Category: 139585-48-1

Reference of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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 100 mL round-bottom flask was charged with NiCl2*6H2O (40 mg, 0.15 mmol) and DMF (10 mL). The resulting solution was stirred and heated to 40 C. Then, 2-chloro-5-methoxypyridine (6,3 mmol), anhydrous LiCl (130 mg, 3 mmol), and zinc dust (230 mg,3.6 mmol) were added. When the temperature rose to 50 C, a grain of iodine crystal and two drops of acetic acid were added to the mixture. The mixture was stirred at 55-60 C until complete conversion of 2-halopyridine (monitored by TLC). To the cooled reaction mixture was added 1 N HCl aqueous solution (5 mL) to consume the remaining zinc dust. The resulting mixture was made alkaline with aqueous ammonia (25%) and diluted with CH2Cl2. The organic layers were collected, dried over anhydrous Na2SO4, concentrated, and purified by column chromatography on silica gel (Hexane/EtOAc 10:1, v/v) to afford desired 5,5′-dimethoxy-2,2′-bipyridine as a light yellow solid, 130 mg, 40% yield. 1H NMR (500 MHz, CDCl3): d 8.33 (d, J 3.0 Hz, 2H, ArH), 8.24 (d, J 9.0 Hz,2H, ArH), 7.30 (dd, J1 9.0 Hz and J2 3.0 Hz, 2H, ArH), 3.91 (s, 6H,2OCH3).

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 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Article; Xu, Bin; Gartman, Jackson A.; Tambar, Uttam K.; Tetrahedron; vol. 73; 29; (2017); p. 4150 – 4159;,
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. 139585-48-1, name is 2-Chloro-5-methoxypyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6ClNO

A solution of 5-(tributylstannyl)thiazole (295 mg, 0.788 mmol) and 2-chloro-5-methoxypyridine (75 mg, 0.526 mmol) in toluene (2.0 mL) was degassed with argon for 3 min. Pd(PPh3)4 (24.29 mg, 0.021 mmol) was added. The reaction mixture was sealed and heated in an oil bath at 105 C for 4 h. After being cooled to room temperature, the reaction mixture was directly loaded on a column for purification. The crude product was purified by flash chromatography (loading in chloroform, 0% to 85% EtOAc in hexane over 10 min using a 4 g silica gel cartridge). The desired fractions were combined and concentrated to yield Intermediate 52A (70 mg, 0.364 mmol, 69.3 % yield) as a white solid.1H NMR (400MHz, METHANOL-d4) delta 8.94 (s, 1H), 8.26 (s, 1H), 8.19 (d, J=2.9 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.36 (did, J=8.7, 3.0 Hz, 1H), 3.88 (s, 3H); LC^MS: method C, RT = 0.64 min, MS (ESI) m/z: 193.3 (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, 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy M.; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; (111 pag.)WO2018/13772; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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. HPLC of Formula: C6H6ClNO

A 50 mL solution of 7-[(5-methoxypyridin-2-yl)acetyl]-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane (2-1c, 1.30 g, 2.50 mmol) in de-oxygenated dioxane (nitrogen stream for 15 minutes) was prepared. A 2M solution of aqueous Na2CO3 solution (30 mL) was made and deoxygenated with a stream of nitrogen for 15 minutes. The above pinacolborate solution (2 mL, 0.1 mmol) was added to a plate of 24 vials containing the appropriate heterohalide; in this case 2-chloro-5-methoxypyridine (14.3 mg, 0.1 mmol). Pd(dppf)Cl2 catalyst (8 mg, 0.009 mmol) was added to each vial. The Na2CO3 solution (1 mL, 2M) was added to each vial using a multipipette. The reaction mixtures were sealed and heated to 110 C. while shaking for 5 hours. The dioxane was removed under vacuum. Ethyl acetate (2 mL) was added to each vial and, after shaking, the aqueous layer was discarded. The ethyl acetate solution was concentrated and the crude material purified directly by preparative HPLC eluting with water/acetonitrile. MS (ES) 499.13 (M+H)+. Retention time: 2.12 minutes XBridge C18 4.6×50 mm 5 um, 5-100% acetonitrile:water (0.1% formic acid).

With the rapid development of chemical substances, we look forward to future research findings about 139585-48-1.

Reference:
Patent; Bhattacharya, Samit K.; Cameron, Kimberly O.; Fernando, Dilinie P.; McClure, Kim F.; Kung, Daniel W.; Londregan, Allyn T.; Simila, Suvi T. M.; US2011/230461; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 139585-48-1, 2-Chloro-5-methoxypyridine, 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, Recommanded Product: 2-Chloro-5-methoxypyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-methoxypyridine

(Step 6) Preparation of 8-(6-tert-butyl-1H-benzo[d]imidazol-2-yl)-4-(5-methoxypyridin-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine [117] To a solution of 4-(5-tert-butyl-1H-benzo[d]imidazol-2-yl)benzene amine 3.1 g (10 mmol) in toluene 10 mL were added 2-chloro-5-methoxy pyridine 1.5 g (10 mmol), Pd(OAc)2 0.1 g (0.5 mmol) and 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl 0.5 g (0.8 mmol) and Cs2CO3 4.6 g (14 mmol), followed by stirring at 90C for 12 hrs. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with ethylacetate. The product thus formed was washed with a saturated sodium bicarbonate solution and a saturated NaCl solution, dried over magnesium sulfate and concentrated in a vacuum. The residue was purified by column chromatography (developing solvent: ethylacetate/hexane=2/3) to give 3.5 g of the title compound (yield 85%).[118] 1H NMR(MeOD-d4) delta : 8.04(d,1H, J=3.0Hz), 7.79(dd, 2H, J=7.8, 1.5Hz), 7.67(d, 1H, J=1.7Hz), 7.56(d, 1H, J=8.6Hz), 7.38(m, 2H), 7.25(d, 1H, J=9.0Hz), 7.17(dd, 1H, J=8.1, 1.4Hz), 6.95(t, 1H, J=8.0Hz), 4.52(t, 2H, J=4.4Hz), 3.99(t, 2H, J=4.4Hz), 3.86(s, 3H), 1.41 (s, 9H)

The synthetic route of 139585-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; KIM, Ji Duck; YOON, Hong Chul; KIM, In Woo; CHO, Min Jae; LEE, In Young; LEE, Sang Ho; PARK, Eun Kyung; LIM, Kwon Jo; NAM, Sang Hyun; WO2012/50380; (2012); 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 139585-48-1, name is 2-Chloro-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6ClNO

Carboxylic acid XIIIAcid XIII-I5 ‘-Methoxy-3,4,5,6-tetrahydro-2H- [ 1 ,2 ‘] bipyridinyl-4-carboxylic acida) 5′-Methoxy-3,4,5,6-tetrahydro-2H-[l,2’]bipyridinyl-4-carboxylic acid ethyl esterTo a stirred solution of piperidine-4-carboxylic acid ethyl ester (0.52 g, 3.34 mmol) and 2- chloro-5-methoxy-pyridine in 10 mL of toluene was added (13 mg, 0.057 mmol) of Pd(II) acetate, (17 mg, 0.027 mmol) of BINAP and tBuOK (0.44 g, 3.90 mmol). The mixture was heated at 1200C for two hours, concentrated under vacuo and the residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1 :2) yielding 0.17 g (24 %) of the title compound as a light yellow oil. ES-MS m/e: 265.3 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 139585-48-1.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JABLONSKI, Philippe; KNUST, Henner; NETTEKOVEN, Matthias; PATINY-ADAM, Angelique; RATNI, Hasane; RIEMER, Claus; WO2011/23626; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 139585-48-1, 2-Chloro-5-methoxypyridine, 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: 139585-48-1, blongs to pyridine-derivatives compound. SDS of cas: 139585-48-1

To a mixture of 2-chloro-5-methoxy-pyridine (6.0 g, 42 mmol) in THF (50 mL) was added lithium diisopropylamide (2.0 M in THF, 42 mL, 83.6 mmol) dropwise at -78 C. The reaction mixture was stirred at -78 C for 1 hour. A.A-di methyl formamide (5.0 mL, 83.6 mmol) was added to the reaction mixture at -78 C, and the mixture was stirred for 1 hour. Saturated NH4Cl solution (100 mL) was added to the reaction mixture. The solution was extracted with EtOAc (200 mL c 2). The combined organic layers were dried over anhydrous Na^SCL and concentrated. The residue was purified by column chromatography on silica gel (0- 25 % EtOAc in petroleum ether) to afford the title compound (5.5 g, 77 %) as a white solid. ‘H NMR (400 MHz, CDCl3) d 10.41 (s, 1H), 8.27 (s, 1H), 7.59 (s, 1H), 4.03 (s, 3H).

The synthetic route of 139585-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 139585-48-1, name is 2-Chloro-5-methoxypyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-5-methoxypyridine

To a 14 mL test tube equipped with a stir bar was added (S)-(5-(1-(tert-butoxy)-2-isopropoxy-2-oxoethyl)-4-(4,4-dimethylpiperidin- 1 -yl)-6-methylpyridin-3 -yl)boronic acid(105 mg, 0.250 mmol), SPhos-Pd-G3 (9.73 mg, 0.0 12 mmol), tribasic potassium phosphate (477 mg, 2.248 mmol) and 2-chloro-5-methoxypyridine (35.9 mg, 0.250 mmol) . The flask was sealed with a rubber septum, then was placed under N2 atm (vac/fill x 3). To the flask was added degassed (N2 bubbling for 5 mm) dioxane (937 .il) and water (312 .il) . The test tube was placed in a 60 C heating block with stirring (t=0). The reaction was stirred for 3 hours. The reaction was cooled to RT and diluted withwater and EtOAc. The organic layer was washed with brine, collected, dried over MgSO4, filtered and hte volatiles evaporated to afford the cmde product. The crude product was purified on silica gel (24 g column, 20-100% EtOAc:Hex) to afford the product isopropyl (S)-2-(tert-butoxy)-2-(4?-(4,4-dimethylpiperidin- 1 -yl)-5 -methoxy-6?-methyl-[2,3 bipyridinj-5?-yl)acetate (22 mg, 0.045 mmol, 18.21 % yield) as a brown oil. ESI-MS(+)m/z = 484.3 (M+1).

The synthetic route of 139585-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine. A new synthetic method of this compound is introduced below.

To a 10 mL microwave tube was added sodium tert-butoxide (0.105 mL, 0.856 mmol), [dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine]2-(2-aminoethyl)phenyl)palladium(II) chloride (15.54 mg, 0.019 mmol), 2-chloro-5-methoxy-pyridine (61.5 mg, 0.428 mmol), 1-(trans-3-aminocyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (intermediate 26, 90 mg, 0.389 mmol) and dry dioxane (1 mL) and it was sealed under argon. The mixture was stirred at 110 C. for 2 hours. The vial was opened and the reaction mixture evaporated to dryness under reduced pressure. Purification using reverse phase HPLC gave 1-(trans-3-(bis(5-methoxypyridin-2-yl)amino)cyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (62 mg, 0.139 mmol, 35% yield). M+1: 446.1. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.35 (s, 6H) 2.47-2.61 (m, 2H) 3.20-3.33 (m, 2H) 3.83 (s, 6H) 4.97-5.14 (m, 1H) 5.20-5.33 (m, 1H) 6.83 (d, J=8.77 Hz, 2H) 6.92 (dd, j=7.16, 5.26 Hz, 1H) 7.17 (dd, J=8.84, 3.14 Hz, 2H) 7.39 (dd, J=7.16, 1.61 Hz, 1H) 8.10 (d, J=2.92 Hz, 2H) 8.17 (dd, J=5.26, 1.61 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139585-48-1, 2-Chloro-5-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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.

Step 2; 2-(5-methoxy-pyridin-2-yl)-benzoic acid diethylamide; Under an argon atmosphere, a mixture of tripotassium phosphate (6.24 g) and water (15 ml) was added to a mixture of 2-chloro-5-methoxy-pyridine (2.05 g), 2-(diethylcarbamoyl)benzeneboronic acid (4.65 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride-dichloromethane complex (0.584 g) and toluene (30 ml), and the mixture was stirred at 80 C. for 2 hr. The reaction mixture was cooled to room temperature, water (20 ml), citric acid (2.2 g) and ethyl acetate were added and the mixture was stirred and filtered through celite. The filtrate was partitioned in a separatory funnel. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/2) to give a roughly purified product (1.144 g) of the title compound. This product was directly used for the next reaction without further purification.1H-NMR (CDCl3) delta: 8.33 (1H, d, J=2.9 Hz), 7.68 (1H, dd, J=7.7, 1.3 Hz), 7.60 (1H, d, J=8.6 Hz), 7.48-7.32 (3H, m), 7.25-7.15 (1H, m), 3.88 (3H, s), 3.32-2.78 (4H, m), 1.07 (3H, t, J=7.1 Hz), 0.81 (3H, t, J=7.2 Hz).

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 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Patent; JAPAN TOBACCO INC.; US2010/240634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem