Tag: M.W:200-300

Application of 169833-70-9, Adding some certain compound to certain chemical reactions, such as: 169833-70-9, name is 6-Bromo-2-chloropyridin-3-amine,molecular formula is C5H4BrClN2, 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 169833-70-9.

31.4 g 6-bromo-2-chloro-pyridin-3-amine (151.3 mmol) was dissolved in 200 ml glacialacetic acid, 15 mL acetic anhydride (158.9 mmol) was added to this solution dropwise and the reaction mixture was stirred at room temperature until no further conversion was observed. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the organic phase was washed with 10% aqueous K2C03 and brine. Following drying over Na2SO4 removal of the solvents under reduced pressure gaveN-(6-bromo-2-chloro-3 -pyridyl)acetamide.HPLC-MS: (M-H) = 247.0; 249.0

According to the analysis of related databases, 169833-70-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; BALINT, Balazs; KOTSCHY, Andras; SIPOS, Melinda; WEBER, Csaba; FOLOPPE, Nicolas; WALMSLEY, David; BURBRIDGE, Michael, Frank; CRUZALEGUI, Francisco Humberto; (109 pag.)WO2017/55530; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72587-15-6, 2-Chloro-3-nitro-5-(trifluoromethyl)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, name: 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. name: 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Compound WXOO2-1 (295.68 mg, 662.13 tmol) and compound WXOO1-2 (354.9 mg, 1.30 nmol) weredissolved in acetonitrile (3.00 mE) at room temperature,followed by the addition of potassium carbonate (183.03mg, 1.32 mmol). The reaction mixture was heated at roomtemperature and stirred for 2 hours. After the reaction, themixture was diluted with water (10 mE) and extracted withethyl acetate (5 mEx2). The organic phases were combinedand dried over anhydrous sodium sulfate, followed byfiltration. The filtrate was concentrated under reduced pressure to remove the solvent. The obtained residue wasisolated by column chromatography (eluent: petroleumether/ethyl acetate=1 0/1-2/1, volume ratio) to obtain thetarget product WXOO2-2. MS-ESI mlz: 464.0 [M+H].

The synthetic route of 72587-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.; LUO, Yunfu; YANG, Chundao; LEI, Maoyi; LIU, LING; HU, Guoping; LI, Jian; CHEN, Shuhui; US2019/177318; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 40296-46-6 ,Some common heterocyclic compound, 40296-46-6, molecular formula is C8H7Cl2NO2, 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.

Sodium hydroxide (40 mL, 6.25 M solution) was added to a stirred solution of 4,6-dichloronicotinic acid ethyl ester (22) (25.95 g, 118 mmol) in 4:1:1 THF:MeOH:water (600 mL). After 30 minutes, the reaction mixture was acidified to pH 2 with concentrated HCl, diluted with 1:1 EtOAc:Et2O and washed with water and brine. The organic layer was dried (Na2SO4) and concentrated. The resulting off-white solid was twice concentrated from toluene to give the desired product (23) as a white solid (21.73 g, 96%).

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. 40296-46-6, Ethyl 4,6-dichloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wallace, Eli; Hurley, Brian; Yang, Hon Woon; Lyssikatos, Joseph; Blake, Jim; US2005/49419; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58584-86-4 , The common heterocyclic compound, 58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, 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 3-(dispiro[2.0.2. l]heptan-7-ylmethoxy)-lH-pyrazole (0.94 g, 4.9 mmol), ethyl 2,6-dichloropyridine-3-carboxylate (1.15 g, 5.23 mmol), potassium carbonate (0.83 g, 6.0 mmol), and l,4-diazabicyclo[2.2.2]octane (0.12 g, 1.1 mmol) in DMSO (16 mL) was stirred for 24 hours. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine and water, dried over sodium sulfate, and evaporated under vacuum. The residue was purified by silica gel column chromatography eluting with 0-20% ethyl acetate in hexanes to give ethyl 2-chloro-6-(3-(dispiro[2.0.2.1]heptan-7-ylmethoxy)-lH-pyrazol-l-yl)nicotinate (1.39 g, 75% yield) as a colorless solid. ESI-MS m/z calc. 373.11932, found 374.2 (M+l)+; Retention time: 0.87 minutes. *H NMR (400 MHz, Chloroform-d) delta 8.36 (d, J = 2.8 Hz, 1H), 8.27 (d, J = 8.5 Hz, 1H), 7.72 (d, J = 8.5 Hz, 1H), 5.96 (d, J = 2.9 Hz, 1H), 4.41 (q, J = 7.1 Hz, 2H), 4.30 (d, J = 7.0 Hz, 2H), 1.94 (t, J = 7.0 Hz, 1H), 1.42 (t, J = 7.1 Hz, 3H), 1.02-0.89 (m, 4H), 0.75-0.65 (m, 2H), 0.65-0.53 (m, 2H)

The synthetic route of 58584-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ALCACIO, Timothy; BAEK, Minson; GROOTENHUIS, Peter; HADIDA RUAH, Sara, Sabina; HUGHES, Robert, M.; KESHAVARZ-SHOKRI, Ali; MCAULEY-AOKI, Rachel; MCCARTNEY, Jason; MILLER, Mark, Thomas; VAN GOOR, Fredrick; ZHANG, Beili; ANDRESON, Corey; CLEVELAND, Thomas; FRIEMAN, Bryan, A.; KHATUYA, Haripada; JOSHI, Pramod, Virupax; KRENITSKY, Paul, John; MELILLO, Vito; PIERRE, Fabrice, Jean Denis; TERMIN, Andreas, P.; UY, Johnny; ZHOU, Jinglan; ABELA, Alexander, Russell; BUSCH, Brett, Bradley; PARASELLI, Prasuna; SIESEL, David, Andrew; (329 pag.)WO2018/64632; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1187236-18-5, 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 1187236-18-5 as follows.

Under the protection of -78 C and N2,To ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate (3.50 g, 13.0 mmol)Add in anhydrous DCM (80 mL) suspensionDiisobutylaluminum hydride (18.50 mL, 18.50 mmol, 1.0 M).The mixture was stirred at -78 C overnight.After the reaction is over, move to 0 C.And add water (0.75mL) in turn.15% NaOH aqueous solution (0.75mL)The reaction was quenched with water (2 mL).The resulting mixture was stirred at room temperature for 15 minutes.Then add Et2O (50 mL),EtOAc (50 mL) and Mg 2 SO 4 (20 g).Continue stirring for 15 minutes and filter again.The resulting filter cake was rinsed with EtOAc (200 mL).The filtrate was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc /EtOAcTo give the title compound as a pale yellow solid (1.50g, 51% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1187236-18-5, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
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. 1004294-58-9, name is 6-Bromo-5-chloropyridin-2-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-5-chloropyridin-2-amine

A solution of N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5-(2-chloro-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1 H-pyrazole-3-carboxamide (Preparation 7, 500 mg, 0.80 mmol), 6-bromo-5-chloropyridin-2-amine (332 mg, 1.60 mmol) and potassium carbonate (221 mg, 1.60 mmol) in dioxane (10 mL) and water (5 mL) was degassed with nitrogen for 10 minutes before the addition of Pd(PP i3)4 (92 mg, 0.80 mmol). The reaction was heated to reflux for 2 hours. The reaction was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (3 x 20 mL) and the combined organic layers were dried over MgS04 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 40- 60% EtOAc in heptanes and dissolved in THF (2 mL). TBAF (1 M in THF, 96 uL, 0.096 mmol) was added and the reaction stirred at room temperature for 18 hours. The reaction was quenched by the addition of saturated aqueous NH4CI solution (10 mL) and extracted into EtOAc (3 x 10 mL). The combined organic layers were dried over MgS04 and concentrated in vacuo. The residue was purified using reverse phase chromatography eluting with 5-50% MeCN in water with 0.1 % ammonia followed by trituration with MeCN to afford the title compound (8 mg, 8%). 1 H NMR (400MHz, DMSO-d6): delta ppm 3.31-3.35 (2H, m), 3.50 (2H, q), 4.75 (t, 2H), 6.33 (s, 2H), 6.50 (d, 1 H), 6.90 (s, 1 H), 7.45-7.49 (m, 1 H), 7.53-7.62 (m, 5H), 7.70-7.76 (m, 2H), 8.16 (t, 1 H), 10.79 (br s, 1 H). MS m/z 51 1 [M+H]+

The synthetic route of 1004294-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAGAL, Sharanjeet Kaur; CUI, Jingrong Jean; GREASLEY, Samantha Elizabeth; LUNNEY, Elizabeth Ann; MCALPINE, Indrawan James; NAGATA, Asako; NINKOVIC, Sacha; OMOTO, Kiyoyuki; SKERRATT, Sarah Elizabeth; STORER, Robert Ian; WARMUS, Joseph Scott; WO2015/159175; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application 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.

General procedure: A mixture of quinazolinone 19a or 19b-c (1.0 mmol) and NaH in DMF was maintained under N2 for 5 min. The appropriate haloderivative or aryloxirane was added (1.0mmol) andthe mixture was microwave irradiated at 120 C (power set point 250W; ramp time 30 sec; hold time 5 min). After cooling, the mixture was poured insat. NH4Cl solution (30 mL) and the obtained precipitate wascollected by filtration. The solid was purified by crystallization to give thetitle compounds.3-[(2?-Bromopyridin-3?-yl)methyl]-6,7-dimethoxyquinazolin-4(3H)-one (1). From 19a and 2-bromo-3-bromomethylpyridine:yield 26% (EtOAc); mp 282C;1H NMR (300 MHz, DMSO-d6): delta 8.43 (s, 1 H, 2-H); 8.32 (dd, J = 3.4 and 2.8 Hz, 1 H, 6?-H), 7.45 (s,1 H, 5-H or 10-H), 7.41-7.39 (m, 2 H, 4?-H and 5?-H), 7.20 (s, 1 H, 5-H or10-H), 5.19 (s, 2 H, NCH2), 3.93 (s, 3 H, OCH3), 3.86 (s,3 H, OCH3). 13CNMR (75 MHz, DMSO-d6): delta 159.39, 154.64, 149.02, 148.84, 146.65, 144.10,141.39, 137.22, 133.00, 123.60, 114.54, 107.99, 105.02, 55.99, 55.66, 48.75. Anal.calcd. for C16H14BrN3O3: C, 51.08;H, 3.75; Br, 21.24; N, 11.17; found: C, 51.10; H, 3.77; Br, 21.20; N, 11.19.HRMS (ESI-TOF) for C16H15BrN3O3 [M+ H]+: calcd.: 376.0291, found: 376.0296.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,94446-97-6, 2-Bromo-3-(bromomethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Article; Marzaro, Giovanni; Castagliuolo, Ignazio; Schirato, Giulia; Palu’, Giorgio; Dalla Via, Martina; Chilin, Adriana; Brun, Paola; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 416 – 425;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1211516-25-4, 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. 1211516-25-4, name is 6-Bromo-5-methylpicolinic acid. A new synthetic method of this compound is introduced below.

3-Chlorophenylboronic acid (CAN 63503-60-6, 0.61 g, 3.9 mmol), 1 , l’-bis(diphenyl- phosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464- 05-4, 53 mg, 0.065 mmol) and potassium carbonate (CAN 584-08-7, 0.54 g, 3.9 mmol) was added to a solution of 6-bromo-5-methyl-pyridine-2-carboxylic acid (0.7 g, 3.2 mmol) in water ( 30 mL). The mixture was stirred at 100°C overnight. The reaction mixture was adjusted to pH = 3 and the mixture was extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated in vacuo to give product (0.55 g, 56.9percent); MS (EI): m/e 248.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211516-25-4, 6-Bromo-5-methylpicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 104830-06-0, 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 104830-06-0, name is 2-Amino-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-Dimethylamino-1-(3-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-4-phenylcyclohexanol 2-Amino-3-iodopyridine (3,108 mg, 14.13 mmol), 4-(dimethylamino)-4-phenyl-1-(prop-1-ynyl)cyclohexanol (4,000 mg, 15.54 mmol), lithium chloride (630 mg, 14.83 mmol) and sodium carbonate (4.49 g, 42.38 mmol) were combined in dimethylformamide (absolute, 60 ml) in an argon atmosphere. The catalyst ([Pd(dppf)Cl2*CH2Cl2], 1,154 mg, 1.41 mmol) was then added. The red solution was heated at 79 C. (oil bath temperature) for 5 h. To bring the reaction to completion, a further 0.3 equivalent of 2-amino-3-iodopyridine (932 mg, 4.24 mmol) and 0.05 equivalent of catalyst (577 mg, 0.71 mmol) were added. Thereafter, the mixture was stirred at 99 C. (oil bath temperature) for a further 2 h. The black reaction mixture was cooled to room temperature and water (50 ml; stirring for 10 min) and methylene chloride (50 ml) were added in succession. The phases were separated (the mixture was filtered over kieselguhr) and the aqueous phase was extracted with methylene chloride (3*20 ml). The combined organic phases were washed with saturated NaCl solution (3*20 ml) and dried over sodium sulfate. After filtration, the volatile constituents were removed completely in vacuo. The residue was absorbed on kieselguhr and separated by chromatography (silica gel [200 g]; chloroform/ethanol [9:1 1,000 ml]). 1,200 mg (3.43 mmol; 22% of the non-polar diastereomer were isolated as a colourless solid.

According to the analysis of related databases, 104830-06-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUNENTHAL GmbH; US2010/9986; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-89-9, 2,3-Dibromopyridine, 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, Formula: C5H3Br2N, blongs to pyridine-derivatives compound. Formula: C5H3Br2N

General procedure: 2,4-Dibromopyridine (0.236 g, 1 mmol) and phenol (0.094 g, 1 mmol), CuI (19.0 mg, 0.1 mmol), TMEDA (11.6 mg, 0.1 mmol), and cesium carbonate (0.65 g, 2 mmol) were placed in DMSO (5 mL). The reaction was stirred at 110 C under nitrogen atmosphere for 24 h. When the reaction mixture was cooled, the reaction mixture was filtered. The mixture was dissolved with dichloromethane (25 mL). Then the mixture was washed with brine (3×30 mL). The organic phase was dried over sodium sulfate. After evaporation of the solvent, the mixture was subjected to column chromatography with petroleum ether/ethyl acetate (20:1) as eluent to give pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-89-9, 2,3-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Qizhong; Zhang, Bin; Du, Tieqi; Gu, Haining; Ye, Yuyuan; Jiang, Huajiang; Chen, Rener; Tetrahedron; vol. 69; 1; (2013); p. 327 – 333;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem