, 144.7, 148.3, 148.3, 149.2, 154.4, 197.0. LCMS t = 1.9 min, m/z Calcd for Ci2Hi4ClN20; Ci2Hi3ClN2NaO 237.080; 259.061 [M+H]+; [2M+H]+, Found 237.080; 259.180.

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 73583-41-2, 4-Bromo-3-chloropyridine.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; ZHOU, Ming-Ming; OHLMEYER, Michael; VINCEK, Adam; ZAWARE, Nilesh; WO2015/31824; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73583-41-2, 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 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 01-51 Preparation of 3-[(3-chloropyridin-4-yl)amino]-2-methylcyclohex-2-en-l-one (01-51): 3- amino-2-methylcyclohex-2-enone (500 mg, 4 mmol), 4-bromo-3-chloropyridine (950 mg, 5 mmol), palladium acetate (90 mg, 0.4 mmol), BINAP (197 mg, 0.8 mmol), cesium carbonate (2.6 g, 8 mmol) and toluene (10 mL) were combined in a sealed flask and heated at 100C, for 18 h. At rt, the mixture was filtered and the filtrate was diluted with EtOAc (30 mL), washed with brine (3 x 10 mL), dried with Na2S04. The crude was purified by HPLC to afford the title compound (140 mg, 15% yield, white microcrystal, mp = 135-138C). 1H NMR (D6-DMSO) delta 1.46 (s, 3H), 1.83-1.88 (m, 2H), 2.31 (t, J= 6.7 Hz, 2H), 2.53-2.57 (m, 2H), 6.84 (d, J= 6.1 Hz, 1H), 8.06 (s, 1H), 8.29 (d, J= 6.1 Hz, 1H), 8.48 (s, 1H). 13C NMR (D6-DMSO) delta 10.9, 20.6, 28.7, 36.7, 115.7, 117.1, 121.2, 144.7, 148.3, 148.3, 149.2, 154.4, 197.0. LCMS t = 1.9 min, m/z Calcd for Ci2Hi4ClN20; Ci2Hi3ClN2NaO 237.080; 259.061 [M+H]+; [2M+H]+, Found 237.080; 259.180.

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 73583-41-2, 4-Bromo-3-chloropyridine.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; ZHOU, Ming-Ming; OHLMEYER, Michael; VINCEK, Adam; ZAWARE, Nilesh; WO2015/31824; (2015); 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. 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3BrClN

Step 2: N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane- 1 ,2-diamine [00252] A mixture of 4-bromo-3-chloropyridine (0.171 g, 0.886 mmol), N1-(2-aminoethyl)- N2-(7-chloroquinolin-4-yl)-N1-methylethane-l,2-diamine (0.247 g, 0.886 mmol), Pd(OAc)2 (22 mg), BINAP (0.12 g), and K3P04 (1.0 g) in 1,4-dioxane (8.9 mL) was degassed with argon for 5 min and then stirred at 100 C for 16.5 h in a sealed tube. The reaction mixture was cooled to room temperature, filtered through Celite, and concentrated in vacuo. Purification by silica gel chromatography using CH2Cl2/CH3OH/NH4OH (270:9: 1, and 180:9: 1) afforded N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane-l,2-diamine (0.276 g, 80%) as a pale-yellow oil, and further lyophilization with CH3CN/H20 gave an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 2.32 (s, 3H); 2.66 (t, J = 6.3, 2H); 2.72 (t, J = 6.6, 2H); 3.26 (q, J = 5.7, 2H); 3.40 (q, J = 6.0, 2H); 6.04 (t, J = 5.0, 1H); 6.50 (d, J = 5.4, 1H); 6.64 (d, J = 5.7, 1H); 7.24 (t, J = 4.8, 1H); 7.43 (dd, J = 2.1, 9.0, 1H); 7.78 (d, J = 2.1, 1H); 8.02 (d, J = 5.7, lH); 8.11 (s, 1H); 8.20 (d, J = 9.3, 1H); 8.38 (d, J = 5.4, 1H). Mass spectrum (ESI) m/e = 390.1 (M+l).

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, 73583-41-2, 4-Bromo-3-chloropyridine.

Reference:
Patent; PRESAGE BIOSCIENCES, INC.; DECKWERTH, Thomas; KLEINMAN, Edward; RUAN, Fuqiang; BAKER, William; KLINGHOFFER, Richard; (126 pag.)WO2016/196393; (2016); A2;,
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. 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3BrClN

Step 2: N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane- 1 ,2-diamine [00252] A mixture of 4-bromo-3-chloropyridine (0.171 g, 0.886 mmol), N1-(2-aminoethyl)- N2-(7-chloroquinolin-4-yl)-N1-methylethane-l,2-diamine (0.247 g, 0.886 mmol), Pd(OAc)2 (22 mg), BINAP (0.12 g), and K3P04 (1.0 g) in 1,4-dioxane (8.9 mL) was degassed with argon for 5 min and then stirred at 100 C for 16.5 h in a sealed tube. The reaction mixture was cooled to room temperature, filtered through Celite, and concentrated in vacuo. Purification by silica gel chromatography using CH2Cl2/CH3OH/NH4OH (270:9: 1, and 180:9: 1) afforded N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane-l,2-diamine (0.276 g, 80%) as a pale-yellow oil, and further lyophilization with CH3CN/H20 gave an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 2.32 (s, 3H); 2.66 (t, J = 6.3, 2H); 2.72 (t, J = 6.6, 2H); 3.26 (q, J = 5.7, 2H); 3.40 (q, J = 6.0, 2H); 6.04 (t, J = 5.0, 1H); 6.50 (d, J = 5.4, 1H); 6.64 (d, J = 5.7, 1H); 7.24 (t, J = 4.8, 1H); 7.43 (dd, J = 2.1, 9.0, 1H); 7.78 (d, J = 2.1, 1H); 8.02 (d, J = 5.7, lH); 8.11 (s, 1H); 8.20 (d, J = 9.3, 1H); 8.38 (d, J = 5.4, 1H). Mass spectrum (ESI) m/e = 390.1 (M+l).

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, 73583-41-2, 4-Bromo-3-chloropyridine.

Reference:
Patent; PRESAGE BIOSCIENCES, INC.; DECKWERTH, Thomas; KLEINMAN, Edward; RUAN, Fuqiang; BAKER, William; KLINGHOFFER, Richard; (126 pag.)WO2016/196393; (2016); A2;,
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. 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3BrClN

Step 2: N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane- 1 ,2-diamine [00252] A mixture of 4-bromo-3-chloropyridine (0.171 g, 0.886 mmol), N1-(2-aminoethyl)- N2-(7-chloroquinolin-4-yl)-N1-methylethane-l,2-diamine (0.247 g, 0.886 mmol), Pd(OAc)2 (22 mg), BINAP (0.12 g), and K3P04 (1.0 g) in 1,4-dioxane (8.9 mL) was degassed with argon for 5 min and then stirred at 100 C for 16.5 h in a sealed tube. The reaction mixture was cooled to room temperature, filtered through Celite, and concentrated in vacuo. Purification by silica gel chromatography using CH2Cl2/CH3OH/NH4OH (270:9: 1, and 180:9: 1) afforded N1-(3-chloropyridin-4-yl)-N2-(2-((7-chloroquinolin-4-yl)amino)ethyl)-N2- methylethane-l,2-diamine (0.276 g, 80%) as a pale-yellow oil, and further lyophilization with CH3CN/H20 gave an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 2.32 (s, 3H); 2.66 (t, J = 6.3, 2H); 2.72 (t, J = 6.6, 2H); 3.26 (q, J = 5.7, 2H); 3.40 (q, J = 6.0, 2H); 6.04 (t, J = 5.0, 1H); 6.50 (d, J = 5.4, 1H); 6.64 (d, J = 5.7, 1H); 7.24 (t, J = 4.8, 1H); 7.43 (dd, J = 2.1, 9.0, 1H); 7.78 (d, J = 2.1, 1H); 8.02 (d, J = 5.7, lH); 8.11 (s, 1H); 8.20 (d, J = 9.3, 1H); 8.38 (d, J = 5.4, 1H). Mass spectrum (ESI) m/e = 390.1 (M+l).

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, 73583-41-2, 4-Bromo-3-chloropyridine.

Reference:
Patent; PRESAGE BIOSCIENCES, INC.; DECKWERTH, Thomas; KLEINMAN, Edward; RUAN, Fuqiang; BAKER, William; KLINGHOFFER, Richard; (126 pag.)WO2016/196393; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dioxane (10 mL), water (2 mL), 4-bromo-3-chloropyridine (111 mg, 0.58 mmol, 1.00 equiv), 6-chloro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)-1H-indole (200 mg, 0.58 mmol, 1.00 equiv), sodium carbonate (122 mg, 1.14 mmol, 2.00 equiv), tetrakis(triphenylphosphane) palladium (66 mg, 0.06 mmol, 0.10 equiv). The resulting solution was stirred overnight at 80 C. in an oil bath. The reaction mixture was cooled. The crude product was purified by Prep-HPLC. This resulted in 28.4 mg (15%) of 6-chloro-5-(3-chloropyridin-4-yl)-2-(trifluoromethyl)-1H-indole as a white solid. (ES, m/z): 329 [M-H]-; (300 MHz, DMSO-d6, ppm): delta 12.66 (brs, 1H), 8.77 (s, 1H), 8.63 (d, J=4.8 Hz, 1H), 7.72 (d, J=6.3 Hz, 2H), 7.49 (d, J=5.1 Hz, 1H), 7.13 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 73583-41-2.

Reference:
Patent; MERIAL, INC.; Meng, Charles; Le Hir de Fallois, Loic; (40 pag.)US2015/366198; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem