Month: March 2022

Application of 886365-46-4, Adding some certain compound to certain chemical reactions, such as: 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid,molecular formula is C7H6ClNO2, 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 886365-46-4.

To the crude tert-butyl ((11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (190 mg, 0.449 mmol) from Step 4 (-2:1 trans/cis mixture) dissolved in DMF (2 ml), was added 5-chloro-3-methylpyridine-2-carboxylic acid (92 mg, 0.538 mmol), pyridine (0.109 ml, 1.346 mmol) and HATU (256 mg, 0.673 mmol) and resulting solution was stirred for 1 hr at RT. The mixture was diluted with EtOAc (8 ml) and saturated NaHCO3 solution (3 ml). Water was added to dissolve precipitated solids. The organic layer was separated, washed with water, brine and concentrated. The residue was and purified by silica gel chromatography on 12 g RediSep Gold column using 10-70% EtOAc in heptane to afford major less polar trans-isomer tert-butyl ((4aR,11bR)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (110 mg, 0.191 mmol, 42.5% yield and more polar minor cis-isomer tert-butyl ((4aS,11bR)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (70 mg, 0.121 mmol, 27% yield).

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. 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
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

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

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

Application of 42373-30-8, 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 42373-30-8, name is 4-Aminonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-aminonicotinaldehyde (57 mg, 0.47 mmol) in tetrahydrofuran was cooled in an ice bath and lithium aluminium hydride (27 mg, 0.70 mmol, 1.5 eq) was added. The ice bath was removed and the reaction mixture was sittred for 30 min. TLC showed complete consumption of starting material. The reaction mixture was quenched with water (1 mL) and 1 N HCI (2 mL) was added extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over MgS04 and concentrated under reduced pressure. The residue was used for the next reaction with in a crude state (60 mg, 99 %).

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 42373-30-8, 4-Aminonicotinaldehyde.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13817; (2013); A1;,
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 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

Reference of 5832-43-9, 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 5832-43-9, name is 4-Methyl-5-nitropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 4-methyl -5-nitropicol i nateTo a solution of 4-methyl-5-nitropicolinic acid (5.0 g, 27.5 mmol) in methanol (60 mL) was slowly added concentrated sulfuric acid (4.39 mL, 82 mmol) and the mixture was refluxed under argon for 18 h. The volatiles were evaporated and a sat. aq. solution of NaHCO3 was added slowly until the aqueous phase showed a pH of 7-8. The resultant mixture was extracted with CH2CI2 (x3), the combined organic extracts were dried (phase separator) and concentrated under vacuum. MS (UPLC-MS): 197.0 [M+H]+, tR (HPLC conditions h): 1.99 mm.

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 5832-43-9, 4-Methyl-5-nitropicolinic acid.

Reference:
Patent; NOVARTIS AG; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; RANDL, Stefan Andreas; VULPETTI, Anna; WO2014/2057; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 823221-93-8 ,Some common heterocyclic compound, 823221-93-8, molecular formula is C6H2BrClF3N, 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 mixture of 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (commercially available) (75 mg, 0.288mmol), 2,2-dimethylpropanamide (32 mg, 0.317 mmol), XantPhos Pd G3 precatalyst (13 mg,0.0 14 mmol), K2C03 (79 mg, 0.57 mmol) in 1 ,4-Dioxane (0.5 mL) was heated at 90C for 0.5hand then 110C for 2h. Purification by reverse phase HPLC delivered product (14 mg, 15%). LC-MS: (positive ES MH+ 281).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823221-93-8, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; PHADTE, Mangala; SONAWANE, Ravindra; HENNESSY, Alan Joseph; MORRIS, James Alan; BOEHMER, Jutta Elisabeth; DESSON, Timothy Robert; GOODWIN-TINDALL, Jake; WO2015/59262; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 914358-72-8 ,Some common heterocyclic compound, 914358-72-8, molecular formula is C6H5BrClN, 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.

Example 60(1r,4r)-6′-(5-Chloro-6-methylpyridin-3-yl)-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine; 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (287 mg, 1.13 mmol), (1r,4r)-6′-bromo-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (Example 19, 213 mg, 0.57 mmol) and potassium acetate (167 mg, 1.70 mmol) and dioxane (3 mL) were added and the mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 (32.4 mg, 0.04 mmol) was added and the mixture was heated to reflux for 1.5 h under N2 atmosphere. 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (120 mg, 0.47 mmol) was added and the reaction was heated to reflux overnight. The volatiles were removed in vacuo and 80 mg of the residue ((1r,4r)-4-methoxy-5”-methyl-6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (MS (ES+) m/z 424 [M+H]+) was mixed with 5-bromo-3-chloro-2-methylpyridine (Intermediate 43, 47 mg, 0.23 mmol), K2CO3 (0.38 mL, 0.76 mmol) and dioxane (2 mL). The mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 adduct (138 mg, 0.19 mmol) was added. The vial was sealed and heated in a microwave reactor at 140 C. for 30 min. EtOAc was added and the mixture was washed with brine and water. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (12 g SiO2, 0-20% MeOH containing 0.1 M NH3 in DCM). The crude product was purified with preparative chromatography. The fractions containing product were combined and concentrated. The water phase was extracted with DCM and the phases were separated using a phase separator. The organic phase was concentrated in vacuo yielding the title compound (5 mg, 6% yield): 1H NMR (CD3OD) delta ppm 1.11 (td, 1H), 1.24-1.43 (m, 2H), 1.49 (td, 1H), 1.63 (td, 2H), 1.90-2.00 (m, 2H), 2.32 (s, 3H), 2.61 (s, 3H), 3.04-3.12 (m, 1H), 3.15 (d, 1H), 3.25 (d, 1H), 3.33 (s, 3H), 6.99 (d, 1H), 7.47 (d, 1H), 7.55 (dd, 1H), 7.99 (d, 1 H), 8.51 (d, 1H); MS (MM-ES+APCI)+ m/z 423 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914358-72-8, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem