Tag: M.W:200-300

Application of 116355-18-1, 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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine. A new synthetic method of this compound is introduced below.

EtOH (1.8 mL) was added into a mixture of 4-bromo-3-ethylpyridinehydrobromide (49 mg, 0.18 mmol), B2(OH)4 (49 mg, 0.55 mmol), XPhos-Pd-G2 (14 mg, 0.018 mmol), XPhos (17 mg, 0.037 mmol), and KOAc (54 mg, 0.55 mmol). The reaction was degassed via N2 and stirred at 80C overnight. After cooling to room temperature, solutions of N-(2-(3-bromophenyl)propan-2-yl)-2-(trifluoromethyl)benzenesulfonamide (Intermediate 1J) (100 mg, 0.24 mmol) in EtOH/THF (0.3 mL/0.3 mL) and K2C03 (1.8 M, 0.31 mL, 0.55 mmol) were added respectively into the reaction. The mixture was degassed via N2 again and stirred at 85C overnight. The reaction was cooled to room temperature, filtered through celite, washed with EtOAc (3X), and concentrated in vacuo to give a residue which was dissolved into EtOAc. This solution was washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by MS-HPLC to afford the title compound (16 mg, 20%). LCMS (method A): m/z 449.3 (M+H)+. NMR (CDC13) delta 8.54 (s, 1H), 8.46 (d, 1H), 7.83 (d, 1H), 7.79 (d, 1H), 7.59 (t, 1H), 7.47 (t, 1H), 7.31 (m, 2H), 7.21 (t, 1H), 7.11 (dt, 1H), 7.03 (d, 1H), 5.28 (s, 1H), 2.63 (q, 2H), 1.69 (s, 6H), 1.13 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116355-18-1, 6-Bromo-7-methylimidazo[1,2-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 188057-20-7, 4-Iodopyridin-3-ol, 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: 4-Iodopyridin-3-ol, blongs to pyridine-derivatives compound. Recommanded Product: 4-Iodopyridin-3-ol

Dry DMF (6.0 mL) was added to methyl 4-hydroxy-3-iodobenzoate (0.56 g, 2.0 mmol), ethynylboronic acid MIDA ester (0.47 g, 2.6 mmol), CuI (38 mg, 0.20mmol), PdCl2(Ph3P)2 (70 mg, 0.10 mmol) and Ph3P (52 mg, 0.20 mmol) under N2. 1,1,3,3-Tetramethylguanidine(TMG) (0.30 mL, 2.4 mmol) was added to the resulting solution under N2. The reactionmixture was stirred at 50 Cfor 22 h under N2. The resulting mixture was diluted with water to form aprecipitate, which was filtered, washed with water and dried at room temperature. The obtained solid was dissolved in acetone and purified by flash chromatography (SiO2, CH2Cl2 : MeOH = 10 : 1). The eluted material was washed with hot EtOH and dried to give 1A (493.6 mg, 75%) as a pale brown solid; Furo[2,3-c]-2-boronic acid (14): Prepared from 3-hydroxy-4-iodopyridine and ethynylboronic acidMIDA ester. The resulting mixture was diluted with water and extracted with AcOEt. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2,CH2Cl2 : MeOH = 10 : 1) to give 262.4 mg of 1 : 1 mixture of MIDA boronate and boronic acid as a pale yellow powder. The mixture was treated with hot EtOH to afford 14 (216.4 mg, 66%) as a pale yellowsolid; IR (cm-1) 3006, 1734, 1683, 1608, 1473, 1373, 1322, 1259, 1216, 1159, 1093, 1016; 1H-NMR(DMSO-d6) delta 7.50 (d, J = 1.0 Hz, 1H), 7.74 (dd, J = 1.0 Hz, 5.0 Hz, 1H), 8.37 (d, J = 5.0 Hz, 1H), 8.96(brs, 1H); HRMS calcd for C7H7NO3B [M+H] 164.0514, found 164.0514 (Delta 0.07).

The synthetic route of 188057-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakurai, Yohji; Heterocycles; vol. 94; 7; (2017); p. 1322 – 1336;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 20511-12-0, 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 20511-12-0, name is 5-Iodopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-iodopyridin-2-amine (25.0 g, 113 mmol) in acetonitrile (500 m was added NBS (20.2 g, 113 mmol) slowly at room temperature. After the addition, the reaction mixture was stirred at room temperature for a further 72 h. The solvent was evaporated at 40C at reduced pressure and the residue was purified by column chromatography (silica gel, 200 – 300 mesh, ethyl acetate / petroleum ether 3: 1, v/v) to give 3-bromo-5-iodopyridin-2-amine (15.9 g, 47 %) as a yellow solid. 1H NMR (300MHz, DMSO): delta 8.07 (s, 1H), 7.98 – 7.97 (m, 1H), 6.43 (brs, 1H). LC/MS: 298.9 [M+H]+.

According to the analysis of related databases, 20511-12-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; PADILLA, Fernando; WANNER, Jutta; XIE, Wenwei; ZHANG, Xiaohu; WO2012/163724; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6318-51-0, Adding some certain compound to certain chemical reactions, such as: 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone,molecular formula is C12H8ClNO, 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 6318-51-0.

General procedure: Six variants with significantly improved activity were selected to test their stereoselectivity and conversion rate. Bioconversion was conducted with 20mM 1a-9a, 20UmL-1 KpADH or variants in PBS buffer (pH 7.0, 100mM) in total volume of 2mL at 30C and 180rpm overnight. Then, 1mL of the reaction mixture was withdrawn and extracted with equal volume of ethyl acetate. The organic phase was isolated by centrifugation at 12000×g for 2min, and dried over anhydrous MgSO4. The conversion rate and stereoselectivity of the products were determined using the Agilent 1100 equipped with a Chiralcel OB-H column or a Chiralcel OD-H column (0.46mm×250mm×5mum, Diacel, Japan). Detailed conditions for stereoselectivity analysis and the retention times of (R)- and (S)-alcohols could be found in Table S3 [28].

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Guochao; Dai, Wei; Wang, Yue; Zhang, Lu; Sun, Zewen; Zhou, Jieyu; Ni, Ye; Molecular catalysis; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 909717-95-9, Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Example 47 4-hydroxypyrazolo[1,5-a]pyridine The compound of Example 23 (4.30 g) was dissolved in dichloromethane (50 mL) in an argon atmosphere. While the solution was kept at 0 C., boron tribromide (1.0 mol/L dichloromethane solution, 23.4 mL) was added and the mixture was stirred for 1 hour. Additional boron tribromide (23.4 mL) was then added and the mixture was stirred at room temperature for another 3 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give a yellow powder (4.80 g). To this product, 47% hydrobromic acid (100 mL) was added and the mixture was stirred for 5 hours under reflux. Subsequently, the mixture was made basic by adding sodium hydroxide and then made acidic again by adding hydrochloric acid. The mixture was extracted three times with ethyl acetate and the organic layer was washed with saturated brine and dried over sodium sulfate. Evaporating the solvent under reduced pressure afforded the title compound as a yellow powder (2.10 g) (Process C). 1H-NMR (CDCl3, 400 MHz) delta 5.76 (1H, brs), 6.47 (1H, d, J=7.3 Hz), 6.62-6.65 (2H, m), 7.92 (1H, d, J=2.4 Hz), 8.17 (1H, d, J=6.7 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,909717-95-9, Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Kohno, Yasushi; Adams, David Roger; Ando, Naoki; US2008/207902; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 866775-18-0 , The common heterocyclic compound, 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, 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.

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate 3D) (100 mg, 0.334 mmol) was dissolved in 5M HCI (2.5 ml) and heated at 150C, 5.5 bar in the microwave for 1 hour. The reaction mixture was purified by reverse phase chromatography eluting with water/MeCN to afford the title compound. MS m/z 241 [M+H]+. 1H NMR (400 MHz, DMSO – d6) delta 13.33 (1 H, br hump), 7.79 (1 H, s), 7.19 (2H, br s

The synthetic route of 866775-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77199-09-8, 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.77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.

General procedure: A mixture 2a or 2b (1 g, 1 equiv.), anappropriate pinacol boronate ester (1.2 equiv.), [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex withdichloromethane (10 mol %), cesium carbonate (2.0 equiv.), 1,4-dioxane (8 ml) and water (4 ml) was sealed in a 20 ml microwavereaction vial (Biotage). The vial was irradiated in a microwaveapparatus at 110 C, normal absorption for 30-90 min. The reactionmixture was cooled to room temperature and work up was performedas described in method 1 to obtain the esters 4b-i.

Statistics shows that 77199-09-8 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-bromopicolinate.

Reference:
Article; Tung, Truong Thanh; Jakobsen, Tim Holm; Dao, Trong Tuan; Fuglsang, Anja Thoe; Givskov, Michael; Christensen, S°ren Br°gger; Nielsen, John; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1011 – 1020;,
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. 913836-16-5, name is 5-Bromo-2-hydroxyisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrNO3

[0717] XXV-6 was obtained following the synthetic scheme as described above. MS (ES) m/z (M+H) 231.95.

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, 913836-16-5, 5-Bromo-2-hydroxyisonicotinic acid.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1003711-85-0, 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.1003711-85-0, name is 5-Bromo-4-chloro-2-methylpyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

4-Chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-5-(4,4,5,5- tetramethyl-[1 ,3]dioxolan-2-yl)-benzenesulfonamide (57 mg, 0.125 mmol), 5-bromo-4- chloro-2-methyl-pyridine (21 mg, 0.1 mmol), Pd(Ph3P)4 (12 mg, 0.01 mmol), K2CO3 (69 mg, 0.5 mmol) in a mixture of dioxane (1.5 ml.) and water (0.15 ml.) was degassed with N2 for 5 min. The reaction vessel was sealed and heated at 85 0C for 14 hrs. After the filtration, the mixture was purified by prep. LCMS to afford 4-chloro-5-(4- chloro-6-methyl-pyridin-3-yl)-2-fluoro-N-(2-methoxy-phenyl)-N-methyl- benzenesulfonamide 3-1. MS: 454.7 (M+H)+; tR = 7.77 min (method 2). NMR (CDCI3), delta, 8.350 (1 H, s), 7.549(1 H, d, J=6.9Hz), 7.257-7.436 (5H, m), 6.932 (1 H, m), 6.817 (1 H, m), 3.513 (3H, s), 3.389 (3H, d, J=2.1 Hz), 2.656 (3H, s).

The chemical industry reduces the impact on the environment during synthesis 1003711-85-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.54232-43-8, name is 6-Bromo-5-methoxypicolinic acid, molecular formula is C7H6BrNO3, molecular weight is 232.03, as common compound, the synthetic route is as follows.Formula: C7H6BrNO3

[0126] 6-Bromo-5-methoxypicolinic acid (XXXXVI) (665 mg, 2.87 mmol) was dissolved in 10 ml of dichloromethane. N,O-dimethylhydroxyamine hydrochloride (336 mg, 3.44 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (659 mg, 3.44 mmol), 4-dimethylaminopyridine (DMAP) (105 mg, 0.86 mmol), and triethylamine (TEA) (479 mul, 3.44 mmol) were added to the resulting solution and the solution was stirred at room temperature for 16 hrs. And then, the solution was extracted with 30 ml of dichloromethane and 30 ml of water. The organic layer was treated with magnesium sulfate (MgSO4) and filtered, and the solution was concentrated and purified by silica gel column chromatography (normal hexane : ethylacetate = 3 : 1, v/v) to give the title compound as colorless crystals (515 mg, 1.87 mmol, 65 %). 1H NMR (400 MHz, CDCl3) delta 7.70 (d, J = 8.4 Hz, 1H), 7.17 (d, J = 8.4 Hz, 1H), 3.93 (s, 3H), 3.81 (s, 3H), 3.36 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54232-43-8, 6-Bromo-5-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem