Day: July 13, 2021

Adding a certain compound to certain chemical reactions, such as: 62733-99-7, Methyl 3-hydroxypicolinate, 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, 62733-99-7, blongs to pyridine-derivatives compound. SDS of cas: 62733-99-7

To a solution of 3-hydroxy-pyridine-2-carboxylic acid methyl ester (200 mg, 1.3 mmol) in N,N-dimethylformamide (2.0 ml) was added at 22 0C sodium hydride (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0 0C and treated with trifiuoro ethyl trifiuormethanesulfonate (728 mg) and stirring was continued at 22 0C for 2 hours. The mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate, and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane and ethyl acetate (3:1) as the eluent to give 3-(2,2,2- trifluoro-ethoxy)-pyridme-2-carboxylic acid methyl ester as a pale green oil. Mass (calculated) C9H8F3NO3 [235.16]; (found) [M+H]+ = 236

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62733-99-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; ANDREINI, Matteo; BANNER, David; GUBA, Wolfgang; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; POWER, Eoin; ROGERS-EVANS, Mark; TRAVAGLI, Massimiliano; VALACCHI, Michela; WOLTERING, Thomas; WOSTL, Wolfgang; WO2011/20806; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, 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 588729-99-1.

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide 5-Bromo-2-chloro-3-pyridinamine [commercially available] (10 g, 48.2 mmol) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.46 ml, 96 mmol) added, and the mixture stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at room temperature for 5 h. A further portion of methanesulfonyl chloride (2.1 ml) was added and the mixture stirred at room temperature overnight. The pH was adjusted to ?pH6 by the addition of 2M hydrochloric acid. The mixture was then extracted with dichloromethane (2*150 ml) the combined organic layers were dried using a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M sodium hydroxide (50 ml) added. The mixture was stirred for 1 h and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and extracted with dichloromethane (150 ml). The aqueous layer was then acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give the title compound as an off white solid (13.45 g).

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

A mixture of 2-bromo-3,5-dichloropyridine (5.672 g, 25 mmol), sodium iodide (11241.7 mg, 75 mmol) and chlorotrimethylsilane (2716 mg, 25 mmol) in MeCN (50 mL) was heated under reflux for 45 min. The reaction mixture was then poured into a 2.0 M aqueous solution of sodium hydroxide (10 mL) and extracted with diethyl ether (20 mL x 3). The combined organic layers were washed with brine and evaporated to afford crude product, which was purified by biotage (EtOAc/PE=l% ~ 10%, ISCO 40 g, 25 mL/min, normal phase silica gel, uv 254) to afford the target compound 3,5- dichloro-2-iodopyridine (3800 mg, 55.5 % yield) as a white solid. 1H NMR (400 MHz, MeOD) delta 8.35 (t, J= 4.5 Hz, 1H), 8.01 (d, J= 2.3 Hz, 1H). GC-MS m/z calcd for [C5H2C12IN]: 272.9; found: 273.0.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133081-24-0, 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.133081-24-0, name is 6-Hydrazinylnicotinic acid, molecular formula is C6H7N3O2, molecular weight is 153.14, as common compound, the synthetic route is as follows.

General procedure: A 0.5M solution of 2-chloropyridine-5-carboxylic acid (15 mmol) was treated with hydrazine hydrate (150 mmol, added at once) and heated at reflux for 72 h. The suspension was concentrated to dryness. The residue was dissolved in water and acidified (pH = 3) with acetic acid. The precipitate of 2-hydrazinopyridine-5-carboxylic acid that formed in 15 min was filtered off, washed with water and air-dried. It was dissolved in the respective aliphatic carboxylic acid and the solution (0.5M) was heated at reflux for 48 h. Upon cooling to room temperature, the volatiles were removed in vacuo and the residue was triturated with 1M aqueous sodium bicarbonate. The precipitate thus formed was filtered off, washed with water and air dried. The resulting 1,2,4-triazolo[4,3-a]pyridine 12 was dissolved in methanol (0.25M and was hydrogenated over Pd(OH)2 catalyst (0.1 equiv.) at 100 atm and 100 C over 24 hours. The mixture was filtered while still hot and concentrated in vacuo. The residue was crystallized from isopropyl alcohol to provide analytically pure carboxylic acids 11a-d.

Statistics shows that 133081-24-0 is playing an increasingly important role. we look forward to future research findings about 6-Hydrazinylnicotinic acid.

Reference:
Article; Mishchuk, Alexander; Shtil, Natalia; Poberezhnyk, Mykola; Nazarenko, Konstiantyn; Savchenko, Timur; Tolmachev, Andrey; Krasavin, Mikhail; Tetrahedron Letters; vol. 57; 9; (2016); p. 1056 – 1059;,
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. 933717-10-3, name is 1H-Pyrrolo[3,2-c]pyridine-3-carboxaldehyde, the common compound, a new synthetic route is introduced below. name: 1H-Pyrrolo[3,2-c]pyridine-3-carboxaldehyde

General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification.

The synthetic route of 933717-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59237-53-5, Methyl 6-chloro-5-nitronicotinate, 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, HPLC of Formula: C7H5ClN2O4, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5ClN2O4

a Methyl 6-methylamino-5-nitro-nicotinate 1.6 g (7.4 mMol) of methyl 6-chloro-5-nitro-nicotinate (see Bernie et al. in J. Chem. Soc. 1951, 2590) were stirred in 20 ml of 40percent aqueous methylamine solution at room temperature for 30 minutes. The reaction mixture was then diluted with ice water, the yellow precipitate formed was filtered off and dried. Yield: 1.2 g (80percent of theory), Rf value: 0.66 (silica gel; ethyl acetate/ethanol/glacial acetic acid=90:5:5)

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6087380; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153034-86-7 , The common heterocyclic compound, 153034-86-7, name is 2-Chloro-4-iodopyridine, molecular formula is C5H3ClIN, 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.

(S)-5-(3-Bromophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (243 mg, 0.599 mmol) obtained in Step 1 of Example 13 was dissolved in 1,4-dioxane (7 mL), and the mixture was stirred at 100C for 2 hours after adding bis(pinacolato)diboron (0.380 g, 1.50 mol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 98.0 mg, 0.120 mmol), and potassium acetate (0.295 g, 3.00 mmol). The reaction mixture was filtered through sellite, and the filtrate was diluted withy ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography. The resulting crude product was dissolved in 1,4-dioxane/water = 4/1 (12.5 mL), and the mixture was stirred at 100C for 3 hours after adding 2-chloro-4-iodopyridine (216 mg, 0.902 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 49.0 mg, 0.060 mmol), and sodium carbonate (191 mg, 1.80 mmol). The reaction mixture was then filtered through sellite, and the filtrate was extracted with ethyl acetate. The organic layer was then washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by silica gel column chromatography to give 5-[3-(2-chloropyridin-4-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro5,8,10,10b-tetraazabenzo[e]azulen-6-one (113 mg, 43% (2 steps)). ESI-MS: m/z 438 [M + H]+. 1H NMR (CDCl3) delta(ppm) : 1.70 (m, 1H), 1.94 (m, 1H), 2.10 (m, 1H), 2.25 (m, 1H), 2.56 (s, 3H), 3.82-3.95 (m, 4H), 4.40 (m, 1H), 7.35 (dt, J = 2.02, 7.33 Hz, 1H), 7.43 (dd, J = 1.65, 5.31 Hz, 1H), 7.51-7.59 (m, 4H), 8.44 (d, J = 5.32 Hz, 1H), 8.87 (s, 1H).

The synthetic route of 153034-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 605-38-9, Adding some certain compound to certain chemical reactions, such as: 605-38-9, name is Dimethyl pyridine-2,3-dicarboxylate,molecular formula is C9H9NO4, 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 605-38-9.

80 (33.1 g, 132.8 mmol) and 2,3-pyridine carboxylic acid dimethyl ester (20.2 g, 159.3 mmol) were dissolved in dry THF (1000 mL) and dry methanol (100 mL) in a 3-necked flask with a mechanical stirrer and condenser. To this was added NaH (60percent in mineral oil, 7.01 g, 292.1 mmol) slowly in four portions. The mixture stirred until bubbling ceased, then refluxed for 24 hours. 50 mL 6 M HCl was added to the mixture while in an ice bath, stirring for 15 minutes. 200 mL diethyl ether was added, and the precipitate was filtered, and washed with diethyl ether and H2O , then dried under vacuum at 100° C. with no further purification to afford the desired product 81 (23.7 g, 50percent) as a solid: 300 MHz 1H NMR (CD3SOCD3) delta 9.05 (d, 1H), 8.75 (d, 1H), 7.8 (dd, 1H), 7.95 (d, 1H), 6.55 (s,1H), 6.45 (d, 1H), 4.65 (s, 2H), 3.8 (s, 3H), 3.7 (s, 3H); MS: 381 (M+1).

According to the analysis of related databases, 605-38-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; US2007/72831; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 888721-65-1, 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. 888721-65-1, name is 1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

To a solution of 1- (4-fluorophenyl) -6-methyl-2-oxo-l, 2- dihydropyridine-3-carboxylic acid (56.7 mg, 0.229 mmol) and N- [ 6- (4-amino-2-fluorophenoxy) -3-methylimidazo [1, 2-a] pyridin-2- yl] cyclopropanecarboxamide (60 mg, 0.176 mmol) in N, N- dimethylformamide (1 mL) were added N, N-diisopropylethylamine (61 muL, 0.352 mmol) and HATU (87 mg, 0.229 mmol), and the mixture was stirred at room temperature for 17 hr. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate alone) to give a yellow oil. The obtained oil was dissolved in ethyl acetate (1 mL) and left standing at room temperature for 17 hr. The precipitated solid was collected by filtration, washed with diethyl ether and collected by filtration to give the title compound (76 mg, 75%) as a white solid.1H-NMR (DMSOd6, 300 MHz) delta 0.78 (4H, m) , 1.74 – 1.91 (IH, m) , 2.07 (3H, s), 2.26 (3H, s) , 6.61 – 6.79 (IH, m) , 7.01 – 7.15 (2H, m) , 7.28 – 7.37 (IH, m) , 7.38 – 7.54 (5H, m) , 7.97 (IH, dd, J = 13.2, 2.5 Hz), 8.19 (IH, d, J = 1.9 Hz), 8.48 (1 H, d, J = 7.6 Hz), 10.21 (IH, br s) , 11.97 (IH, s) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,888721-65-1, 1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/136663; (2009); 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. 20265-37-6, name is 3-Methoxy-2-nitropyridine, molecular formula is C6H6N2O3, 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. category: pyridine-derivatives

Step 2: A mixture of compound 32-2 (3.2 g, 20.6 mmol), Fe (5.8 g, 130.2 mmol) and AcOH (30 mL) was stirred at room temperature for lh. The mixture was filtered and to the filtrate was added Py HBr Br2. The reaction stirred at room temperature overnight. Solvent was evaporated and the residue diluted with CH3OH. The mixture was basified to pH 7 with NaHCC>3 and evaporated. The residue was purified by column chromatography (eluent: PE/EA = 2/1) to give 32-3 as a yellow oil. LC-MS: m/z = 203.0 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 20265-37-6.

Reference:
Patent; BIOGEN IDEC MA INC.; HUTCHINGS, Richard, H.; JONES, John, Howard; CHAO, Jianhua; ENYEDY, Istvan, J.; MARCOTTE, Douglas; WO2014/28669; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem