Category: pyridine-derivatives

Synthetic Route of 139022-25-6, 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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid. A new synthetic method of this compound is introduced below.

A suspension of imidazo[1,2-a]pyridine-6-carboxylic acid (1.0 g), EDCI (1.775 g), HOBt (1.415 g) and N-methylmorpholine (1.0 ml) in DMF (20 ml) and DCM (5 ml) was stirred at 22C for 40 min. The resulting reddish solution was treated with diisopentylamine (1.9 ml) and N-methylmorpholine (1.0 ml) in this order and the reaction mixture was stirred at 22C for 24 h. The mixture was diluted with diethyl ether (100 ml) and washed with saturated sodium bicarbonate solution (2 x 60 ml). The combined aqueous layer was washed with diethyl ether (2 x 50 ml). The combined organic extract was washed with water (100 ml) and brine (100 ml), dried over sodium sulfate, filtered, and evaporated. The crude product was purified by column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; EP2168965; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5350-93-6, 6-Chloropyridin-3-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, 5350-93-6, blongs to pyridine-derivatives compound. name: 6-Chloropyridin-3-amine

1,1-Dimethylethyl (6-Chloro-3-pyridinyl)carbamate Di-t-butyldicarbonate (9.3 g, 43 mmol) was added to a solution of 6-chloro-3-pyridinamine (4.58 g, 35.6 mmol) in 1,4-dioxane (50 mL) and the mixture was heated under reflux for 18 h. The mixture was cooled and poured into water. The mixture was extracted with ether and the combined organic fractions were washed with water, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with hexane and the solid was collected and dried in vacuo to give the title compound as an off-white solid (7.68 g, 94%). 1H NMR (400 MHz, CDCl3) delta 8.23 (1H, s), 7.96 (1H, br d, J 7.2 Hz), 7.25 (1H, d, J 7.2 Hz), 6.54 (1H, br s), and 1.52 (9H, s). m/z (ES+) 229, 231 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5350-93-6, its application will become more common.

Reference:
Patent; Dinnell, Kevin; Elliott, Jason Matthew; Hollingworth, Gregory John; Shaw, Duncan Edward; US2002/22624; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6975-44-6, 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.6975-44-6, name is Ethyl 4,6-dihydroxynicotinate, molecular formula is C8H9NO4, molecular weight is 183.16, as common compound, the synthetic route is as follows.

(Wallace, E., et.al, ibid.)’. A stirred suspension of compound ii (1.40 g, 7.67 mmol) in phosphorus (V) oxychloride (15 mL) was heated to 110C for 2.5 h with a guard tube (CaCl2) fitted. The reaction mixture was cooled to room temperature, reduced in vacuo and the resulting dark brown residue taken up in a small volume of DCM (~ 5 mL) and transferred dropwise onto a slurry of ice in water (250 mL) whilst stirring vigorously. The aqueous mixture was extracted with EtOAc (3 x 100 mL), the organic extracts combined, dried (MgS04) and evaporated to dryness to afford the crude product as an orange gum. Column chromatography (S1O2), eluting with 15: 1 Hexanes-EtOAc, afforded compound iii. (1.33 g, 6.14 mmol, 79%) as a colourless oil; [M+H]+ m/z = 220.0.

Statistics shows that 6975-44-6 is playing an increasingly important role. we look forward to future research findings about Ethyl 4,6-dihydroxynicotinate.

Reference:
Patent; BIOTA EUROPE LTD; TYNDALL, Edward Malcolm; CZAPLEWSKI, Lloyd George; FISHWICK, Colin William Gordon; YULE, Ian Andrew; MITCHELL, Jeffrey Peter; ANDERSON, Kelly Helen; PITT, Gary Robert William; WO2013/91011; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55314-16-4, 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 55314-16-4, name is 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one. This compound has unique chemical properties. The synthetic route is as follows.

The obtained compound 3 followed by 3-(dimethylamino)-1-(pyridin-3-yl) prop-2-en-1-one (0.1 mol), guanidine nitrate(0.1 mol), sodium hydroxide (0.1 mol), and n-butanol (12.5 mL) was irradiated in the microwave synthesizer at 90 C for 20 min. Aftercompletion of the reaction mixture poured into ice-cold water andthe resulting solid was filtered and washed with water. The obtainedsolid of compound 4 (1.18 g) was dried under vacuum.Melting point 190-192 C, ES-MS (M1) found (m/z): 173.1.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 55314-16-4, 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one.

Reference:
Article; Thirumurugan; Lakshmanan, Sivalingam; Govindaraj, Dharman; Daniel Prabu, D. Sam; Ramalakshmi; Arul Antony; Journal of Molecular Structure; vol. 1171; (2018); p. 541 – 550;,
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

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

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

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

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

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