Month: April 2022

Synthetic Route of 1235036-15-3, 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.1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate, molecular formula is C10H11BrClNO2, molecular weight is 292.56, as common compound, the synthetic route is as follows.

Example 1E tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-bromopicolinate EXAMPLE 1D (0.736 g), EXAMPLE 1C (1.62 g), and Cs2CO3 (4.1 g) were stirred in 12 mL of anhydrous N,N-dimethylacetamide at 120 C. for 12 hours. The cooled reaction mixture was then diluted with ethyl acetate and 10% citric acid. The organic phase was washed three times with citric acid, once with water and brine, and dried over Na2SO4. Filtration and concentration afforded crude material, which was chromatographed on silica gel using 0-40% ethyl acetate in hexanes to provide the title compound.

The chemical industry reduces the impact on the environment during synthesis 1235036-15-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 878197-68-3, 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 878197-68-3, name is 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

The reactor is charged with N-methylpiperazine (3.1 Kg, 31 mol ) and tetrahydrofuran (10 Liters) and stirred under nitrogen while cooling to negative 20 0C. n-Butyl lithium (10.4 L, 26.0 mol) is added to the reaction at a rate to maintain the negative 200C temp and the contents are stirred for 15 to 30 minutes. A slurry of 5- bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (2.79 Kg, 12.4 mol) in tetrahydrofuran (10 Liters) is added at a rate to maintain the reaction at ?0C. The slurry is washed in with additional tetrahydrofuran (6 Liters). The reaction is stirred for 30 minutes and warmed to approximately negative 100C. The reaction is quenched by addition of 6N HCI solution to achieve pH 4.0 while maintaining at ? 150C. The reaction is diluted with heptane (14 Liters) and the layers allowed to separate. The lower aqueous layer is drained and the upper organic layer is washed with 1N HCI (2 x 1.5 Liters). The combined aqueous layers are stirred at 20 degrees and adjusted to pH 9 with 4N NaOH solution. The Aqueous layer is extracted with 10% iPrOH/CH2CI2 (3 x 28 Liters) and the combined organic layers are washed with saturated NaHCO3 solution (14 Liters) and evaporated at <250C to approximately 3 volumes, lsopropanol (28 Liters) is added and reaction again concentrated under reduced pressure to approximately 8.5 Liters, lsopropanol (17 Liters) is added and the reaction is treated with a solution of oxalic acid (1.0 Kg, 11.1 mol) in isopropanol (7 Liters) at a rate to maintain good stirring and temperature between approximately 25-4O0C. The reaction is stirred for 30 minutes and the solids are collected and washed with isopropanol (8.5 Liters) Solids are dried at 50 0C to yield 5-(4-methyl-1- piperazinyl)imidazo[1,2-a]pyridine-2-carbaldehyde, (2.25 Kg, 54% yield) 1H NMR (400 MHz, DMSO-D6) delta ppm 10.01 (s, 1 H) 8.47 (s, 1 H) 7.41 (m, 2 H) 6.65 (m, 1 H) 3.34 (s, 8 H) 2.78 (s, 3 H)

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 878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/87549; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6515-09-9, Adding some certain compound to certain chemical reactions, such as: 6515-09-9, name is 2,3,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 6515-09-9.

EXAMPLE 2 Preparation of 3,6-dichloro-2-(dichloromethyl)pyridine (Cpd. 2 of table) STR4 2,3,6-Trichloropyridine (1.0 g, 0.0055 mole) was combined with 4 g N-methylpyrrolidone, 4 g (0.033 mole) of chloroform, and 1.0 g of 50 percent aqueous sodium hydroxide (0.013 mole). The resulting mixture was stirred and warmed mildly for about 1 hour at which time the product was found to be present in the reaction mixture by gas chromatography and mass spectrometry using an authentic sample of the product as a standard. After standing overnight at ambient temperature the title compound represented about 1.7 percent of the pyridines in the mixture.

According to the analysis of related databases, 6515-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Dow Chemical Company; US4739070; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951625-93-7, Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-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, HPLC of Formula: C9H7ClN2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C9H7ClN2O2

To a solution of 4-chloro-1H-pyrrolo[2,3-bjpyridine-5-carboxylic acid methyl ester (0.65 g, 3.1 mmol) in DMF (6.0 mL) was added NaH (60%, 149 mg, 3.72 mmol) at 0C. The mixture was stirred at rt for lh. Mel (572 mg, 4.03 mmol) was added to the reaction and stirred at rt overnight. The reaction was quenched with sat. NH4C1 solution (10 mL) and separated between water (20 mL) and EA (30 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over anhydrous Na2SO4. The solvent was removed to give 4-chloro-1-methyl-1H-pyrrolo[2,3-bjpyridine-5-carboxylic acid methyl ester (0.75 g, yield:quantitative) as yellow crystal.?HNMR (400 MI-Tz, CDC13): = 8.86 (s, 1H), 7.26 (overlap, 1H), 6.68 (d, J= 3.6 Hz, 1H), 3.97 (s, 3H), 3.91 (s, 3H).

The synthetic route of 951625-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
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

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