Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]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, 10592-27-5, blongs to pyridine-derivatives compound. Application In Synthesis of 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

A solution OF BR2 (18.1 ML, 56.2 g, 0. 351 mol) in dry CH2CL2 (250 mL) was added dropwise over a period of 1 h 45 min to a stirred and cooled (-5 C) solution of 2 (42. 22 g, 0.351 mol) in dry CH2CL2 (410 ML)-PYRIDINE (40 mL). The yellow suspension WAS STIRRED AT 0 C for 45 min and poured into A mixture of saturated aqueous NaHCO3 (800 ML) and saturated aqueous NA2S203 (100 mL). Methanol (10 ML) was added and the lower organic layer was separated and dried over MGS04. The aqueous layer was extracted with AcOEt: MEOH=99 : 1 (7×1000 mL). These extracts were also dried with MgSO4. The organic solutions were combined and concentrated to afford 5 (59. 17 g, 85%), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) No. 3. 07 (tt, J = 8.4, 1.1 Hz, 2H), 3.64 (T, J = 8. 4 Hz, 2H), 4.47 (bs, 1H), 7.31 (m, 1H), 7. 85 (dt, J= 2.1, 0.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10592-27-5, its application will become more common.

Reference:
Patent; EISAI LONDON RESEARCH LABORATORIES LIMITED; WO2004/78757; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 109-04-6, 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. 109-04-6, name is 2-Bromopyridine. A new synthetic method of this compound is introduced below.

General procedure: A mixture of magnesium turnings (0.036g, 1.5mmol), bromobenzene (0.15g, 1mmol), tri-n-butyltin chloride (0.49g, 1.5mmol) and 1,2-dibromoethane (0.094g, 0.5mmol) as initiator in dry THF (5mL) was sonicated for 1h in an ultrasonic cleaning bath at around 35C, with monitoring of the reaction by TLC. Once the reaction finished, aqueous saturated NH4Cl solution (40mL) was added and extracted with ethyl acetate (3×20mL). The combined extracts were washed with brine (60mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the product was isolated by column chromatography with silica gel doped with 10% of KF to retain tri-n-butyltin halides formed during the reaction. 4 (0.286, 0.78mmol, 78%) eluted with 98:2 (hexane/diethyl ether).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,109-04-6, 2-Bromopyridine, and friends who are interested can also refer to it.

Reference:
Article; Gerbino, Dario C.; Fidelibus, Pablo M.; Mandolesi, Sandra D.; Ocampo, Romina A.; Scoccia, Jimena; Podesta, Julio C.; Journal of Organometallic Chemistry; vol. 741-742; 1; (2013); p. 24 – 32;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67443-38-3, 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.67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

5 -Bromo-2-methyl-3 -nitropyridineSodium hydride (1.31 g, 54.8 mmol, 2.19 g of 60% in mineral oil) was suspended in dry THF (70 mL) and to this suspension was added 5 -bromo-2-chloro-3 -nitropyridine as a solid. An ambient water bath was placed under the reaction and a solution of diethyl malonate in dry THF (15 mL) was added carefully via addition funnel. Observed a vigorous evolution of gas. After 2 hours additional sodium hydride (0.202 g, 8.42 mmol, 0.337 g of 60% in mineral oil) was added and the reaction was stirred for 1.5 hours. The reaction was concentrated in vacuo, diluted with 6N HCl (100 ml), and refluxed overnight. The reaction was concentrated in vacuo and diluted with saturated sodium carbonate until the pH = 9. The basic aqueous mixture was diluted with dichloromethane and filtered through filter paper to remove an insoluble green solid. The filtrate was transferred to a separatory funnel and the layers were separated. The dichloromethane was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated to give the title compound (5.79 g, 63.3%) as an orange oil. MS(ES)+ m/e 217 [M+H].

Statistics shows that 67443-38-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloro-3-nitropyridine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157191; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1594-58-7, 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 1594-58-7, name is N-Hydroxynicotinimidamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 15 4.7 g (5.5 ml; 55 mmol) of piperidine are added over 20 minutes to the solution of 5.1 g (4.3 ml; 55 mmol) of epichlorohydrin in 5.2 ml of tert-butanol under cooling by water while stirring vigorously. The reaction mixture is stirred at room temperature for 1 hour, then 50 ml of pure dry DMF, 6.9 g (50 mmol) of nicotinic acid amidoxime and 3.2 g (80 mmol) of powdered sodium hydroxide are added. After stirring the suspension at 70 C. for 12 hours the reaction mixture is worked up as described in Example 1 to give 13.2 g (75%) of O(3-amino-2-hydroxypropyl) nicotinic acid amidoxime dihydrochloride.

According to the analysis of related databases, 1594-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinoin Gyogyszar es Vegyeszeti Termekek Gyara Rt.; US5239077; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58584-92-2, 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 58584-92-2 as follows.

Concentrated sulfuric acid (25 mL) and 2-amino-6-chloro-nicotinic acid (4.3 g, 25 mmol) described in Production Example 4-1-1A (or 4-1-1B) were added to methanol (50 mL) while cooling with ice followed by stirring for 5 hours at 70°C. After allowing to cool on standing, the reaction mixture was neutralized with sodium bicarbonate (90 g). The resulting solid was filtered to obtain the title compound (3.2 g, 17 mmol, 68percent) as a pale brown solid. 1H-NMR spectrum (CDCl3) delta (ppm): 3.88 (3H, s), 6.62 (1 H, d J=8.2 Hz), 8.05 (1 H, d, J=8.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58584-92-2, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1864980; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52605-97-7, Adding some certain compound to certain chemical reactions, such as: 52605-97-7, name is 2,3-Dimethoxypyridine,molecular formula is C7H9NO2, 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 52605-97-7.

(c). 5-bromo-2,3-dimethoxypyridine To a solution of 2,3-dimethoxy-pyridine (104 g) in DCM (1 L) and a saturated aqueous solution of NaHC03 (1 .6 ml) at 0C was added bromine (120 g). The reaction was stirred for 2 hours at 0C. The reaction mixture was quenched with Na2S03 (saturated in water, 500 ml) and stirred for 30 min. The aqueous layer was extracted with DCM, and the organic phase was washed with brine, dried over Na2S04, filtered and concentrated. The crude product was purified by chromatography on silica gel with heptane and increasing amouts of ethyl acetate. Yield: 100 g 1H NMR delta (ppm)(CHCI3-d): 7.70 (d, 1 H, J=2.0 Hz), 7.06 (s, 1 H, J=2.0 Hz), 3.92 (s, 3H), 3.80 (s, 3H).

According to the analysis of related databases, 52605-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MSD OSS B.V.; BLACKABY, Wesley, Peter; DE KORT, Martin; ENTHOVEN, Mark; HINCHLIFFE, Paul, Stuart; PAULIE, Chris; TIMMERS, Cornelis, Marius; VERKAIK, Saskia; WO2013/41458; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66572-56-3 ,Some common heterocyclic compound, 66572-56-3, molecular formula is C6H4BrNO2, 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.

Into a 250-mL round bottom flask, was placed a solution of 2-bromoisonicotinic acid (1.4 g, 6.93 mmol, 1.20 equiv) in dichloromethane (50 mL), EDC.HCl (1.64 g, 8.56 mmol, 1.50 equiv), 4-dimethylaminopyridine (1.04 g, 8.51 mmol, 1.50 equiv), and 3-(trifluoromethyl)benzylamine (1.0 g, 5.71 mmol, 1.00 equiv). The resulting solution was stirred overnight at 25 C. in an oil bath. The resulting solution was diluted with 100 mL of dichloromethane. The resulting mixture was washed with 2*50 mL of sat. NH4Cl, 2*50 mL of sat. Na2CO3, and 2*50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:10-1:5). The product was obtained as 1.2 g (59%) of a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66572-56-3, its application will become more common.

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
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. 1824-81-3, name is 2-Amino-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Amino-6-picoline

Preparation Example 1(compound 5 and compound 13):; [Show Image] Step A Commercially available 2 amino-6-picoline (10.8 g, 100 mmol) was treated with a solution of di-tert-butyl dicarbonate (26.2 g. 120 mmol) in dichloromethane (100 mL). The solvent was removed in vacuo and the residue was heated at ?70 C in a sand bath overnight. The mixture was diluted with ethyl acetate (150 mL) and the organic phase washed with 10 % citric acid solution (70 mL), saturated sodium bicarbonate (70 mL) and brine (70 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethyl acetate/petrolether (10/90) to elute excess reagent, followed by ethylacetate/petrolether (20/80) to afford the desired compound as a colorless oil, which becomes a white solid by standing at room temperature (19 g, 91 %). 1H-NMR (400 MHz, CDCl3): d = 1.53 (s, 9H), 2.44 (s, 3H), 6.82 (d, 1H), 7.27 (br-s, 1H), 7.55 (t, 1H), 7.72 (d, 1H)

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, 1824-81-3, 2-Amino-6-picoline.

Reference:
Patent; AC Immune S.A.; EP2311823; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13091-23-1, 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.13091-23-1, name is 4-Chloro-3-nitropyridine, molecular formula is C5H3ClN2O2, molecular weight is 158.54, as common compound, the synthetic route is as follows.

Step 2. 4-Chloro-2-hydroxy-5-nitropyridine THF (500 mL) was cooled to-78 C and anhydrous NH3 (-200 mL) was condensed into the THF. Potassium t-butoxid (71.0 g, 630 mmol) was added and the mixture was allowed to warm to–35 OC. The product from Step 1 (40.0 g, 250 mmol) was cooled to 0 C in THF (200 mL) and a solution of t-BuOOH (5 M in decane, 50 mL, 250 mmol) was added over 5 min. This solution was then added dropwise to the KOt-Bu solution prepared above over 1 h, then stirred for 2 h at-35 C and then carefully quenched with-50 mL of sat. NH4C1 solution. The mixture was allowed to vent and warm to rt overnight, then the organics were concentrated and the residue made acidic with NH4Cl solution and filtered. The solid was washed with cold H20 and dried to give the title compound as a dark brown solid (35 g, 80 %).

The chemical industry reduces the impact on the environment during synthesis 13091-23-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/37197; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 800401-68-7 ,Some common heterocyclic compound, 800401-68-7, molecular formula is C8H5ClN2O2, 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.

Example 11: 5-Chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylic acid; (7-fluoro-2-oxo-l,2,3,4- tetrahydroquinolin-3-yl)amide To a suspension of 3-amino-7-fluoro-3,4-dihydro-lH-quinolin-2-one hydrochloride(Preparation 35, lOOmg, 0.4mmol) in anhydrous THF (5mL) was added DMTMM (349mg, 1.19mmol) and 4-methyl morpholine (130muL, 1.19mmol), followed by 5-chloro-lH-pyrrolo[2,3- c]pyridine-2-carboxylic acid (Preparation 3, 71mg, 0.36mmol), and the reaction stirred at rt for 16h. Solvent was concentrated in vacuo and the residue taken into EtOAc (5OmL). Organics were washed EPO with water (3OmL), IM HCl (3OmL) and brine (3OmL) before being dried (MgSO4) and removing the solvent in vacuo. Trituration from methanol afforded the title compound. deltaH(d6 DMSO): 12.35 (IH, s), 10.50 (IH, s), 9.07 (IH, d), 8.59 (IH, s), 7.78 (IH, s), 7.33-7.20 (2H, m), 6.83-6.64 (2H, m), 4.83-4.71 (IH, m), 3.11 (2H, d); m/z (ES+) = 359.06 [M+ H]+; RT = 3.44min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,800401-68-7, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem