Month: April 2022

Electric Literature of 4684-94-0, 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.4684-94-0, name is 6-Chloropicolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

6-Chloropyridine-2-carboxylic acid (1.20 g, 7.62 mmol) and ammonium chloride (0.81 g, 15.2 mmol) were dissolved in DMF (20 mL) and DIPEA (5.31 mL, 30.5 mmol), HONB (2.05 g, 11.4 mmol) and HBTU (4.33 g, 11.4 mmol) were added. The reaction mixture was stirred for 1 h and the solvents were removed in vacuo. The residue was partitioned between DCM (50 mL) and 1 M aq HCl (50 mL) and the aq fraction was extracted with DCM (2*25 mL). The combined organic fractions were washed with sat aq NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from MeOH/water to give the title compound (1.12 g, 94%) as a white solid. LCMS (ES+): 157.4 [MH]+.

Statistics shows that 4684-94-0 is playing an increasingly important role. we look forward to future research findings about 6-Chloropicolinic acid.

Reference:
Patent; Proximagen Limited; Savory, Edward Daniel; Stewart, Allson; Cartey, Allison; Brown, Giles; Simpson, Iain; Oliver, Kathryn; Patient, Lee; Higginbottom, Michael; Cole, Andrew Graham; US2013/289020; (2013); 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. 58484-01-8, name is 3-Amino-2,6-dichloroisonicotinic acid, molecular formula is C6H4Cl2N2O2, 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. Product Details of 58484-01-8

Step 4 : Preparation of 6, 8-dichloro-2- [2- (3-chloro-pyridin -2-yl) -5-trifluoromethyl-2ff-pyrazol-3-yl] -pyrido [3, 4-d] [1, 3] oxazin-4-one; 5-Trifluoromethyl-2- (3-chloro-pyridin-2-yl) -2H-pyrazole-3- carboxylic acid chloride (example 2, step 3) (242 mg) was added to a mixture of 3-amino-2 , 6-dichloroisonicotinic acid (example 1, step 8) (190 mg) in acetonitrile (3 mL) . The mixture was stirred for 5 minutes at room temperature and triethylamine (220 muL) was added and stirred for 20 minutes, before a second portion of triethylamine (220 muL) was added. After the mixture was stirred for further 20 minutes at room temperature, methanesulfonyl chloride (70 muL) was added. After stirring for 2 hours at room temperature, the formed precipitate was filtered off, washed carefully with water and MTB-ether and dried in vacuum to afford 350 mg of the title compound of the formulaas a yellow solid. 1H-NMR (CDCl3, TMS) 6 (ppm) : 7.54-7.57 (2H, m) , 7.88 (IH, s), 8.01-8.04 (IH, m) , 8.56-8.58 (IH, m) .

With the rapid development of chemical substances, we look forward to future research findings about 58484-01-8.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1020253-14-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1020253-14-8 as follows.

This compound (14 mg, 0.026 mmol, 26% yield) as a white solid was prepared in a fashion similar to that described for Example 116, here using 116a (42 mg, 0.101 mmol) and 6-chloro-5-fluoronicotinonitrile (24 mg, 0.151 mmol) as starting materials. LC/MS (ESI+) m/z = 538.1 [M+H]+. NMR (400 MHz, CHLOROFORM-d) delta ppm 8.66 (d, J = 2.54 Hz, 1H) 7.97 – 8.02 (m, 1H) 7.70 (dd, J = 7.14, 2.64 Hz, 1H) 7.58 – 7.65 (m, 1H) 7.1 1 (dd, J = 1 1.54, 8.61Hz, lH) 6.62 (d, J = 14.87 Hz, lH) 6.42 (d, J = 14.87 Hz, 1H) 4.58 – 4.92 (m,2H) 3.54 – 3.75 (m, 8 H) 2.10 (t, J = 8.31Hz, 1H) 1.41 (dd, J = 9.59, 5.87 Hz, 1H) 1.08 (t, J = 6.36 Hz, 1H). N peak was not observed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1020253-14-8, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; CHEN, Jian J.; FROHN, Michael J.; HARRINGTON, Paul E.; LOW, Jonathan D.; MA, Vu V.; NGUYEN, Thomas T.; PICKRELL, Alexander J.; REEVES, Corey; (122 pag.)WO2018/112086; (2018); 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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Bromo-2-chloro-5-methylpyridine

A mixture of 66 (0.35g, 1.02mmol), 4-bromo-2-chloro-5-methylpyridine (0.32g, 1.53mmol) and K3PO4 (0.43g, 2.04mmol) in dioxane (15mL) was exchanged with argon twice, then PdPPh3)4 (0.11g, 0.1mmol) were added to the above mixture. The reaction mixture was heated to 100C and stirred for 4h under argon atmosphere. The mixture was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in 74 petroleum ether 5%) to give the product as a white solid (0.3g, yield=69%). 1H NMR (400MHz, CDCl3) delta 8.25 (s, 1H), 7.64 (m, 2H), 7.19 (s, 1H), 4.07 (d, J=7.0Hz, 2H), 3.99 (dd, J=11.3, 3.2Hz, 2H), 3.35 (td, J=11.8, 2.1Hz, 2H), 2.49 (s, 3H), 2.22-2.16 (m, 1H), 1.60 (s, 9H), 1.50-1.42 (m, 3H). LC/MS (ESI, m/z) 424.14 [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, 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine.

Reference:
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72583-83-6, 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.72583-83-6, name is 1-Methyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine, molecular formula is C7H8N4, molecular weight is 148.17, as common compound, the synthetic route is as follows.

In a vial, to a mixture of intermediate 5 (0.02 g, 0.07 mmol), 7-methoxy-4,5- dihydronaphtho[l,2-d]thiazol-2-amine (0.02 g, 0.07 mmol) was added BOP (0.030 g, 0.069 mmol), DMF (0.3 mL), and DIEA (0.060 ml, 0.35 mmol). After 72 h, the reaction mixture was filtered and subjected to reverse phase HPLC purification to afford Example 1 (4.4 mg, 9.9 %). NMR (500MHz, OMSO-d6) delta 8.34 – 8.04 (m, 2H), 7.85 – 7.81 (m, 1H), 7.80 – 7.73 (m, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.42 – 7.29 (m, 2H), 7.27 – 7.12 (m, 2H), 6.91 – 6.79 (m, 2H), 3.83 (s, 2H), 3.33 (br s, 1H), 3.02 – 2.93 (m, 2H), 2.92 – 2.84 (m, 2H), 3.77 (s, 3H). LCMS m/z = 505.0 (M+H)+; HPLC purity > 96% with retention time 1.81 min. [method A]

The chemical industry reduces the impact on the environment during synthesis 72583-83-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J. P.; (183 pag.)WO2019/14300; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (345.9 mg, 0.888 mmol) and 5-(trifluoromethyl)pyridin-3-amine (120 mg, 0.74 mmol) in pyridine (3 mL) was added POCl3 (227 mg, 1.48 mmol) dropwise. The mixture was stirred at 25 C. for 4 h and at 40 C. for 3 h. Sat. NaHCO3 was added to adjust the pH to 7-8 and the mixture was extracted with ethyl acetate (30 mL*2). The combined organic layers were dried over MgSO4, filtered and the filtrates were concentrated under reduced pressure to afford crude product as a yellow oil. The crude product was then purified by preparative HPLC (37% to 57% (v/v) CH3CN and H2O with 0.05% HCl) to afford 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-N-(5-(trifluoromethyl)pyridin-3-yl)-1H-pyrazole-4-carboxamide (130 mg, 37%). 1H NMR (400 MHz, DMSO-d6) delta ppm 5.67 (d, J=7.28 Hz, 1H), 7.26-7.31 (m, 1H), 7.68 (t, J=7.94 Hz, 1H), 7.94 (d, J=7.50 Hz, 1H), 8.44 (d, J=7.94 Hz, 1H), 8.53 (s, 1H), 8.60 (s, 1H), 8.75 (s, 1H), 9.12 (s, 1H), 11.18 (s, 1H), 11.64 (br d, J=4.63 Hz, 1H). LC-MS: (ES, m/z): [M+1]+ 467.9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 83766-88-5, 2-(tert-Butoxy)pyridine, 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, 83766-88-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 86847-84-9 , The common heterocyclic compound, 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide, molecular formula is C10H13ClN2O, 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 solution of 2-chloro-6pivaloylaminopyridine (10.5 g, 49.528 mmol) in THF (150 mL) is prepared under N2 and cooled to -80 0C. t-BuLi IM in pentane (108.962 mmol, 2.2 equiv.) is added carefully via an addition funnel under rigorously anhydrous conditions, over 1 hour. Once the addition is complete, the mixture is kept at -8O0C for 3 hours, at which point a solution of iodine (15.1 g, 59.431 mmol, 1.2 equiv.) in 50 mL THF under N2, is added slowly in one portion. After the addition, the cooling bath is removed and the reaction mixture allowed to warm up to room temperature under stirring for 2 hours. Finally the reaction mixture is quenched by slowly adding 50 mL of IM HCl. The mixture is then concentrated under vacuum to remove part of the THF, and the residue is partitioned between EtOAc and water. A 10% sodium thiosulfate solution is added until no further decolourisation occurred and that 2 clear phases are visible. The aqueous layer is extracted with EtOAc, the organic layers are gathered, washed with brine, dried over Na2Stheta4, and solvent is removed to afford an oil titrating 65 % of the desired material. This crude is refluxed in 100 mL of IM HCl and is refluxed for 5 hours at which point the depivaloylated product is completely formed. The pH is adjusted to 12 by slow addition OfNaHCO3 and extracted with DCM. The organic layer is concentrated and columned using 7/3 DCM/Cyclohexane as the eluent (Rf 9/21) to afford the title compound as an oil which solidified on standing

The synthetic route of 86847-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2008/65199; (2008); 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. 53710-18-2, name is 3,5-Diiodopyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H3I2N

To a mixture of 4-(3-butenyloxy)-2,6-diethynylpyridine (4, 0.10 g, 0.51 mmol), 3,5-diiodopyridine (6, 0.63 g, 2.0 mmol), Pd(PPh3)4 (24 mg,21 mol), i-Pr2NH (2.5 mL), and THF (20 mL) was added CuI (3.9 mg, 20 mol), and the mixture wasstirred for 5 h at room temperature. The resulting mixture was treated with a Florisil bed and given a rinsewith AcOEt. The filtrate was concentrated by a rotary evaporator and the resulting residue was subjectedto silica gel column chromatography (eluent: CHCl3 to CHCl3/MeOH = 50:1) to give 7 as a colorless solid(0.16 g, 52%). Mp 196-198 C; IR (KBr) 3047, 2925, 2222, 1582, 1550 cm-1; 1H NMR (CDCl3) 2.57-2.64 (m, 2 H), 4.13 (t, J = 6.6 Hz, 2 H), 5.15-5.23 (m, 2 H), 5.82-5.95 (m, 1 H), 7.07 (s, 2 H), 8.21 (s,2 H), 8.73 (s, 2 H), 8.81 (s, 2 H); 13C NMR (CDCl3) 33.2, 67.8, 84.0, 92.1, 92.4, 113.9, 117.9, 120.8, 133.1,143.8, 146.6, 150.7, 155.2, 165.1; HRMS (ESI-TOF) calcd for C23H16I2N3O (M + H+): 603.9383; m/zfound: 603.9362.

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, 53710-18-2, 3,5-Diiodopyridine.

Reference:
Article; Abe, Hajime; Suzuki, Daiki; Shimizu, Ayako; Inouye, Masahiko; Heterocycles; vol. 88; 1; (2014); p. 547 – 557;,
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. 99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below., Recommanded Product: 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

Synthesis of 1,1-dimethylethylcarbamate N-6-chloro-5-(trifluoromethyl)pyridin-3-yl, 6 (0080) (0081) The crude 6-chloro-5-(trifluoromethyl)pyridin-3-amine 5 (1.3 g crude. 6.61 mmol) is dissolved in pyridine (10 ml) and 4-dimethylaminopyridine (DMAP) (50 mg) is added. Di-tert-butyl dicarbonate (2.17 g) is added dropwise and mixture stirred at 22 C. for 4 hours. Toluene (20 ml) is added and all solvents is removed under reduced pressure. The residue is filtered through a plug of silica gel (hexane/ethyl acetate 2:1) to obtain tert-butyl N-6-chloro-5-(trifluoromethyl)pyridin-3-ylcarbamate 6.

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, 99368-68-0, 6-Chloro-5-(trifluoromethyl)pyridin-3-amine.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Jung, Michael E.; Sawyers, Charles L.; Ouk, Samedy; Tran, Chris; Wongvipat, John; (28 pag.)US9388159; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem