Category: pyridine-derivatives

Synthetic Route of 116548-04-0, 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.116548-04-0, name is 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile, molecular formula is C7H3F3N2O, molecular weight is 188.11, as common compound, the synthetic route is as follows.

2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile 1 (5.0 g, 0.03 mol) and potassium carbonate (7.3 g, 0.05 mol) were taken in dry acetone (50 mL), followed by the addition of propargyl bromide (3.1 g,0.03 mol), then catalytic amount of sodium iodide (NaI) was added. The mixture was continuously stirred for 6 to 10 h at reflux temperature. After completion of the reaction, the residue was treated with ice cold water. The solution was extracted with ethyl acetate, dried over anhydrous sodium sulphate and concentrated. The resulted residue was purified using 60-120 mesh silica gel column chromatography. Yield 74% (Pale yellow solid). m.p. 143-45C. FTIR(KBr): 3459, 3173 (amide, NH2), 2131 (C?C), 1693 (amide, CO), 1616 cm-1 (C=N); 1H NMR (CDCl3,300 MHz): delta 2.56 (t, 1H, J = 2.20 Hz, C?C-H), 5.20 (d, 2H, J = 2.20 Hz, OCH2), 6.10 (br, s, 1H, CONH2), 7.48 (d, 1H, J = 7.72 Hz, Ar-H), 7.68 (br, s, 1H,CONH2), 8.71 (d, 1H, J = 7.72 Hz, Ar-H); 13C NMR (CDCl3, 75 MHz): delta 54.29 (O-CH2), 75.56 (Acetylene-C), 76.77 (Acetylene-C), 113.99 (Ar-C), 118.80 (C-CO), 119.98 (q, J = 273.99 Hz) (CF3), 142.77(Ar-C), 146.29 (q, J = 34.11 Hz) (C-CF3), 158.31 (Ar-C-O), 163.02 (C=O); ESI-MS: m/z 245 (M+1); HRMS: m/z Calcd for C10H8F3N2O2 ([M+H]+): 245.0243. Found: 245.0231.

Statistics shows that 116548-04-0 is playing an increasingly important role. we look forward to future research findings about 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile.

Reference:
Article; Kumar, R. Naresh; Mallareddy; Nagender; Rao, P. Sambasiva; Poornachandra; Ranjithreddy; Kumar, C. Ganesh; Narsaiah; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 11; (2016); p. 1361 – 1375;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22353-40-8 , The common heterocyclic compound, 22353-40-8, name is 2,3-Dichloro-5-nitropyridine, molecular formula is C5H2Cl2N2O2, 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 2C 5-amino-2,3-dichloropyridine Anhydrous SnCl2 (300 g, 1.58 mol) and concentrated HCl (350 mL) were charged to a 5 L flask with mechanical stirrer and thermocouple. The flask was cooled in ice and the product of Example 2B (100 g, 0.518 mol) was added in portions maintaining the temperature below 65 C. After the addition was complete, the cold bath was removed, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled in ice as 25% aqueous NaOH (1000 mL) was added to bring the mixture to pH>10. The mixture was extracted with CH2Cl2 (1*600 mL, 2*400 mL) and the combined extracts were washed with brine (200 mL), dried (MgSO4), and concentrated under vacuum. The residual solid was crystallized from a mixture of water (500 mL) and ethanol (100 mL) to provide the title compound as a solid. 1H NMR (CDCl3, 300 MHz) delta 3.80 (br s, 2H), 7.10 (d, J=3 Hz, 1H), 7.77 (d, J=3 Hz, 1H); MS (DCI/NH3) m/Z 180/182/184 (M+NH4)+163/165/167 (M+H)+.

The synthetic route of 22353-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2005/261348; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 915720-71-7, 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.915720-71-7, name is (S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate, molecular formula is C12H17BrN2O2, molecular weight is 301.18, as common compound, the synthetic route is as follows.

To a stirred solution OfZnBr2 (7.85 g, 34.9 mmol) in THF (40 ml) was added cyclopropylmagnesium bromide (54.8 ml, 27.4 mmol) in THF dropwise at -78 0C. After stirring at -78 0C for 30 minutes, the resulting solution was warmed to 0 0C and stirred at EPO 0 C for 30 minutes. (S)-tert-Butyl-l-(5-biOmopyridin-2-yl)ethylcarbamate (Method 27; 3.00 g, 9.96 mmol) and Pd(PPh3)4 (0.576 g, 0.498 mmol) were added successively. The resulting mixture was stirred at 60 0C for 3 hours. After cooled to room temperature, 100 ml of saturated ammonium chloride was added, extracted with EtOAc and dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane-EtOAc = 4:1) to give the title compound as a white solid (2.04 g, 78%). 1H NMR (400 MHz) delta 8.30 (d, J= 2.0 Hz, IH), 7.37 (dd, J= 1.6 and 8.0 Hz, IH), 7.25 (d, J= 7.6 Hz , IH), 7.20 (d, J= 8.4 Hz, IH)5 4.61 (m, IH), 1.92 (m, IH), 1.37 (s, 9H), 1.29 (d, J= 12 Hz, 3H), 0.96 (m, 2H), 0.69 (m, 2H). MS: Calcd.: 262; Found: [M+H]+263.

The chemical industry reduces the impact on the environment during synthesis 915720-71-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/123113; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18368-61-1, 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. 18368-61-1, name is 2-Methyl-6-nitropyridine. A new synthetic method of this compound is introduced below.

General procedure: Into a 2 dram vial was placed 5-nitro-8-hydroxyquinonline (63 mg, 0.33 mmol), Ru/PS nanoparticle catalyst (8.0 mg, 0.477 mmol Ru/gram catalyst, 1.2 mol%), and hydrazine monohydrate (42 muL, 2.5 equiv) in 4 ml of THF. The reaction mixture was stirred for 2 hr, at which point the solvent was removed under reduced pressure. The product was extracted from the solid mixture with 3x 2 ml EtOH. The combined ethanol extracts were then passed through a short silica plug in a pipet and the silica plug was washed 2 times with 1 ml ethanol. The EtOH was then removed on a rotary evaporator under reduced pressure. The product 5-(hydroxyamino)quinolin-8-ol was isolated as an orange solid (51 mg, 0.29 mmol, 87% yield). For some of the more complex substrates, the reaction results are highly temperature sensitive, the reactions can be forced to completion by adding extra equivalents of hydrazine, and by raising the temperature to 27 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-61-1, 2-Methyl-6-nitropyridine, and friends who are interested can also refer to it.

Reference:
Article; Tyler, Jefferson H.; Nazari, S. Hadi; Patterson, Robert H.; Udumula, Venkatareddy; Smith, Stacey J.; Michaelis, David J.; Tetrahedron Letters; vol. 58; 1; (2017); p. 82 – 86;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 23612-36-4, 3-Bromo-1H-pyrrolo[3,2-c]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, 23612-36-4, blongs to pyridine-derivatives compound. Product Details of 23612-36-4

To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert-butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol). After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HCl (25, 10 mL) and brine. The organic layer was dried (Na2SO4), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90%). MS (ESI+) m/z=299 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23612-36-4, its application will become more common.

Reference:
Patent; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2013/102587; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1214328-96-7, Adding some certain compound to certain chemical reactions, such as: 1214328-96-7, name is Methyl 3-bromo-6-chloropicolinate,molecular formula is C7H5BrClNO2, 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 1214328-96-7.

At 0 C., to a solution of methyl 3-bromo-6-chloropyridine-2-carboxylate (700 mg, 2.81 mmol) in methanol (15 mL) was added sodium borohydride (534 mg, 14.06 mmol) in portions. The resulting mixture was then stirred room temperature for 4 h. The reaction was quenched with water (80 mL) carefully and the mixture was extracted with ethyl acetate (80 mL*3). The combined organic phase was washed with brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with ethyl acetate in petroleum ether (25% to 60% gradient) to yield (3-bromo-6-chloropyridin-2-yl)methanol as light yellow oil (395 mg, 64%). MS: m/z=221.8 [M+H]+.

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. 1214328-96-7, Methyl 3-bromo-6-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75806-86-9, 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.75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

Example 192: 5-Chloro-2-(2,6-dimethyl-phenoxy)-pyridin-3-ylamine; 2-Bromo-3-nitro-5-chloropyridine (4.8g, 20mmol) and 2,6-dimethylpheno. (5.Og, 41 mmol) were magnetically stirred in dry DMF (65mL) and potassium carbonate 0 was added. The mixture was heated at 50 0C for 4 days, allowed to cool to room temperature and added to ice; the product was extracted with ethyl acetate (3 x 100 mL). The extracts were washed with saturated aqueous NaHCO3 and dried (MgSO4), filtered and concentrated to provide the desired product. [00601] The nitro compound (4.5g, 16 mmol) was dissolved in glacial acetic acid (80 mL) and this solution was added dropwise to a well-stirred suspension of iron powder (4.5 g, 80 mmol) in glacial acetic acid (40 mL) heated in an oil bath at 80 0C under nitrogen. The progress of the reaction was checked by LCMS. After 20 min, the reaction was allowed to cool and was diluted with ethyl acetate (120 mL). The resulting mixture was vacuum filtered through a pad of Celite, the filter cake was washed with ethyl acetate (100 mL) and the filtrate was concentrated. The residue was slowly treated with saturated aqueous sodium bicarbonate, followed by the addition of small portions of solid sodium EPO bicarbonate to neutralize the acetic acid. The mixture was extracted using ethyl acetate (3 x 150 m._) and the extracts were dried (MgSO4), filtered and concentrated (rotovap). The product was isolated as a crystalline solid after drying (vacuum), mass spectrum m/z 251.3 (M + H).

The chemical industry reduces the impact on the environment during synthesis 75806-86-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1133879-69-2, Adding some certain compound to certain chemical reactions, such as: 1133879-69-2, name is 3-Fluoro-5-vinylpyridine,molecular formula is C7H6FN, 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 1133879-69-2.

A mixture of carboline 2 (1 mmol), vinylpyridine 3a (1 mmol), CsF (0.1 g), hydroquinone(0.02 g), and DMSO (1.5 mL) was heated with stirring for 6 h at 150-160 C and then concentrated in vacuo (3 Torr). The residue was extracted with CH2Cl2, and the solution was concentrated. The product was isolated by chromatography on silica gel(260 mesh) using MeOH-CHCl3, 1 : 10, as the eluent. Yield 2.6 g (80%). M.p. 103-104 C. 1H NMR (CDCl3), delta: 2.44 (s, 3 H,Me); 2.49-2.56 (m, 5 H, CH2 and MeN); 2.72 (t, 2 H, CH2, 3JH,H = 6.1 Hz); 3.01 (t, 2 H, CH2, 3JH,H = 6.0 Hz); 3.65 (s, 2 H, CH2); 4.20 (t, 2 H, CH2, 3JH,H = 6.0 Hz); 6.88 (dt, 1 H, CHPy, 3JH,F = 9.1 Hz, 4JH,H = 1.9 Hz); 6.98 (d, 1 H, CHInd, 3JH,H = 8.4 Hz); 7.10 (d, 1 H, CHInd, 3JH,H = 8.4 Hz); 7.20 (s, 1 H, CHInd); 8.11 (t, 1 H, CHPy, 4JH,H = 1.9 Hz); 8.32 (d, 1 H, CHPy, 4JH,H = 1.9 Hz). 13C NMR (CDCl3), delta: 21.2, 22.5, 32.8, 43.6, 45.4, 51.4, 52.1, 107.6, 108.1, 117.5, 122.1, 122.8 (d, CPy(4), 2JC,F = 18 Hz); 125.9, 128.0, 132.5, 134.0, 135.6 (d, CPy(3), 3JC,F = 3 Hz); 136.1 (d, CPy(6), 2JC,F = 23 Hz); 145.5 (d, CPy(2), 3JC,F = 4 Hz); 156.4, 161.5 (d, CPy(5), 1JC,F = 257 Hz). 19F NMR (CDCl3), delta: -47.5 (d, 3JF,H = 9.1 Hz). Rf 0.46 (CHCl3-MeOH,10 : 1). Found (%): C, 74.41; H, 6.68; N, 12.79. C20H22FN3. Calculated (%): C, 74.28; H, 6.86; N, 12.99.

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. 1133879-69-2, 3-Fluoro-5-vinylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Aksinenko, A. Yu.; Bachurin, S. O.; Maleev, G. V.; Nebogatikov, V. O.; Shevtsova, E. F.; Ustyugov, A. A.; Vasil?eva, N. A.; Vikharev, Yu. B.; Russian Chemical Bulletin; vol. 69; 4; (2020); p. 781 – 786; Izv. Akad. Nauk, Ser. Khim.; 4; (2020); p. 781 – 786,6;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 31181-88-1, name is 5-Fluoropicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Fluoropicolinaldehyde

a) 2-Ethynyl-5-fluoro-pyridineTo a mixture of 5-fluoro-2-formylpyridine (1.10 g, 9.0 mmol) in MeOH (38 mL) was added potassium carbonate (2.44 g, 0.018 mol) followed by a solution of (l-diazo-2-oxo-propyl)- phosphonic acid dimethyl ester (2.03 g, 11 mmol) in MeOH (12 mL). The mixture was stirred at room temperature for 90 min, then extracted with diethylether. The organic layers were then washed with sodium hydrogen carbonate solution (1 M) and brine, dried over sodium sulfate, filtered and evaporated at to give the title compound (1.01 g, 78%) as a light brown liquid. MS: m/e = 121.0 [M]+.

With the rapid development of chemical substances, we look forward to future research findings about 31181-88-1.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERNANDEZ, Maria-Clemencia; LUCAS, Matthew C.; THOMAS, Andrew; WO2012/62687; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1071727-78-0 ,Some common heterocyclic compound, 1071727-78-0, molecular formula is C9H10N2O, 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.

6,7-Dihydro-5H-[1]pyrindin-7-ylamine: 5,6-Dihydro-[1]pyrindin-7-one O-methyl-oxime (4.1 g, 25.28 mmol) and Pd/C (150 mg) were mixed in TFA and then resulting reaction mixture was hydrogenated under 50 psi for 14 hours. Filtration via celite and concentration afforded the desired title amine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 1.89-2.02 (m, 1H), 2.46-2.58 (m, 1H), 2.89-3.01 (m, 2H), 4.62-4.73 (m, 1H), 7.30-7.37 (m, 1H), 7.77 (d, J=7.62 Hz, 1H), 8.35-8.50 (m, 3H).

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. 1071727-78-0, (Z)-5H-Cyclopenta[b]pyridin-7(6H)-one O-methyl oxime, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Allergan, Inc.; US2008/255239; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem