Tag: M.W:100-200

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

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 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

Synthetic Route of 934180-48-0, 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. 934180-48-0, name is 4-Chloro-2-methoxy-3-nitropyridine, molecular formula is C6H5ClN2O3, 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.

3-chloro-5-cyanophenol (4.73 g, 1.00 equiv) and potassium carbonate (8.52 g, 2.00 equiv) were added to a solution of nitro compound from the previous step (5.81 g, 30.8 mmol) in DMF (90 mL). After heating for 20 hrs at 50 C. the reaction mixture was cooled to rt, and poured into water (500 mL). The mixture was extracted with ether, washed with water and brine, dried over MgSO4, and concentrated in vacuo to give crude material (10 g) which was carried on to the next step.

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 934180-48-0, 4-Chloro-2-methoxy-3-nitropyridine.

Reference:
Patent; Roche Palo Alto LLC; US2010/56535; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 88511-57-3, 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 88511-57-3, name is 4-Amino-3-nitropyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

3d) 3,4-diamino-2-hydroxypyridine 11.0 g (71 mmol) of 4-amino-2-hydroxy-3-nitropyridine were dissolved in 150 ml of dimethylformamide and reduced by catalytic hydrogenation at ambient temperature (Pd/C 10%). Yield: 83% of theory. C5H7N3O (125.13) Mass spectrum: (M+H)+=126

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 88511-57-3, 4-Amino-3-nitropyridin-2(1H)-one.

Reference:
Patent; Boehringer Ingelheim Pharma GmbH Co. KG; US2005/20574; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13362-30-6, 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 13362-30-6 as follows.

To a solution of ethyl 2-aminoisonicotinate (15.45 g, 92.97 mmol) in tetrahydrofuran (300 mL) were added triethylamine (32.22 mL, 232.43 mmol), di-tert-butyl bicarbonate (50.73 g, 232.43 mmol) and 4-dimethylaminopyridine (1.14 g, 9.30 mmol), and the resulting mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-0/100) to give the title compound (20.35 g, yield 60%) as colorless crystals.1H NMR (CDCl3) delta 1.42 (3H, t, J=7.2 Hz), 1.45 (18H, s), 4.42 (2H, q, J=7.2 Hz), 7.77 (1H, d, J=5.1 Hz), 7.81 (1H, s), 8.61 (1H, d, J=5.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13362-30-6, its application will become more common.

Reference:
Patent; Itoh, Fumio; US2010/69381; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67058-77-9 , The common heterocyclic compound, 67058-77-9, name is 3-Nitro-1H-pyrrolo[2,3-c]pyridine, molecular formula is C7H5N3O2, 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.

To a solution of 3 -nitro- 1H-pyrrolo [2,3 -c]pyridine (250 mg, 1.53 mmol) in DIVIF (5 mL) was added NaH (60% dispersion in mineral oil, 61 mg, 1.53 mmol). After stirred at 0 C for 10 mm, the mixture was added dimethylsulfate (193 mg, 1.53 mmol) dropwise. After stirred at 0 C for 3 hrs, the mixture was partitioned in a mixture of H20 (50 mL) and EA (50 mL). The aqueous phase was then extracted by EA (50 mL x 2). Organic phase was combined, dried over anhydrous Na2SO4, and evaporated in vacuum. The residue was washed with MeOH (5 mL) to afford 6-methyl- 3-nitro-6H-pyrrolo[2,3-c]pyridine (70 mg, 26%) as a yellow solid. ?H NIVIR (400 IVIHz, DMSO-d6):oe = 9.09 (s, 1H), 8.65 (s, 1H), 8.25 (dd, J 6.8, 1.2 Hz, 1H), 8.14 (d, J= 6.8 Hz, 1H), 4.26 (s, 3H). MS: m/z 178.0 (M+H).

The synthetic route of 67058-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0, 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.628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, molecular weight is 175.55, as common compound, the synthetic route is as follows.

1.15.1. Step i: tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate1002621 Diphenylphosphoryl azide (DPPA) (129 mmol) was added to a mixture of 2-chloro-3-fluoro- pyridine-4-carboxylic acid (85.7 mmol), Et3N (257 mmol) in 1:1 tert-BuOH/toluene (200 mL). The mixture was heated at 110C for 4 h. Mixture was diluted with H20 and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (Si02, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro- 3 -fluoro-4-pyridyl)carbamate.

The chemical industry reduces the impact on the environment during synthesis 628691-93-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; BLANC, Javier; OR?ULIC, Mislav; RO?CIC, Maja; WO2015/110378; (2015); A1;,
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. 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate. A new synthetic method of this compound is introduced below., Recommanded Product: 868551-30-8

Example 75A: 2~(4~Methyl~5~nitro^yridin-2-yl)~chromen-4-one O-tert- butyl-oximeA solution of 2′-hydroxyacetophenone (1.68 g, 12.39 mrrtol) in tetrahydrofuran (120 mi) under argon was cooled to -78C and treated dropwise with lithium hexamethyldisilazane (1 M in tetrahydrofuran, 2.25 ml, 2.25 mmol). The solution was stirred at -78C for 1 hour and at -10C for 2 hours then cooled down to -78C and treated dropwise with a solution of 4- efhy.-5-nitro-pyridine-2-carboxylic acid methyl ester (WO2005/103003) (2.42 g, 12.39 mmo.) in tetrahydrofuran (60 ml). The dark red solution was stirred at -78C for 1 hour then at room temperature for 18 hours. The mixture was poured into a ice-cold 1 N solution of hydrochloric acid (200 ml) and extracted several times with ethyl acetate. The combined extracts were dried over sodium sulfate and concentrated to dryness. The residue was dissolved in acetic acid (60 ml), treated with sulfuric acid (0.33 ml) and heated to 100X for 30 minutes. After cooling to room temperature, the solution was concentrated and the residue added with water and neutralized with a saturated solution of sodium hydrogenocarbonate. The precipitate was filtrated, washed with water and dried under vacuum to yield 2-(4- Methyl-5-nitro-pyridin-2-yl)-chromen-4-one (2.33 g, 66%) as a brown solid. The previous chromen-4-none (770 mg, 2.72 mmol) was treated with tert-buty.- hydroxylamine hydrochloride (685 mg, 5.45 mmol) in methanol (20 ml) at 130C for 30 minutes under microwave irradiation (method D, step 1) to yield the title compound (394 mg, 41 %) after purification by silica ge. flash chromatography (gradient cyciohexane/dichloromethane 0-80%) as a gold solid.1 H NMR: (300 MHz) DMSO-d6 delta (ppm): 9.23 (s, 1 H), 8,08 (dd, J = 7.9 Hz, J = 1.7 Hz, 1 H), 7.89 (s, 1 H), 7.78 (s, 1 H), 7.42 (td, J = 7.6 Hz, J = 1.7 Hz, 1 H), 7.32-7.19 (m, 2H), 2.76 (s, 3H), 1.42 (s, 9H).

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, 868551-30-8, Methyl 4-methyl-5-nitropicolinate.

Reference:
Patent; DOMAIN THERAPEUTICS; PRESTWICK CHEMICAL, INC.; SCHANN, Stephan; MAYER, Stanislas; MORICE, Christophe; GIETHLEN, Bruno; WO2011/51478; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 121643-44-5 , The common heterocyclic compound, 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5- dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield). 1 H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

The synthetic route of 121643-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem