Day: June 4, 2021

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 126053-15-4, name is 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

Example A4PXQP ar ation _o_ f intermediate 14 ; Dibromotriphenyl- phosphorane (0.004 mol) was added to a solution of 4-chloro-6,7- dihydro- 5H-Cyclopenta[b]pyridin-7-ol (0.002 mol) in acetonitrile (6 ml). The mixture was stirred for 3 hours, quenched with potassium carbonate 10% and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (1.6g) was purified by column chromatography over silica gel (15-40 mum) (eluent DCM 100). The pure fractions were collected and the solvent was evaporated till dryness, yielding 0.3 Ig (67%) of intermediate 14.

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, 126053-15-4, 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/118384; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 100367-39-3, 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. 100367-39-3, name is 4-Bromo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

A suspension of 4-bromo-2-methoxypyridine (1.225 g, 6.511 mmol), A- methylthiophenyl boronic acid (2.188 g, 13.02 mmol), PdCl2(dppf) (531 mg, 0.651 mmol) Attorney’s Docket 2882.023B and K2CO3 (1.797 g, 13.02 mmol) in DMSO (10 niL) was degassed under reduced pressure for 25 min. The suspension was put under N2 and stirred at 95 0C for 16 h. The suspension was cooled, H2O was added, and the suspension was filtered to afford a light colored solid. Flash chromatography (silica gel, hexanes/(l :l EtOAc/hexanes), 100:0 to 0 : 100) afforded 1.10 g of a white powder

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100367-39-3, 4-Bromo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100137-47-1 ,Some common heterocyclic compound, 100137-47-1, molecular formula is C6H7N3O, 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 4-aminopyridine-2-carboxamide (2.559 g, 18.66 mmol) and diisopropylethylamine (6.03 g, 46.65 mmol) in dichloromethane (28.5 mL) cooled at 0C was added dropwise a solution of 6-bromo- 2- fluoro-3-(trifluoromethyl)benzoyl chloride (5.7 g, 18.66 mmol) in dichloromethane (28.5 mL). The mixture was stirred at room temperature overnight. Ethyl acetate (150ml) was added to the mixture was washed with water. The organic layer was dried over sodium sulfate and concentrated. Purification by silica gel chromatography (dichloromethane/methanol gradient) gave 4-[[6-bromo-2-fluoro-3- (trifluoromethyl)benzoyl]amino]pyridine-2-carboxamide (800 mg, 11%). ESI-MS m/z calc. 406.97, found 408.2 (M+l)+; retention time (Method A): 0.58 minutes (1.2 minute run).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100137-47-1, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5345-47-1, 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. 5345-47-1, name is 2-Aminonicotinic acid, molecular formula is C6H6N2O2, 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.

EXAMPLE 1 2-Amino-5-bromo-3-pyridine Carboxylic Acid To a solution of 2-amino-nicotinic acid (10 g, 72.5 mmol) in acetic acid (70 mL) was dropwise added bromine (9.8 mL, 79.8 mmol) at room temperature under nitrogen. Upon completion of the reaction, the solvent was removed in vacuo, the residue triturated with ether and collected on a filter to give 2-amino-5-bromo-3-pyridine carboxylic acid as a yellow solid (15.7 g, 99%): mp 272 C., (decomposed); 1H-NMR (DMSO-d6) delta 8.8-7.8 (bs, 2H), 8.44 (d, 1H, J=2.48 Hz), 8.34 (d, 1H, J=2.48 Hz); MS (EI) m/z 216/218 ([M+H]+, 100%).

According to the analysis of related databases, 5345-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6399593; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 133627-45-9, 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 133627-45-9, name is 2-Chloro-4-methylpyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-chloro-4-methylpyridin-3-amine [133627-45-9] (3.0 g, 21.0 mmol) in acetic acid (300 mL) was treated with a solution of sodium nitrite (1.45 g, 21.0 mmol) in water (2.5 mL). The reaction mixture was stirred at RT for 24 h. An additional solution of sodium nitrite (500 mg, 7.25 mmol) in water (1 mL) was added to the mixture which was allowed to stir at RT for 3h. Acetic acid was evaporated under reduced pressure and the residual aq. solution was partitioned between EtOAc and sat. aq. NaHCO3. The solid was filtered and dried under vacuum to yield batch 1 of product. The organic filtrate was washed with water and brine, then dried (phase separator) and concentrated to afford batch 2. The two batches were combined to give 7-chloro-iH-pyrazolo[3,4-c]pyridine as a solid. MS (LC/MS): 153 [M+H]+, tR (HPLC conditions d): 0.9 mm.

According to the analysis of related databases, 133627-45-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; VULPETTI, Anna; FLOHR, Stefanie; WO2014/2058; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14150-94-8, 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 14150-94-8 as follows.

To a solution of 1-methyl-3,5-dinitro-2-pyridone (8.0 g, 40 mmol) in methyl alcohol (20 mL) was added dropwise 3-methyl-2-butanone (5.1 mL, 48 mmol), followed by ammonia solution in methyl alcohol (10.0 g, 17%, 100 mmol). The reaction mixture was heated at 70 C. for 2.5 h under atmospheric pressure. The solvent was removed under vacuum and the residual oil was dissolved in CH2Cl2, and then filtered. The filtrate was dried over Na2SO4 and concentrated to afford 2-isopropyl-5-nitro-pyridine (1.88 g, 28%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14150-94-8, its application will become more common.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1204296-03-6, 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.1204296-03-6, name is 2-Chloro-4-(difluoromethyl)pyridine, molecular formula is C6H4ClF2N, molecular weight is 163.55, as common compound, the synthetic route is as follows.

Palladium acetate (275 mg, 1.22 mmol, 0.05 eq.) and 2-dicyclohexylphosphino- 2′,4′,6′-triisopropylbiphenyl (Sigma-Aldrich, product number 638064, 1.17 g, 2.45 mmol, 0.10 eq.) are dissolved in 1,4-dioxane (10 mL) under nitrogen atmosphere, and the resulting mixture is allowed to stir at room temperature for 45 minutes. This solution is then added to a mixture of tert-butylcarbamate (Sigma, product number 167398, 4.30 g, 36.7 mmol, 1.5 eq.), CS2CO3(15.9 g, 48.8 mmol, 2.0 eq.) and 2-chloro-4-difluoromethyl-pyridine (Manchester Organics, product number U15343, 4.00 g, 24.5 mmol, 1.0 eq.) in 1,4-dioxane (80 mL) under nitrogen atmosphere. The resulting reaction mixture is then heated at 90 C for 3 hours, during which it turned brownish. After this time, the mixture is allowed to cool to room temperature. It is then diluted with ethyl acetate, washed with an aqueous saturated solution of ammonium chloride (2 x 30 mL) and deionized water. The organic layer is dried over anhydrous sodium sulfate, filtered and the solvent is evaporated under reduced pressure. The brownish residue is mixed with 4 M HC1 in dioxane (50 mL, excess) and methanol (20 mL), and then heated at 80 C for 45 minutes. Deionized water is added and the aqueous layer is washed with ethyl acetate (3 x). The aqueous layer is then basified to pH = 9, with solid sodium hydroxide. The aqueous layer is extracted with ethyl acetate (3 x). The combined organic layer is dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure. The desired product i65 is obtained as a colorless solid, which is used in the next step without further purification (98% yield). 1H NMR (400 MHz, CDC13): 5 8.16 (d,2JH,H= 5.2 Uz, 1 H), 6.74 (d, 4.8 Hz, 1 H), 6.59 (s, 1 H), 6.51 (t,2JH,F= 56 Hz, 1 H), 4.61 (br s, 2 H);19F NMR (376 MHz, CDC13): delta – 116.0 (s, 2 F).

The chemical industry reduces the impact on the environment during synthesis 1204296-03-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PIQUR THERAPEUTICS AG; THE TRUSTEES OF THE UNIVERSITY OF PENNESYLVANIA; FABBRO, Doriano; HEBEISEN, Paul; HILLMANN-WUELLNER, Petra; STUETZ, Anton; SEYKORA, John, T.; BEAUFILS, Florent; (182 pag.)WO2017/198347; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6602-32-0 ,Some common heterocyclic compound, 6602-32-0, molecular formula is C5H4BrNO, 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.

Diisopropyl azodicarboxylate (4.65 mL, 24 mmol) was added slowly to a dioxane(200 mL) solution of 2-bromo-pyridin-3-ol (3.50 g, 20 mmol), 3-aminopropanol (1.67 mL, 22 mmol) and triphenylphosphine (6.30 g, 24 mmol) at 10 0C. After stirring the mixture for 30 min at this temperature, it was refluxed for 18 h Upon cooling, the volatiles were evaporated and the residue was purified by chromatography (silica, 3% MeOH in CH2Cl2 then 5% (2M NH3 in MeOH) in CH2Cl2 to afford the title compound (3.19 g, 69%). 1U NMR (300 MHz, CDCl3, delta): 7.98 (dd, J =4.5, 1.8 Hz, IH), 7.23 (dd, J =4.5, 8.2 Hz, IH), 7.15 (dd, J =I .8, 8.2 Hz, IH), 4.15 (t, J =6.0 Hz, 2H), 2.98 (t, J =6.6 Hz, 2H), 2.00 (m, 2H). MS (ESI): m/e 231 and 233 (M+H)+.

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. 6602-32-0, 2-Bromo-3-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2008/9122; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-30-3, 3-Bromo-5-nitropyridine, 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, 15862-30-3, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-5-nitropyridine

Preparation of Compound 68B: (0490) To a 25 mL flask was added (E)-tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate (200 mg, 706 mumol), 3-bromo-5-nitropyridine (143 mg, 706 mumol), K2CO3 (293 mg, 2.12 mmol), dimethyl ether (4 mL), water (0.5 mL) and Pd(Ph3P)4 (81.6 mg, 70.6 mumol). Then the mixture was degassed for five times and was heated to 85 C. (oil bath) for 23 hours. The mixture was diluted with EA and water, filtered through celite. The organic layer was separated and the aqueous layer was extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give a brown oil. After purification via combifalsh (eluted with EA/PE=035%), about 160 mg (E)-tert-butyl (3-(5-nitropyridin-3-yl)allyl)carbamate (Compound 68B) was obtained as yellow sticky solid. MS: calc’d 280 (M+H)+, measured 280 (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,15862-30-3, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; Hoves, Sabine; Wang, Lisha; Yun, Hongying; Zhang, Weixing; Zhu, Wei; (58 pag.)US2016/257653; (2016); A1;,
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.55676-22-7, name is 3-Acetyl-6-chloropyridine, molecular formula is C7H6ClNO, molecular weight is 155.5816, as common compound, the synthetic route is as follows.Product Details of 55676-22-7

To a 500 ml flask was added 6-chloro-3-acetylpyridine (18.7 g, 0.12 mol)P-cresol (14.26 g, 0.132 mol) and cesium carbonate (39 g, 0.12 mol)And DMF (300 ml) solvent.Heating reflux,After 1h, stop heating and cooling. The reaction solution was poured into excess water, stirred to precipitate a solid,filter. The crude product was recrystallized from ethyl acetate. Dried, weighed 16g, light yellow crystals, the yield was 58.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55676-22-7, 3-Acetyl-6-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; China Agricultural University; Tan Zhaohai; Yang Dongyan; (19 pag.)CN106946770; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem