Tag: M.W:200-300

Reference of 53937-02-3, 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. A new synthetic method of this compound is introduced below.

tert-Butyl 2-bromo-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (0.73 g, 2.0 mmol), 4-benzyloxy pyridinone (0.44 g, 2.2 mmol), and Cs2CO3 (0.72 g, 2.2 mmol) were suspended in DMSO (12 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar, and 8-hydroxyquinoline (87 mg, 0.60 mmol) and copper iodide (0.49 g, 2.6 mmol) were added to the suspension. The evacuation/Ar flushing process was repeated twice more, and the reaction mixture was heated at 130 C. for 18 h under N2. The mixture was cooled, diluted with 5.0:3.5:1.5 NH4Cl(aq.)/NH4OH/H2O (70 mL), and the resulting suspension was stirred at ambient temperature for 30 min. The resulting solids were collected by filtration, dissolved in CH2Cl2 (30 mL) and washed with 5.0:3.5:1.5 NH4Cl(aq.)/NH4OH/H2O (2*30 mL). The resulting organic solution was dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. Flash chromatography (40 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 2 column volumes, increased to 50:50 over 12 column volumes and held for 5 column volumes; increased to 0:100 over 10 column volumes and held for 5 column volumes) gave the title compound (0.51 g, 52%) as a yellow foam: 1H NMR (500 MHz, DMSO-d6) delta 8.00 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.50-7.36 (m, 5H), 7.29 (d, J=8.0 Hz, 1H), 6.15 (dd, J=8.0, 2.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 5.16 (s, 2H), 4.57 (s, 2H), 3.75 (t, J=5.5 Hz, 2H) 3.67 (s, 3H), 2.88 (t, J=5.5 Hz, 2H), 1.42 (s, 9H); ESI MS m/z 487 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, and friends who are interested can also refer to it.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2012/157460; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-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, Application In Synthesis of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

4-(6-Amino-pyridin-3-yl)-piperazine-1 -carboxylic acid fe/t-butyl ester (2.50 g, 8.98 mmol) in DCM (30 mL) and 4M HCI in 1 ,4-dioxane (1 1.2 mL, 44.9 mmol) is stirred for 16 h at rt. The reaction mixture is filtered and washed with ether to give the title compound. (0452) Yield: 2.23 g (99%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; SMITH KEENAN, Lana Louise; LOWE, Michael D.; RAZAVI, Hossein; SARKO, Christopher Ronald; SURPRENANT, Simon; TAKAHASHI, Hidenori; TURNER, Michael Robert; WU, Xinyuan; (182 pag.)WO2019/81637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 94446-97-6, 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. 94446-97-6, name is 2-Bromo-3-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

Under argon and in anhydrous medium, the aminocompound 3 (340 mg, 1.25 mmol) was dissolved in DMF (10 mL). At 0 C, 60% NaH (73 mg, 1.5 mmol) was added slowly. The mixture was stirred for 30 min at 0 C. Then, 2-bromo3-bromomethylpyridine (Rebek et al., 1985) (380 mg, 1.5 mmol) in DMF (10 mL) was added. The mixture was stirred 4 h at room temperature. The solvent was removed in vacuo, and the residue was quenched with H2O (25 mL). The aqueous mixture was extracted with ethyl acetate (20 mL), and the combined organic extract was washed several times with H2O, then dried over MgSO4. After concentration under reduced pressure, the crude mixture was purified by flash chromatography over silica gel (eluent: petroleum ether, ethyl acetate, 1:1) to give compound 4 as a white solid (347 mg, 64%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,94446-97-6, its application will become more common.

Reference:
Article; Boutin, Jean A.; Bouillaud, Frederic; Janda, Elzbieta; Gacsalyi, Istvan; Guillaumet, Gerald; Hirsch, Etienne C.; Kane, Daniel A.; Nepveu, Francoise; Reybier, Karine; Dupuis, Philippe; Bertrand, Marc; Chhour, Monivan; Le Diguarher, Thierry; Antoine, Mathias; Brebner, Karen; Da Costa, Herve; Ducrot, Pierre; Giganti, Adeline; Goswami, Vishalgiri; Guedouari, Hala; Michel, Patrick P.; Patel, Aakash; Paysant, Jerome; Stojko, Johann; Viaud-Massuard, Marie-Claude; Ferry, Gilles; Molecular Pharmacology; vol. 95; 3; (2019); p. 269 – 285;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1083057-14-0, 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 1083057-14-0 as follows.

Tert-butyl 3-(6-amino-3-methylpyridin-2-yl) benzoate (3. 0 g) was added to 47% aqueous solution of hydrogen bromide (15 mL) portion wise at 27C in 15 minutes. The reaction mixture was cooled to -20C and bromine (1 .52 mL) was added drop wise. Stirred the reaction mixture at -20C for 90 minutes and sodium nitrite solution (1 .96 g in 7.5 mL of water) was added for 20 minutes at the same temperature. Reaction mixture was warmed to 15C and stirred for 1 hour and 45 minutes at the same temperature. Again cooled the reaction mixture to -20C and sodium hydroxide solution (8.44 g in 30 mL of water) was added slowly. The reaction mass was extracted with ethyl acetate (3 x 50 mL) and dried over sodium sulfate. The solution was concentrated under reduced pressure to obtain crude product. The crude product was purified by column chromatography using (10% to 50%) ethyl acetate / hexane as eluent to obtain 185 mg of tert-butyl 3-(6- bromo-3-methylpyridin-2-yl)benzoate as a colorless liquid with 96.07% purity by HPLC and 1 .0 g of 3-(6-bromo-3-methylpyridin-2-yl)benzoic acid as a white solid with 98.36% purity by HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1083057-14-0, its application will become more common.

Reference:
Patent; DR. REDDY?S LABORATORIES LIMITED; DAHANUKAR, Vilas Hareshwar; ORUGANTI, Srinivas; RAO, Pallavi; CHAKKA, Ramesh; BAIG, Mohammed Azeezulla; VYALA, Sunitha; SALADI, Venkata Narasayya; PEDDY, Vishweshwar; ELATI, Raviram Chandrasekhar; MOHANARANGAM, Saravanan; RAJ, Gopal; MAMIDIPALLI, Phani; (73 pag.)WO2017/175161; (2017); 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. 630120-99-9, name is 5-(Benzyloxy)-2-bromopyridine, molecular formula is C12H10BrNO, 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. Quality Control of 5-(Benzyloxy)-2-bromopyridine

Palladium acetate (0.43 g, 1.89 mmol), l,l’-bis(diphenylphosphino)ferrocene(2.10 g, 3.79 mmol), and triethylamine (11. 1 ml, 80.0 mmol) were added to a methanol solution (200 ml) of 5-(benzyloxy)-2-bromopyridine (10.0 g, 37.8 mmol) under carbon monoxide atmosphere, this mixture was stirred for 2 days at 9O0C. This reaction solution was cooled to room temperature, followed by concentrating this solvent under reduced pressure and purifying the obtained residue by silica gel column chromatography (Flash cartridge 65M, hexane:ethyl acetate=l :1) to obtain methyl 5-(benzyloxy)pyridin-2-carboxylate (7.48 g, yield: 81%) as an ecru solid.

With the rapid development of chemical substances, we look forward to future research findings about 630120-99-9.

Reference:
Patent; BANYU PHARMACEUTICAL CO.,LTD.; IINO, Tomoharu; ASAI, Masanori; OHNO, Akio; IF2; ISHIKAWA, Makoto; OHTAKE, Norikazu; WO2010/24110; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 96568-04-6, 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.96568-04-6, name is Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate, molecular formula is C10H8Cl2FNO3, molecular weight is 280.08, as common compound, the synthetic route is as follows.

Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (40 g) and triethyl orthoformate (26.1 mL) in acetic anhydride (100 mL) were stirred at 85 C. for 6.5 hours, cooled, and concentrated. The concentrate was crystallized from hexanes with a small amount of diethyl ether and dichloromethane.

Statistics shows that 96568-04-6 is playing an increasingly important role. we look forward to future research findings about Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate.

Reference:
Patent; Hinman, Mira M.; Rosenberg, Teresa A.; Wagner, Rolf; US2005/234053; (2005); 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 73290-22-9, name is 2-Bromo-5-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H3BrIN

General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2¡Á20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5% EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98%).

With the rapid development of chemical substances, we look forward to future research findings about 73290-22-9.

Reference:
Article; Rao, Maddali L.N.; Dhanorkar, Ritesh J.; Tetrahedron; vol. 71; 2; (2015); p. 338 – 349;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 152460-10-1 ,Some common heterocyclic compound, 152460-10-1, molecular formula is C16H15N5, 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.

General procedure: The final target compounds were synthesized from 6-methyl-N-(4-(pyridin-3-yl) pyrimidin-2-yl) benzene-1,3-diamine 8(2 mmol), DMF (10 mL), and DIPEA (4 mmol) followed by substituted aromatic acid (2 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction mixture was poured into ice-cold water. The obtained yellow precipitate washed with water and dried to get target titled product pyrimidine scaffold benzamide derivatives (9 a-k).

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. 152460-10-1, N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Thirumurugan; Lakshmanan, Sivalingam; Govindaraj, Dharman; Daniel Prabu, D. Sam; Ramalakshmi; Arul Antony; Journal of Molecular Structure; vol. 1171; (2018); p. 541 – 550;,
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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-2-methoxynicotinic acid

PREPARATION J In a 50 ml. round-bottomed reaction flask equipped with stirring bar and reflux condenser, there were placed 1.0 g. (0.0043 mole) of 5-bromo-2-methoxynicotinic acid (the product of Preparation I) and 10 ml. of methanol, followed by 50mul. of concentrated sulfuric acid. The resulting reaction mixture was then refluxed for a period of approximate 16 hours (i.e., overnight). Upon completion of this step, the mixture was cooled to room temperature (~20C.) and filtered, and the recovered precipitate was dried to constant weight to ultimately yield 695.8 mg. (66%) of pure methyl 5-bromo-2-methoxynicotinate (m.p. 90-101C.) in the form of a fluffy white solid. The pure product was further characterized by means of nuclear magnetic resonance data.

The synthetic route of 54916-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goldstein Steven Wayne; Sarges Reinhard; EP306251; A2; (1989);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-50-3, 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.39856-50-3, name is 5-Bromo-2-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

To a solution of 5-bromo-2-nitropyridine (40.0 g,197 mmol) in DMSO (150 mL) were added 1-Bocpiperazine(47.4 g, 252 mmol) and DIPEA (38 mL,219 mmol) . The reaction mixture was heated at 80 C for11 h. The reaction mixture was poured into ice-water andthen extracted with EtOAc. The combined extracts werewashed with water and brine. The organic layer was driedover Na2SO4, filtered, and concentrated under reducedpressure. Purification by column chromatography (1:9methanol/ dichloromethane) gave 1-Boc- 4-(6-nitro-pyridin-3-yl)-piperazine (49.9 g, 82%) as yellow solid. 1H NMR(400 MHz, CDCl3): delta 8.11 (d, J = 9.1 Hz, 1H), 8.08 (d, J =2.7 Hz, 1H), 7.18 (dd, J = 9.1, 2.8 Hz, 1H), 3.65-3.56 (m,4H), 3.48-3.38 (m, 4H), 1.45 (s, 9H).

Statistics shows that 39856-50-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-nitropyridine.

Reference:
Article; Guo, Qingxiang; Li, Yongtao; Zhang, Chao; Huang, Zhi; Wang, Xin; Nie, Yongwei; Li, Yao; Liu, Yanhua; Yang, Shengyong; Xiang, Rong; Fan, Yan; Medicinal Chemistry Research; vol. 27; 6; (2018); p. 1666 – 1678;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem