Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 14916-63-3, 6-Nitropyridin-2-amine, 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, 14916-63-3, blongs to pyridine-derivatives compound. Computed Properties of C5H5N3O2

Copper (II) chloride (5.8 g) and t-butylnitrite (6.1 ml) were stirred in THF (150 ml) under argon and heated to 65 C. 2-Amino-6-nitropyridine (Shurko, O. P., Mamaev, V. P., Chem Heterocycl Comp, 26, 1990,1 47-52; 5 g, 36 mmol) was added portionwise. The reaction was stirred at 65 C. for 1 hour then allowed to cool to room temperature. EtOAc (200 ml) was added and the organic layer was washed with 2M HCl, water and dried. Volatile material was removed by evaporation to give a sticky orange solid which was triturated with hexane to give the title compound (3.4 g) as a brown/orange solid. NMR: 7.8 (d, 1H), 8.6 (d, 1H), 9.2 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14916-63-3, its application will become more common.

Reference:
Patent; AstraZeneca AB; US6689909; (2004); B1;,
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. 914349-75-0, name is 5-(4-Fluorophenyl)picolinonitrile, molecular formula is C12H7FN2, 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. SDS of cas: 914349-75-0

5-(4-fluorophenyl)picolinonitrile (1.5 g) was dissolved in dry THF (20 mL) and cooled in an ethanol / CO2 bath. 1 M LiAlH4 in THF (20 mL) was added and the mixture stirred at below room temperature for 2 h. The reaction was quenched by the dropwise addition of 1 : 10 water : THF (20 mL), diluted with ethyl acetate, stirred with 1 M NaOH and the organic phase decanted, washed with 1 M NaOH, brine and dried. Evaporation gave the title compound as an amorphous yellow solid, used immediately and without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 914349-75-0.

Reference:
Article; Greig, Iain R.; Baillie, Gemma L.; Abdelrahman, Mostafa; Trembleau, Laurent; Ross, Ruth A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 18; (2016); p. 4403 – 4407;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256808-59-9 , The common heterocyclic compound, 1256808-59-9, name is 5-Fluoro-3-methylpicolinic acid, molecular formula is C7H6FNO2, 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 tert-butyl ((3aS,4R,8R)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39AB, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-fluoro-3-methylpicolinic acid (82 mg, 0.53 mmol) followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by column chromatography (silica gel, eluting with petroleum ether / ethyl acetate 1: 1) to yield, after drying in vacuo, the title compound as a yellow solid (130 mg, 66% yield). XH NMR (CDC13, 400 MHz): delta 1.50-1.59 (m, 1 H), 1.66 (s, 9 H), 1.86 (s, 3 H), 1.97 (s, 3 H), 2.06-2.12 (m, 1 H), 2.14 (s, 3 H), 2.84 (s, 3 H), 3.54 (dd, J = 7.7, 10.7 Hz, 1 H), 3.69 (ddd, J = 4.8, 10.7, 10.7 Hz, 1 H), 4.30 (ddd, / = 2.1, 7.1, 12.0 Hz, 1 H), 7.40 (dd, J = 2.1, 8.9 Hz, 1 H), 7.58 (dd, = 9.1, 10.0 Hz, 1 H), 8.31 (d, J = 2.6 Hz, 1 H), 8.49 (dd, / = 3.1, 8.9 Hz, 1 H), 10.78 (s, 1 H), 12.54 (s, 1 H). MS (ES+) m/z 563.2 [M+H].

The synthetic route of 1256808-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 87674-15-5, 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. 87674-15-5, name is 1-(3-Fluoropyridin-4-yl)ethanol, molecular formula is C7H8FNO, 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.

A mixture of 1-(3-fluoropyridin-4-yl)ethanol (10 g, 70.3 mmol) and commercial activated MnO2 (8 g, 92.1 mmol) in toluene (100 mL) were refluxed until disappearance of starting material. After cooling, the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3-fluoro-4-acetyl pyridine (6.9 g, 70%) that was used directly in the next step.

According to the analysis of related databases, 87674-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142415; (2007); 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. 72093-04-0, name is 3-Chloro-4-methylpyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 72093-04-0

To a solution of lithium diisopropylamide (6mL, 2M in THF, l2mmol) in 5mL THF at -70C was added under argon a solution of 3-chloro-4-methylpyridine (1 .28g, leq, 1 Ommol) in 5mL THF. The mixture was stirred for 5mm at -70C and then allowed to reach -3 0C. Thereafter the mixture was cooled down to – 70C and a solution of 1-chloro-3,3-dimethylbutan-2-one (2.7g. 2eq, 2Ommol) in 5mL THF was added. Then the mixture was allowed to reach ambient temperature and stirred for lh. Thereafter the mixture wascooled to 0C and saturated aqueous ammonium chloride solution was added. After extraction with ethyl acetate and evaporation of the solvent the cmde material was purified via column chromatography over silica gel (eluent cyclohexane ethyl acetate gradient). After evaporation of the solvent 2g (8 1%) of 4-[(2- tert-butyloxiran-2-yl)methyl]-3-chloropyridine were obtained as colourless oil.MS (ESI): 226.1 ([M+H]+)

The synthetic route of 72093-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; HOFFMANN, Sebastian; SUDAU, Alexander; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; BERNIER, David; BRUNET, Stephane; LACHAISE, Helene; VIDAL, Jacky; GENIX, Pierre; COQUERON, Pierre-Yves; GEIST, Julie; VORS, Jean-Pierre; KENNEL, Philippe; MILLER, Ricarda; WO2014/167010; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90395-45-2 ,Some common heterocyclic compound, 90395-45-2, molecular formula is C13H11NO, 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.

1-(4-Pyridin-3-ylphenyl)-ethanone (33 g, 166.8 mmole),3,5-Dibromo-benzaldehyde (42.06 g, 159.34 mmole), and 840 ml of ethanol were added to the reaction flask for stirring.Finally, sodium tert-butoxide (22.94 g, 239 mmole) was added and stirred at room temperature.After the reaction has been completed, 200 ml of deionized water is added and stirred for filtration. The solid is filtered and washed with deionized water and methanol. The solid is then filtered with 100 ml of deionized water and 200 ml of methanol for 30 minutes, and repeated twice. Dry the solid to give 55 g of pale yellow solid 3-(3,5-dibromophenyl)-1-(4-pyridin-3-ylphenyl)-acetone(3-(3,5-Dibromo-phenyl)-1-(4-pyridin-3-yl-phenyl)-propanone),The yield was 77.89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90395-45-2, its application will become more common.

Reference:
Patent; E-ray Optoelectronics Technology Co Ltd; Huang, Heh Lung; Guo, Huang Ming; Chao, Teng Chih; Lin, Chi Jen; Chang, Min Jong; (53 pag.)TW2019/30287; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256785-86-0, 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.1256785-86-0, name is 1-(4-Aminopyridin-2-yl)ethanone, molecular formula is C7H8N2O, molecular weight is 136.15, as common compound, the synthetic route is as follows.

Example 20 (2R,5S)-N-(2-Acetyl-4-pyridyl)-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carboxamide While stirring with ice-cooling, 12.5 ml of trifluoroacetic acid was added to 12.5 ml of chloroform solution containing 1.41 g of 2-acetyl-4-pyridinylcarbamic acid t-butyl ester.. The mixture was immediately warmed up to room temperature and stirred for 2 hours and 40 minutes.. The solvent was evaporated under reduced pressure to obtain a crude amine.. This compound was dissolved in 25 ml of pyridine, and the solution was mixed with 0.83 ml of phenyl chloroformate while stirring with ice-cooling and then immediately warmed up to room temperature.. After 8 hours and 30 minutes, this was mixed with 10 ml of pyridine solution containing 1.4 g of (2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile and heated under reflux for 1 hour.. The reaction mixture cooled to room temperature was mixed with water and extracted with chloroform.. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure.. The residue was purified by a silica gel column chromatography to obtain 1.03 g of the title compound from methanol-chloroform (1:99, v/v) elude. NMR: 1.10 (3H, d, J=7), 1.20 (3H, d, J=7), 2.61 (3H, s), 3.34-3.52 (2H, m), 3.75 (1H, d, J=14), 3.92 (1H, d, J=14), 4.28-4.45 (1H, m), 4.46-4.62 (I H, m), 7.20-7.35 (2H, m), 7.78-7.91 (2H, m), 8.12 (1H, d, J=2), 8.48 (1H, d, J=6), 9.24(1H, s)

The chemical industry reduces the impact on the environment during synthesis 1256785-86-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co. Ltd.; US6673799; (2004); B1;,
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.72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

240 mg (1.19 mmol) of 2-chloro-5-(trifluoromethyl)pyridin-3-amine and 357 mg (1.31 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid were dissolved together with 0.39 ml (4.78 mmol) of pyridine in 20 ml of dioxane, 367 mg (2.39 mmol) of phosphoryl chloride were added, and the mixture was stirred at reflux for 90 min. The mixture was concentrated, the residue was taken up in ethyl acetate and washed with water, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography purification with a cyclohexane/ethyl acetate gradient (80:20 to 40:60) as eluent. (log P (neutral): 5.71; MH+: 412; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 1.37 (t, 3H), 3.12 (q, 2H), 7.74-7.84 (m, 2H), 8.07-8.14 (m, 2H), 8.49 (s, 1H), 8.70 (s, 1H), 9.02 (s, 1H), 11.12 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; HAGER, Dominik; HOFFMEISTER, Laura; KAUSCH-BUSIES, Nina; WILCKE, David; WILLOT, Matthieu; GOeRGENS, Urich; ILG, Kerstin; MOSRIN, Marc; PORTZ, Daniela; TURBERG, Andreas; US2018/305353; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0 ,Some common heterocyclic compound, 628691-93-0, molecular formula is C6H3ClFNO2, 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.

Carbonyldiimidazole (1.80 g, 1 1.1 mmol) was added to a solution of 2-chloro-3-fluoro- isonicotinic acid (1.3 g, 7.41 mmol) in THF (21.2 mL). The reaction mixture was stirred at RT overnight and was then added to a cold (0C) solution of NaBH4 (1.40 g, 37 mmol) in water (52.9 mL). The mixture was stirred for 10 min at 0C, and 1 M HCI was then added carefully to quench the reaction (caution: H2 evolving). Volatiles were removed via rotary evaporation and the residue was dissolved in saturated aqueous NaHC03. The mixture was extracted repeatedly with CH2CI2, the combined organics were dried (phase separator) and concentrated in vaccuo. Purification by flash column chromatography on silica gel (eluent gradient: c- hexane/EtOAc 4: 1 to 2: 1) afforded the title compound as a white solid. TLC, Rf (c- hexane/EtOAc 1 :1) = 0.37; MS (LC/MS): 162.0 [M+H]+; tR (HPLC conditions b): 1.60 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,628691-93-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; SIMIC, Oliver; VULPETTI, Anna; ROGEL, Olivier; WO2012/93101; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156072-84-3, Adding some certain compound to certain chemical reactions, such as: 156072-84-3, name is 5-Chloro-2-cyano-3-methylpyridine,molecular formula is C7H5ClN2, 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 156072-84-3.

Step 2: Synthesis of 5-chloro-3-methylpicolinic acid To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH 5.0N (110 ml, 550 mmol). The resulting mixture was refluxed at 90 C. for 18 h. After cooling to RT, the reaction mixture was concentrated, diluted with water and the pH of the solution was adjusted to 4 by addition of 5N HCl. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2*). The aqueous layer was again acidified with 5N HCl to pH 4 and extracted with EtOAc (2*). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C. for 12 h to give the title compound 5-chloro-3-methylpicolinic acid (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z=172.0 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.29 (br. s., 1H), 8.41 (d, J=1.76 Hz, 1H), 7.73 (d, J=1.76 Hz, 1H), 2.75 (s, 3H).

According to the analysis of related databases, 156072-84-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem