Category: pyridine-derivatives

Reference of 960289-03-6, 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.960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, molecular formula is C7H6BrNOS, molecular weight is 232.1, as common compound, the synthetic route is as follows.

Preparation 22; 2-(4-Fluoro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridine-7-one; Add tetrakis(triphenylphosphine) palladium(O) (0.075g, 0.065 mmol) to a degassed solution of 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.5 g, 2.15 mmol), 4-fluorophenylboronic acid (0.30 g, 2.15 mmol), and sodium carbonate (0.46 g, 4.30 mmol) in N,N-dimethylformamide (21 mL), methanol (5 mL) and water (1 mL). Heat the reaction at 90 0C for 16 h. Allow the reaction to cool to RT and pour into water (75 mL). Filter the resulting solid and dry in vacuo at 80 0C to give 0.40 g (75%) of the title compound. MS/ES m/z 248.0 [M+H]+ .

The chemical industry reduces the impact on the environment during synthesis 960289-03-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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. 89415-54-3, name is 5-Bromo-N2-methylpyridine-2,3-diamine, the common compound, a new synthetic route is introduced below. Formula: C6H8BrN3

A solution of 5-bromo-N*2*-methylpyridine-2,3-diamine (Stage 67.1.4, 960 mg, 4 75 mmo.) and tetramethyl orthocarbonate (Aki?ch, Buchs, Switzerland, 2 ml, 14 7 mmol) and acetic acid (0 273 ml, 4 75 mmol) was stirred for 90 min at 100 C The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine The aqueous layer was extracted with EtOAc and the combined organic layers washed with saturated aqueous NaHCO3 and with brine, then dried over Na2SO4, filtered and evaprated The crude product was dry loaded on silica gel and purifted by MPLC (DCM/MeOH 0% – 4%) to g>;ve the title compound as a green solid. (HPLC tR 2.83 mm (Method A), M+H – 242, 244 MS-ES).

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63237-88-7, 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Preparation 99Methyl 6- r(1 RV1 -(4-fluorophenvnethyll(pyrazolori ,5-alpyridin-2- ylcarbonyl)amino}methyl)pyridine-2-carboxylate To a stirred solution of the amine from Preparation 20 (49mg, 0.17mmol) in dichloromethane (1 ml_) was added pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (27.6mg, 0.17mmol) followed by N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (32.6mg, 0.17mmol) and the reaction mixture was stirred for 23 hours. Saturated aqueous NaHC03 solution (2ml_) was added and the mixture was stirred vigorously for 10 minutes before filtering through a phase separation cartridge. The solvent was removed in vacuo and the residue purified by column chromatography (silica 50-100% ethyl acetate in pentane as eluent). The solvent was removed in vacuo to give the title compound as a clear gum (37mg, 50%). 1 H NMR (400 MHz, CDCI3): the compound appears to exist as two non-interconverting rotameric forms in CDCI3 in the ratio ca. 2:1. Data for these rotamers are listed separately.Major: delta ppm: 1.62 (d, 3H), 3.99 (s, 3H), 4.56 (d, 1 H), 4.94 (d, 1 H), 6.21 -6.35 (m, 1 H), 6.82-6.99 (m, 4H), 7.17 (t, 1 H), 7.28-7.39 (m, 2H), 7.50 (d, 1 H), 7.59 (d, 1 H), 7.70 (t, 1 H), 7.92 (d, 1 H), 8.47 (d, 1 H).Minor: delta ppm: 1.56 (d, 3H), 3.99 (s, 3H), 5.05 (d, 1 H), 5.31 (d, 1 H), 6.21 -6.35 (m, 1 H), 6.72 (t, 1 H), 6.82-6.99 (m, 3H), 7.08 (t, 1 H), 7.28-7.39 (m, 3H), 7.50 (d, 1 H), 7.58 (d, 1 H), 7.86 (d, 1 H), 8.16 (d, 1 H).LRMS (ESI) m/z 433 [MH]+

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; GLOSSOP, Paul Alan; PALMER, Michael John; ANDREWS, Mark David; WO2012/120398; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 188577-69-7, name is 3,4-Dichloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 188577-69-7

3,4-dichloro-2-aminopyridine (500 mg, 3.07 mmol, prepared with reference to document: Synthetic Communications, 1997, 27(5), 861-870.) and 2-fluoro-4-nitrophenol (1.928 g, 12.27 mmol) were heated to 120 C. and melted, and stirred for 24 hrs. The molten was cooled to room temperature, and subjected to silica gel column chromatography (the eluent was dichloromethane to dichloromethane/methanol=50/1) for purification, to obtain a white solid (137 mg, 16%). 1H NMR (DMSO-d6, 300 MHz) delta 8.38 (dd, 1H, J=10.5, 2.4 Hz), 8.148.09 (m, 1H), 7.86 (d, 1H, J=5.4 Hz), 7.427.36 (m, 1H), 6.60 (br, 2H), 6.27 (d, 1H, J=5.4 Hz).

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, 188577-69-7, 3,4-Dichloropyridin-2-amine.

Reference:
Patent; SHANGHAI HUILUN LIFE SCIENCE & TECHNOLOGY CO., LTD; Cheng, Jianjun; Qin, Jihong; Ye, Bin; US2014/206679; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109306-86-7 , The common heterocyclic compound, 109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, 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.

2- (2-bromophenyl) pyridine(40.7 g, 174.0 mmol) was dissolved in 500 ml of anhydrous THF and cooled to -78 C. 2.5 M n-BuLi (73.2 ml, 183 mmol) was slowly added thereto and stirred for 1 hour.To this reaction solution was added 9-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] dioxin-11-one (53.0 g, 165.4 mmol) obtained in the above Step 3 The temperature was then slowly raised to room temperature and stirred for 3 hours.Aqueous ammonium chloride solution was added to terminate the reaction, distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure and then purified by column chromatography to obtain the compound 9-chloro-11- (2- (pyridin-2-yl) phenyl) -11H-indeno [ Benzo [b, e] [1,4] dioxin-11-ol (69.6 g, yield 80%).

The synthetic route of 109306-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doosan Co., Ltd; Choi Tae-jin; Kim Yeong-bae; Kim Hoe-mun; (65 pag.)KR2019/30391; (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. 124870-33-3, name is Methyl 2-(3-cyanopyridin-4-yl)acetate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C9H8N2O2

1.58g of (3-cyano-pyridine-4-yl) -acetic acid methyl ester was dissolved in 18 mL of ethanol and slowly added with 682mg of sodium borohydride at-0 C and stirred for about 2 hours. The above mixture was added with 3 mL of saturated solution of ammonium chloride, diluted with 200 mL ethylacetate. Then, the organic solvent layer was washed with water, and saturated solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. The filtrate was concentreated under reduced pressure and a silica gel column chromatography was performed on the resulting residue by using a mixed eluant of methylene chloride and methanol, wherein methylene chloride and methanol are mixed in 50: 1 volume ratio, and 1.02g (74%) of 4- (2-hydroxy-ethyl)-nicotinonitrile was obtained in colorless oil. 1H NMR (300 MHz, CDCI3) 8 8. 82 (s, 1H), 8.69 (d, 1H, J=5. 4Hz), 7.39 (d, 1H, J=5. 4Hz), 3.99 (t, 2H, J=6. 3Hz), 3.10 (t, 2H, J=6. 3Hz).

The synthetic route of 124870-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK CHEMICALS, CO., LTD.; WO2005/63768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1401624-81-4, 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 1401624-81-4 as follows.

A solution of 2,6-dlbromo-[1 ,2,4]trlazolo[i,5-a]pyrldlne (2.7 g, 9.7 mmol), triethylamlne (2.94 g, 29.1 mmol), and N-methylpiperazlne (1.94 g, 19.4 mmol) in toluene was refluxed overnight. The solvent was removed under vacuum, and the residue was purified by HPFC (PE: EA -1 : 1) to yield PZ972-3 (1.82 g, 63%). LC-MS: 296.1, 298.1 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1401624-81-4, its application will become more common.

Reference:
Patent; PROZYMEX A/S; PEDERSEN, John; LAURITZEN, Conni; WO2012/130299; (2012); 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. 83393-46-8, name is 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone. A new synthetic method of this compound is introduced below., Formula: C9H8N2O

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

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, 83393-46-8, 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
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. 54718-39-7, name is 2,5,6-Trichloronicotinic acid. A new synthetic method of this compound is introduced below., SDS of cas: 54718-39-7

1,1 ?-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6- trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif.) in THF (400 mE), allowing gas evolution to cease between addition. The resulting mixture was stirred for 5 mm and then was degassed with house vacuum and flushed with nitrogen. The resulting mixture was heated to 50 C. for 60 mm, then diluted with toluene (100 mE) and concentrated to half the initial volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mE, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 mm at it, diluted with EtOAc (200 mE) and washed with water (3×100 mE). The organic layer was dried over anhydrous Na2504 and concentrated in vacuo. The residue was suspended in 9:1 heptane/EtOAc (300 mE) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half the initial volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloroni- cotinamide.

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, 54718-39-7, 2,5,6-Trichloronicotinic acid.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; BOOKER, Shon; GOODMAN, Clifford; REED, Anthony B.; LOW, Jonathan D.; WANG, Hui-Ling; CHEN, Ning; MINATTI, Ana Elena; WURZ, Ryan; CEE, Victor J.; (88 pag.)US2019/77801; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 851607-27-7, 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 851607-27-7 as follows.

[1037] To a stirred mixture of compound 3 (4 g, 18.1 mmol), compound 4 (4.52 g 21.72 mmol), and K2CO3 (5 g, 36.2 mmol) in DME/H2O (48 mL, v/v=5/1) was added Pd(dppf)Cl2 (668 mg, 0.91 mmol) under N2 protection. The reaction mixture was degassed with nitrogen again and refluxed overnight. The mixture was concentrated, diluted with H2O and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (PE/EA=2/1) to give compound 5 (2.8 g, 69% yield) as a pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851607-27-7, its application will become more common.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem