Day: April 15, 2022

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

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

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 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

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

Adding a certain compound to certain chemical reactions, such as: 54232-43-8, 6-Bromo-5-methoxypicolinic 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, 54232-43-8, blongs to pyridine-derivatives compound. Computed Properties of C7H6BrNO3

4,87g (21 mmol) 6-Bromo-5-methoxy-pyridine-2-carboxylic acid and 4, 17g (25,2 mmol, 1 ,2eq) CDI are suspended in 54ml Me-THF and heated to 50C. After stirring for 3,5h at this temperature the mixture is cooled to 0C in an ice bath and 3,39ml (24,2, 1 , 15eq) triethyl-amine is added. After that 6, 1 g (23, 1 mmol, 1 , 1 eq)of (S)-3- Amino-3-(2-chloro-phenyl)-propionic acid ethyl ester are added within 20 minutes and the resulting mixture is allowed to reach RT and stirred overnight.50 ml water is added, the phases are separated and the organic phase is washed several times with 50ml of saturated NaHC03 solution followed by 50ml of 1 N HCI solution. The organic phase is evaporated in vacuo and 8,43g of product are obtained. Yield: 89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54232-43-8, its application will become more common.

Reference:
Patent; SANOFI; RUF, Sven; SADOWSKI, Thorsten; WIRTH, Klaus; SCHREUDER, Herman; BUNING, Christian; WO2012/101197; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98121-41-6, 3-Amino-5,6-dichloropyridine, 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-Amino-5,6-dichloropyridine, blongs to pyridine-derivatives compound. Quality Control of 3-Amino-5,6-dichloropyridine

Precursor alpha: 2,3-Dichloro-5-methylthiopyridine A solution of 50.6 g (0.3 mol) of 3-amino-5,6-dichloropyridine in 700 ml of methylene chloride was slowly added dropwise at 40 C. to a solution of 56.6 g (0.6 mol) of dimethyl disulfide and 46.7 g (0.45 mol) of tert-butyl nitrite in 320 ml of dry methylene chloride. The mixture was then stirred for 1 hour at 40 C. and subsequently for another approximately 15 hours at approximately 20 C., whereupon 500 ml of ice-water were added to the reaction mixture. The organic phase which was separated off was washed once with 1 N hydrochloric acid and once with water, dried over sodium sulfate and finally concentrated. After the crude product had been stirred with n-hexane, 21 g of a dark solid were obtained (purity 94% according to GC). After the hexane solution was concentrated, a further 21.3 g of product of value remained which had a purity of 77% (according to GC). Total yield: 62%; m.p.: 66-67 C.; 1H-NMR (in d6 dimethyl sulfoxide): delta [ppm]=2.6 (s, CH3); 8.1 and 8.3 (2*d, pyr H).

The synthetic route of 98121-41-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; US6448205; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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.

To a stilTed solution of 1H-indole-3-carboxaldehyde (145.2mg, lmmol) and 6- (chloromethyl)picolinonitrile (167.8mg, l.lmmol) in 5.0 mL of MeCN was added Cs2CO3(980mg, 3mmol) at room temperature. The mixture was then heated to 80C and kept stirring for 3h. When 1H-indole-3-carboxaldehyde was consumed monitored by TLC, MeCN was evaporated. The residue was partitioned in 15 mL of water and 15 mL of ethyl acetate. The aqueous layer was extracted with ethyl acetate three times. The combined organic extracts were washed with brine, dried, and concentrated. The crudeproduct was purified by silica gel colunrn chromatography to give 6-((3 -formyl- 1 H-indol1-yl)methyl)picolinonitrile (214mg, 82% yield).ESI-MS mlz 262.1 [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. 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH, CHINESE ACADEMY OF SCIENCES; JIANG, Baishan; HU, Langxi; CUI, Yan; DING, Sheng; (29 pag.)WO2015/192343; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67625-38-1, Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate, 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, name: Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate, blongs to pyridine-derivatives compound. name: Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate

A solution of ethyl 6-chloroimidazo[l,2-a]pyridine-2-carboxylate (0.8 g, 3.6 mmol), cesium carbonate (1.3 g, 3.9 mmol), palladium acetate (64 mg, 0.29 mmol), andtriphenylphosphine (0.15 g, 0.57 mmol) in 1,4-dioxane (43 mL) was treated with l-bromo-3- fluorobenzene (0.54 mL, 4.8 mmol), degassed with nitrogen, and heated in the microwave at 150 C for 30 min. The reaction mixture was filtered over celite and the filtrate was concentrated to give a crude residue. This material was purified by flash column chromatography to give the desired product (1.2 g, 94%). LCMS for C16H13C1FN202 (M+H)+: m/z = 319.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67625-38-1, Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew P.; LI, Yun-Long; YUE, Eddy W.; SPARKS, Richard B.; WO2011/75643; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185041-05-8 ,Some common heterocyclic compound, 185041-05-8, molecular formula is C7H5ClINO2, 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.

[00324] To a solution of compound 13 (5.5 g, 18.5 mmol) in DMF (50 mL) was added K2C03 (10.2 g, 74 mmol), trimethylboroxine (4.64 g, 3.70 mmol) and Pd(PPh3)4 (2.1 g, 1.85 mmol) in DMF under N2. The reaction mixture was stirred at 110 C for 120 mm under N2. After cooled down, water (100 mL) was added into the mixture. Et20 was added to extract the product, washed by water and dried over Na2SO4 .Concentrated and purified by FCC (PE/EA=40: 1) to afford 2.7 g of the product 14 (79%).

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. 185041-05-8, Methyl 2-chloro-4-iodonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; YANG, Wenjin; CHEN, Che-Hong; MOCHLY-ROSEN, Daria; WO2014/160185; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem