Day: April 19, 2022

Adding a certain compound to certain chemical reactions, such as: 27652-89-7, (4-Chlorophenyl)(pyridin-2-yl)methanol, 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, 27652-89-7, blongs to pyridine-derivatives compound. category: pyridine-derivatives

The compounds of the present invention were synthesized according to the procedure, which is illustrated schematically in FIG. 1 for three MPH alkyl analogs. Referring to FIG. 1, para-bromochlorobenzene 1 was converted into a Grignard reagent with Mg/THF which was then reacted with the pyridine-2-carboxaldehyde 2 to produce the alcohol 3. The alcohol 3 was oxidized with pyridinium chlorochromate in CH2Cl2 to produce the ketone 4. The ketone 4 was then reacted with a Grignard reagent that contains the required R group to produce the alcohol 5. After dehydration with refluxing HCl, the resulting Z and E olefin mixture 6 was hydrogenated with 10% Pt/C in HOAc containing 3% CF3COOH to produce the final compounds 7 with a ratio of about 40:60 of the R,R/S,S and R,S/S,R racemates for the ethyl compound. The racemates were separated by column chromatography and their relative configurations were determined by x-ray crystallography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27652-89-7, its application will become more common.

Reference:
Patent; Froimowitz, Mark; Kelley, Charles J.; US2006/100243; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 603311-76-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 603311-76-8 as follows.

Add 0. 5M diisobutylaluminum hydride in toluene (4.6 mL, 2.29 mmol) to a solution of (6-bromo-imidazo [1, 2-a] pyridin-3-yl) -acetic acid ethyl ester (0.65 g, 2.29 mmol) and morpholine (5 mL) in THF (40 mL) AT-78 C. Gently warm the reaction to room temperature and dilute carefully with methanol. Filter and concentrate the filtrate. Flash chromatography gives the subtitled compound (0.24 g, 32percent) as a white solid. MS ES+m/e 324.0, 326.0 (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,603311-76-8, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/50659; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1156542-25-4, 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. 1156542-25-4, name is 6-Chloro-4-(trifluoromethyl)picolinonitrile. A new synthetic method of this compound is introduced below.

A 2 dram vial containing (S)-N-((1R,2R,4S)-7-cyano-7-azabicyclo[2.2.1]heptan-2-yl)pyrrolidme- 3 -carboxamide hydrochloride (0 2 mmol) was added 6-chloro-4-(trifluoromethyl)picolitionitrile (62.0 mg, 0 300 mmoi), acetonitrile (667 m) and DIPEA (140 m, 0.800 mmol). The suspension was stirred at 60 C for 2h when LC-MS showed good conversion (80%). The reaction was purified via RP- HPLC with 0.1% NH40H in ACN and water as mobile phase to afford (S)-l-(6-cyano-4- (trifluoromethyl)pytidin-2-yl)-N-((lR,2R 4S)-7-cyano-7-azabicyclo[2.2.1]heptan-2-yl)pyirolidine-3- carboxamide in 41% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1156542-25-4, 6-Chloro-4-(trifluoromethyl)picolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CARMOT THERAPEUTICS, INC.; BUTLER, John R.; ERLANSON, Daniel; GRACEFFA, Russell; IWIG, Jeffrey; JEONG, Joon Won; WHITE, Ryan D.; WU, Yongwei; YI, Shuyan; BANERJEE, Abhisek; MCFARLAND, Jesse M.; ZHENG, Xiao Mei; (307 pag.)WO2020/36940; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1097264-89-5, name is 2-Chloro-5-fluoro-3-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of 2-chloro-5-fluoro-3-(methyloxy)pyridine D47 (0.11 g, 0.70 mmol) in dry toluene (3 ml), sodium t-butoxide (0.094 g, 0.98 mmol), Pd2(dba)3 (0.064 g, 0.07 mmol), BINAP (0.131 g, 0.21 mmol) and benzophenone imine (0.14 ml, 0.84 mmol) were added. The resulting mixture was degassed (3×pump/N2) and then heated to 80 C. After 1 h stirring, the mixture was cooled down to room temperature, diluted with Et2O (80 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (8 ml) and HCl (0.35 ml of a 2 M aqueous solution, 0.70 mmol) was added. The mixture was stirred at room temperature for 1.5 h, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (40 ml). The phases were separated and the aqueous one back-extracted with DCM (2×10 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M, Cy/EtOAc 60/40) to give the title compound D48 (0.071 g, 0.49 mmol, 70% yield from D47, two steps) as a yellow solid. UPLC: rt=0.28 min, peak observed: 143 (M+1). C6H7FN2O requires 142.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1097264-89-5, 2-Chloro-5-fluoro-3-methoxypyridine.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 887266-57-1, Adding some certain compound to certain chemical reactions, such as: 887266-57-1, name is 3-Fluoro-2-hydrazinylpyridine,molecular formula is C5H6FN3, 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 887266-57-1.

A solution of methyl 2- {3 -(4-chlorophenyl)-5-oxo-4- [(2-3,3 ,3 -trifluoro-2-hydroxypropyl] -4,5-dihydro-1H-1,2,4-triazol-1-yl}ethanimidate (Example 7A, 1.00 g, 2.64 mmol) in tetrahydrofuran(20 ml) was cooled to 0C and treated with methyl chloro(oxo)acetate (270 jil, 2.9 mmol). Theresulting mixture was stirred for 30 mm. 3 -Fluoro-2-hydrazinylpyridine (369 mg, 2.90 mmol) andN,N-diisopropylethylamine (510 jil, 2.9 mmol) were added, the reaction mixture was warmed up toroom temperature and stirred for 1 h, followed by 1 h at 120C in a sealed vial under microwave irradiation. The crude product was purified by preparative HPLC (Method 5). Lyophilisation of the product containing fractions afforded 680 mg (48% of th.) of the title compound.LC-MS (Method 3): R = 1.78 mm; MS (ESIpos): mlz = 542 [M+H]1H-NMR (400 MHz, DMSO-d6) [ppm]: 3.808 (16.00), 3.821 (1.05), 3.844 (0.95), 3.857 (1.15),3.881 (1.24), 3.990 (1.20), 3.998 (1.28), 4.027 (0.81), 4.035 (0.78), 5.217 (8.13), 6.907 (2.33),6.923 (2.34), 7.614 (3.78), 7.618 (1.47), 7.630 (1.62), 7.635 (5.20), 7.751 (5.36), 7.756 (1.78),7.768 (1.53), 7.773 (3.96), 7.794 (0.74), 7.806 (1.20), 7.816 (1.57), 7.827 (1.42), 7.837 (0.87), 8.135 (0.90), 8.138 (0.95), 8.156 (1.02), 8.159 (1.71), 8.162 (1.23), 8.180 (0.81), 8.184 (0.82),8.485 (1.74), 8.496 (1.69).

According to the analysis of related databases, 887266-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; TINEL, Hanna; SCHMECK, Carsten; WASNAIRE, Pierre; SCHIRMER, Heiko; LUSTIG, Klemens; (205 pag.)WO2019/81299; (2019); 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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine, molecular formula is C8H7BrN2, 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. Recommanded Product: 116355-18-1

Step 2: To a solution of 6-bromo-7-methylimidazo(l,2-a)pyridine (9 g, 43.0 mmol) and anhydrous sodium acetate (9.52 g, 116.1 mmol) in MeOH (100 mL) at 0 C was added iodine (12.0 g, 47.3 mmol). The reaction mixture was stirred at rt for 20 h. The precipitate was collected by filtration and washed with MeOH to afford 6-bromo-3-iodo-7- methylimidazo[l,2-a]pyridine (6 g, 41%) as a light grey solid. 1H NMR (400 MHz, CDC13) delta 8.30 (s, 1H), 7.64 (s, 1H) 7.49 (s, 1H) 2.50 (s, 3H); MS (ESI) m/z 336.7 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); 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. 94170-15-7, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, molecular formula is C7H7NO2, 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. COA of Formula: C7H7NO2

1- (1,1-dioxotetrahydro-2H-thian-4-yl) -6-((trans) -4-methylpyrrolidin-3-yl) -1,5-dihydro -4H-pyrazolo [3,4-d] pyrimidin-4-one trifluoroacetate (97mg, 0.21mmol, 1.0eq),1-methyl-2-oxo-1,2-dihydropyridine-4-carboxaldehyde (34.2 mg, 0.25 mmol, 1.2 eq)And acetic acid (25mg, 0.42mmol, 2.0eq) were dissolved in methanol (5mL), heated to 45 C for 2h,Cool down to 0 ,Add sodium cyanoborohydride (39.2 mg, 0.63 mmol, 3.0 eq) and stir at this temperature for 2 h.TLC monitoring showed no complete reaction,Additional 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxaldehyde (114.3mg, 0.83mmol, 4.0eq) was added and stirred at this temperature for 2h,Add cyanoborohydride (39.2mg, 0.63mmol, 3.0eq), and react at 45 C for 2h.TLC monitoring showed complete reaction,Concentrated under reduced pressure, added saturated aqueous sodium carbonate (10 mL) and saturated brine (10 mL), and extracted with dichloromethane (50 mL x 4). The organic phases were combined, dried, filtered, and concentrated.The crude product was purified by preparative thin layer chromatography (MeOH: DCM = 1: 20)The product was obtained as an off-white solid (59 mg, yield: 45.6%).

With the rapid development of chemical substances, we look forward to future research findings about 94170-15-7.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Peng Peng; Li Lin; (59 pag.)CN110357888; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1149-24-2, 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1149-24-2, its application will become more common.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-45-5 ,Some common heterocyclic compound, 884494-45-5, molecular formula is C6H5FIN, 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 mixture of racemic 1-(1H-indazol-6-yl)spiro[2.2lpentane-1-carbonitrile (300 mg, 1.43 mmol) (Q.3), 2-fluoro-4-iodo-6-methylpyridine (510 mg, 2.15 mmol), trans-N ,N?-dimethyl- 1,2-cyclohexanediamine (61.2 mg, 0.430 mmol), copper(I) iodide (82 mg, 0.43 mmol), and cesium carbonate (934 mg, 2.87 mmol) in a 20 mL microwave vial, was added DMSO (2 mL). The vial was sealed, degassed and backfilled with nitrogen (3x) and stirred at 50C overnight. The mixture was diluted with water (5 mL), and extracted with DCM (3 x 5 mL). The organic extracts were combined, dried over MgSO4 and concentrated to dryness. The residue waspurified by silica gel column chromatography (gradient elution: 0-50% EtOAc)/hexanes).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-45-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CANDITO, David Annunziato; GRAHAM, Thomas, H.; ACTON, John; CHAU, Ryan Wing-Kun; CHEN, Joanna, L.; ELLIS, J. Michael; FULLER, Peter, H.; GULATI, Anmol; GUNAYDIN, Hakan; KATTAR, Solomon; KEYLOR, Mitchell Henry; LAPOINTE, Blair, T.; LIU, Ping; LIU, Weiguo; METHOT, Joey, L.; NEELAMKAVIL, Santhosh, F.; SIMOV, Vladimir; TONG, Ling; WOOD, Harold, B.; (154 pag.)WO2019/74809; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine, molecular formula is C7H6N2OS, molecular weight is 166.2, as common compound, the synthetic route is as follows.category: pyridine-derivatives

EXAMPLE 27 4-OXAZOLO[4,5-b]PYRIDIN-2-YL-1,4-DIAZA-BICYCLO[3.2.2]NONANE The title compound was prepared from 2-(methylthio)oxazolo[4,5-b]pyridine (J. Org. Chem. 1995, 60, 5721) by the procedure described in Example 9 in 98% yield: 1H NMR (CDCl3, 400 MHz) delta 8.14 (dd, 1H, J=5.0, 1.2 Hz), 7.34 (dd, 1H, J=7.5, 1.2 Hz), 6.81 (dd, 1H, J=7.8, 5.0 Hz), 4.50 (s, 1H), 3.90 (t, 2H, J=5.8 Hz), 3.13-3.05 (m, 4H), 2.98-2.91 (m, 2H), 2.13-2.05 (m, 2H), 1.79-1.71 (m, 2H); 13C NMR (CDCl3, 100 MHz) delta 163.1, 158.7, 144.7, 141.4, 115.4, 114.8, 57.1, 50.6, 46.4, 46.3, 44.4, 30.3, 26.9; MS (Cl) m/z 245.2 (M+1); HPLC retention time=1.38 min. The hydrochloride salt was prepared by diluting in ethyl acetate and adding a 2.5 N HCl solution in ethyl acetate: mp>300 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,169205-95-2, 2-(Methylthio)oxazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; O’Neill, Brian Thomas; Coe, Jotham Wadsworth; O’Donnell, Christopher John; US2002/86871; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem