Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 5470-18-8, 2-Chloro-3-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, 5470-18-8, blongs to pyridine-derivatives compound. Safety of 2-Chloro-3-nitropyridine

17. Preparation of 2-Hydrazino-3-nitropyridine 2-Chloro-3-nitropyridine (100 g, 0.63 mol), hydrazine monohydrate (70.4 mL, 72.6 g, 1.45 mol) and methanol (1.3 L) were mixed and heated to reflux with stirring. After 30 min the reaction mixture was cooled and filtered collecting the insoluble materials. The filtrate was concentrated by evaporation under reduced pressure and the residue obtained as well as the insoluble materials from the filtration were diluted with water. The insoluble solids present were collected by filtration, washed with water, and dried to obtain 95.2 g (98 percent of theory) of the title compound as a bright yellow powder melting at 168-169 C. Elemental Analysis C5 H6 N4 O2 Calc.: %C, 39.0; %H, 3.90; %N, 36.4; %S, 8.27 Found: %C, 39.1; %H, 4.17; %N, 36.1; %S, 8.18

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-18-8, its application will become more common.

Reference:
Patent; DowElanco; US5571775; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 86873-60-1, 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.86873-60-1, name is 5-Chloro-2-picolinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

General procedure for the preparation of amides of formula 1.4:A solution of the carboxylic acid (0.23 mmol) in methanol (5 ml) was cooled to 0 C. 4- (4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmophiholinium chloride hydrate (DMTMM) (80 mg, 0.27 mmol) was added and the solution was stirred at 0 C for 30 minutes. Thereafter, a solution of the intermediate diamine B7 (0.21 mmol) in methanol (5 ml) was added dropwise at 0 C via syringe. The reaction mixture was stirred at 23 C for 18-60 hours. For the workup, the reaction mixture was poured into a solution of sodium carbonate (1M) followed by the extraction with ethyl acetate. The organic layer was separated, washed with brine and dried over sodium sulphate. Removal of the solvent at reduced pressure left a residue which was purified by chromatography on silica gel or on a silica-NH2 phase using a mixture of dichloromethane and methanol (0-10%) to give the pure amides of formula I.Example 33(R)-N-(2′-Amino-5′,5′-difluoro-5′,6′-dihydrospiro[chroman-4,4′-[l,3]oxazine]-6-yl)-5- chloropicolinamideThe condensation of (R)-5′,5′-difluoro-5′,6′-dihydrospiro[chroman-4,4′-[l,3]oxazine]-2′,6-diamine (intermediate B7.1) and 5-chloropicolinic acid yielded the title compound (56% yield) as a white solid. MS (ISP): m/z = 409.2 [M+H]+..

The chemical industry reduces the impact on the environment during synthesis 86873-60-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; NARQUIZIAN, Robert; PINARD, Emmanuel; WOSTL, Wolfgang; WO2012/163790; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 74784-70-6, 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 74784-70-6 as follows.

Step A: 3-nitro-5-(trifluoromethyl) pyridin-2-amine To a solution of 5~(trifluoromethyl)pyridine-2-amine (l.lg, 6.79mmol) dissolved in sulfuric acid (2OmL) at room temperature was added nitric acid (0.475 g, 6.79mmol). After heating to 700C for Ihr, the reaction mixture was cooled to room temperature and diluted with EtOAc and ice. The organic layer was separated, washed with sat. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM) to give the title compound (680 mg). LC/MS: m/z 208(M+H). 1H-NMR (500MHz, CD3OD): delta 8.60 (d, 1H), 8.67 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74784-70-6, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2009/152072; (2009); 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.118399-86-3, name is 6-Bromo-2-methylpyridin-3-ol, molecular formula is C6H6BrNO, molecular weight is 188.0219, as common compound, the synthetic route is as follows.Product Details of 118399-86-3

To a 50 mL round bottom flask equipped with a stir bar was added 6-bromo-2- methylpyridin-3 -l (250 mg, 1.330 mmol), 2-(4-fluorophenyl)ethan- 1-01(186 mg, 1.330 mmol), triphenylphosphine (418 mg, 1.596 mmol) and THF (10 mL). To the stirred solutionwas added DIAD (0.310 mL, 1.596 mmol). The solution warmed to a mild reflux, then cooled within 5 minutes. The solution was stirred at r.t. for 2 hrs. The reaction solution was concentrated in vacuo and the resulting oil was diluted with a mm of acetone, then concentrated onto Celite in vacuo. The resulting powder was subjected to silica gel chromatography(40 g column, 5-40% EtOAc:Hex) to afford the product 6-bromo-3-(4-fluorophenethoxy)-2-methylpyridine (386 mg, 1.244 mmol, 94 % yield) as a white solid.?H NMR (500 MI-Tz, chloroform-d) 7.29 – 7.21 (m, 3H), 7.03 (t, J=8.7 Hz, 2H), 6.95 (d, J=8.5 Hz, 1H), 4.14 (t, J=6.6 Hz, 2H), 3.11 (t, J=6.5 Hz, 2H), 2.42 (s, 3H). ESI-MS(+) m/z = 309.9 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,118399-86-3, 6-Bromo-2-methylpyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); 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

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

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

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

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

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