Pyridine-derivatives

Synthetic Route of 179543-88-5, 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.179543-88-5, name is 5-Hydrazinyl-2-methoxypyridine hydrochloride, molecular formula is C6H10ClN3O, molecular weight is 175.62, as common compound, the synthetic route is as follows.

[Reference Example 5] 1-(6-Methoxy-3-pyridyl)-5-(1H-pyrrol-2-yl)pyrazole-3-carboxylic acid [Show Image] Diethyl oxalate (3.10 mL) and 1-[1-(phenylsulfonyl)-1H-pyrrol-2-yl]-1-ethanone (2.49 g) were added to a solution of sodium ethoxide (1.63 g) in ethanol (20 mL) under ice cooling, and the resultant mixture was stirred for 5 hours at room temperature. To this reaction solution, 5-hydrazino-2-methoxypyridine hydrochloride (2.52 g) of Reference Example 1 and ethanol (20 mL) were added, and the mixture was heated to reflux for 14.5 hours. After air cooling, ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added to a residue obtained by evaporating the reaction solvent under reduced pressure, and the mixture was partitioned. The aqueous layer was further extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (ethyl acetate-hexane), to obtain 1-(6-methoxy-3-pyridyl)-5-[1-(phenylsulfonyl)-1H-pyrrol-2-yl]pyrazole-3-carboxylic acid ethyl ester (3.28 g, 72%) as an oily product. To a solution of this ethyl ester product (3.28 g) in ethanol (22 mL), an aqueous 1 N sodium hydroxide solution (22 mL) was added, and the mixture was stirred for 2 days at room temperature. An aqueous 1 N hydrochloric acid solution was added to the reaction solution, and the precipitated solid was filtered, to obtain the title compound (1.40 g, 68%) as a solid. 1H-NMR(400MHz, DMSO-d6)delta: 3.94(3H, s), 5.49-5.51(1H, m), 5.98-6.00(1H, m), 6.87-6.89(1H, m), 6.98(1H, dd, J=8.8, 0.5Hz), 7.08(1H, s), 7.80(1H, dd, J=8.8, 2.7Hz), 8.25(1H, dd, J=2.7, 0.5Hz), 11.39(1H, br s). ESI-MSm/z: 285(M+H)+.

Statistics shows that 179543-88-5 is playing an increasingly important role. we look forward to future research findings about 5-Hydrazinyl-2-methoxypyridine hydrochloride.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1785418; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-02-2, 5-Bromo-4-methylpyridine-2-carboxylic acid, 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, COA of Formula: C7H6BrNO2, blongs to pyridine-derivatives compound. COA of Formula: C7H6BrNO2

Step 1: [0420] To a solution of 5-bromo-4-methylpicolinic acid (400 mg, 1.85 mmol) in dry THF (3 mL) was added borane THF complex (1M in THF, 7.4 mL, 7.4 mmol) at 0° C. and the mixture was stirred at RT overnight. The mixture was cooled to 0° C. and aqueous NH4Cl was added. The mixture was extracted with EtOAc, the combined organic layers were dried and the volatiles were removed under reduced pressure (308 mg, 82percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886365-02-2, 5-Bromo-4-methylpyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 885276-93-7, Adding some certain compound to certain chemical reactions, such as: 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate,molecular formula is C10H9BrN2O2, 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 885276-93-7.

Synthesis of Exemplary CompoundsSynthesis of ethyl 5-{{2R,4S)-4-fluoro-2-(3-fluoroDhenyl)Dyrrolidin-1-yl)Dyrazolo[1 ,5- -3-carboxylate (X- 1)[000300] A N2 purged flask was charged with ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3- carboxylate (27 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (2 mg, 2 muiotaetaomicronIota), xantphos (5 mg, 8 muiotaetaomicronIota), cesium carbonate (46 mg, 0.14 mmol), 1 ,4-dioxane (0.5 ml_) and (2R,4S)-4-fluoro-2-(3-fluorophenyl)pyrrolidine (1-6) (18 mg, 0.1 mmol). The contents were heated to 120 C for 12 hours. Upon cooling to room temperature the reaction was partitioned with EtOAc and water. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by column chromatography on silica gel withEtOAc/hexanes gradient as eluant to yield ethyl 5-((2R,4S)-4-fluoro-2-(3- fluorophenyl)pyrrolidin-1 -yl)pyrazolo[1 ,5-a]pyridine-3-carboxylate (X-1 ). 1 H NMR (400MHz, CDCI3) delta 8.20 (s, 1 H), 8.16 (d, J = 7.6 Hz, 1 H), 7.31 (td, J = 5.6, 7.6 Hz, 1 H), 7.05 (d, J = 7.6 Hz, 1 H), 6.98 (d, J = 2.8 Hz, 1 H), 6.96 – 6.91 (m, 2 H), 6.24 (dd, J = 2.8, 8.0 Hz, 1 H), 5.39 (d, J = 52.8 Hz, 1 H), 5.04 (dd, J = 7.2, 9.2 Hz, 1 H), 4.34 – 4.26 (m, 2 H), 4.17 – 3.90 (m, 2 H), 2.93 – 2.81 (m, 1 H), 2.1 1 (dddd, J = 3.6, 9.2, 13.2, 40.8 Hz, 1 H). MS m/z 372.1 (M+1 )+.

According to the analysis of related databases, 885276-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; MOLTENI, Valentina; FAN, Yi; LOREN, Jon; SMITH, Jeffrey M.; FLATT, Brenton T.; WO2012/116217; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 126553-00-2, 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.126553-00-2, name is 6-Ethylpyridin-3-amine, molecular formula is C7H10N2, molecular weight is 122.17, as common compound, the synthetic route is as follows.

3-Amino-2-chloro-6-ethylpyridine 2 g (16.4 mmol) of 5-amino-2-ethylpyridine (for the preparation see G. H. Cooper and R. L. Rickard, J. Chem. Soc. C, 3257-60 (1971) are dissolved in 17.7 ml of concentrated HCl, and 2.2 ml (21.4 mol) of 30% strength H2 O2 solution are then carefully added. An exothermic reaction starts. The temperature is kept at about 50 C. by cooling with an ice-bath, and when the reaction has subsided the mixture is subsequently stirred at this temperature for a further 15 minutes. For working up, the mixture is poured onto 200 ml of water, the pH is brought to 10 with 40% strength sodium hydroxidde solution and the mixture is extracted twice with 100 ml of methylene chloride each time. After drying with Na2 SO4, the mixture is evaporated and the residue is stirred with petroleum ether and filtered off with suction. Yield: 1.6 g (62.3% of theory) Melting point: 104 C.

Statistics shows that 126553-00-2 is playing an increasingly important role. we look forward to future research findings about 6-Ethylpyridin-3-amine.

Reference:
Patent; Bayer Aktiengesellschaft; US4988694; (1991); A;,
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. 59237-50-2, name is Methyl 5-amino-6-methoxynicotinate, molecular formula is C8H10N2O3, 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. Product Details of 59237-50-2

REFERENCE EXAMPLE 46 concentrated hydrochloric acid (9.06 ML) is added to a stirred suspension of methyl 5-amino-6-methoxynicotinate (3.3 g) in water (20 ML). The mixture is cooled to 0C and treated dropwise with a solution of sodium nitrite (1.37 g) in water (5 ML). After 30 minutes at 0C a solution of sodium tetrafluoroborate (2.84g) in water (10 ML) is added. After a further 30 minutes the precipitated diazonium salt is collected, washed with a little ice-cold water, and then with diethyl ether, and sucked dry. potassium carbonate (1.0g) is added to trifluoroacetic acid (32 ML) at 0C, followed by the addition of the diazonium salt, in one portion. The mixture is stirred at reflux for 18 hours, cooled, then poured into iced water and stirred for 1 hour. The aqueous mixture is neutralized by treatment with solid sodium bicarbonate and extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulphate, and concentrated in vacuo, to give methyl 5-hydroxy-6-methoxynicotinate (2.86 g), in the form of a beige solid. This material is used without further purification. By proceeding in a similar manner using methyl 5-amino-6-(methylthio)nicotinate instead of methyl 5-amino-6-methoxynicotinate as the starting material, there is prepared methyl 5-hydroxy-6-(methylthio)nicotinate.

With the rapid development of chemical substances, we look forward to future research findings about 59237-50-2.

Reference:
Patent; RHONE-POULENC RORER LIMITED; EP741707; (1998); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53234-55-2 ,Some common heterocyclic compound, 53234-55-2, molecular formula is C7H4N2O2, 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.

Step 15To a solution of compound 9-15 (63 mg, 0.21 mmol) in CH2C12 (2 ml) were added 5-cyanopicolinic acid hydrate (38.2 mg, 0.23 mmol), EDC (48 mg, 0.25 mmol) and 2 mmol L HC1 (aqueous solution, 0.11 ml, 0.209 mmol) at room temperature. After stirring for 1 h at the same temperature, the reaction mixture was treated with H20. The aqueous layer was extracted with AcOEt, and the organic layer was dried over MgS04, filtered and concentrated. The crude product was added to a silica gel column and eluted with hexane/EtOAc 30% to 70%. Collected fractions were evaporated to afford compound 1-35 (66 mg, 0.153 mmol, 73%) as 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,53234-55-2, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; KUSAKABE, Ken-ichi; TADANO, Genta; KOMANO, Kazuo; FUCHINO, Kouki; NAKAHARA, Kenji; WO2015/156421; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 893423-62-6, 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.893423-62-6, name is tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate, molecular formula is C11H13ClN2O3, molecular weight is 256.69, as common compound, the synthetic route is as follows.

To a solution of tert-butyl (2-chloro-3-formylpyridin-4-yl) carbamate (3-1, 30.5 g, 118.9 mmol) and l-[4-(l,3-dioxolan-2-yl)phenyl]-2-phenylethanone (3-2, 29.0 g, 108.1 mmol) in anhydrousTHF (300 mL) at room temperature was added LHMDS (IM in THF, 248 mL) in a stream. The reaction mixture was stirred at room temperature overnight and then it was refluxed for 24 hr. It was cooled and concentrated to a syrup and treated with NaHCO3 (saturated, 50 mL) and water (300 mL) to form a solid which was collected via filtration. The solid was dried, washed with ether and further dried with toluene azeotropically to give the title compound. LRMS m/z (M+1) Calcd: 389.1, found 389.1.

Statistics shows that 893423-62-6 is playing an increasingly important role. we look forward to future research findings about tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 30529-70-5, 2-Chloro-6-methylnicotinic acid, 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, COA of Formula: C7H6ClNO2, blongs to pyridine-derivatives compound. COA of Formula: C7H6ClNO2

Description 47: methyl l-chloro–methyl-S-pyridinecarboxylate (D47); To a solution of 2-chloro-6-methyl-3-pyridinecarboxylic acid (8 g, 46.6 mmol) (available from Sigma-Aldrich No.357847) in DCM (100 ml) and MeOH (50.0 ml) stirred under nitrogen at room temperature was added TMS-diazomethane 2 M in hexane (46.6 ml, 93 mmol). The reaction mixture was stirred at room temperature for 20 minutes. The solvents were removed to give the title compound D47 (7 g).MS: (ES/+) m/z: 186 (M+l) C8H8ClNO2 requires 185.1H NMR (400 MHz, CDCl3) ppm 8.10 (d, 1 H), 7.18 (d, 1 H), 3.96 (s, 3 H), 2.61 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,30529-70-5, 2-Chloro-6-methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17282-00-7, 3-Bromo-5-methylpyridin-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, Quality Control of 3-Bromo-5-methylpyridin-2-amine, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-5-methylpyridin-2-amine

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 17282-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3510-66-5 ,Some common heterocyclic compound, 3510-66-5, molecular formula is C6H6BrN, 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 solution of compound C1 (78.0 g, 456 mmol) and CuCN (45.2 g, 502 mmol) in 400 nriL of DMF was refluxed for 3 h. The mixture was concentrated under vacuum and the residue purified by chromatography on silica gel (eluent: PE/EtOAc = 10/1) to give 7.7 g of compound C2 as a white solid (Yield: 14.3percent).

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. 3510-66-5, 2-Bromo-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; KREMOSER, Claus; ABEL, Ulrich; STEENECK, Christoph; KINZEL, Olaf; WO2011/20615; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem