Month: January 2021

Related Products of 179897-89-3, A common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

5-bromo-2-fluoro-benzonitrile (12.4 mmol, 2470 mg) in pyridine (6.5 mL) was treated with ammonium sulfide (40 mass% in water, 1.1 equiv., 13.6 mmol, 2.32 mL) and triethylamine (1.1 equiv. , 13.6 mmol, 1.90 mL). The reaction mixture was heated at 50 C for 3 hours, then cooled to room temperature. The reaction mixture was partitioned between EtOAc and water. The organic later was washed with water (3x), and brine (3x), dried with MgS04, then concentrated. The residue was purified on silica eluted with 0 to 50% EtOAc in Heptane to provide 5-bromo-2-fluoro-benzenecarbothioamide (2.84 g, 94% yield). A mixture of 5-bromo-2-fluoro-benzenecarbothioamide (11.8 mmol, 2840 mg) and ethyl bromopyruvate (1.05 equiv., 12.4 mmol, 1.56 mL) in ethanol (30 mL) was heated at 80 C overnight. The mixture was concentrated and the residue was purified on silica eluted with 0 to 20% EtOAc in Heptane to afford ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4- carboxylate (2960 mg, 76.14% Yield) as a clear oil. To a solution of ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylate (8.97 mmol, 2960 mg) in methanol (40 mL) and water (10 mL) was added lithium hydroxide (1.6 equiv., 14.2 mmol, 347 mg) . The reaction mixture was stirred at 50 C for 2 hours. The reaction mixture was cooled to room temperature, concentrated, suspended in water, and then quenched with 2N HCl(aq.). The solid was collected, washed with water, and dried under high vacuum to afford 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylic acid (2410 mg, 89% Yield) as a white solid. -(6-(trifluoromethyl)pyridin-2-yl)thiazole-4-carboxylic acid

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BURCH, Jason; CHEN, Huifen; WANG, Xiaojing; WO2015/140189; (2015); A1;,
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Related Products of 2973-50-4,Some common heterocyclic compound, 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile, molecular formula is C8H8N2, 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.

(2-Aminophenyl)acetonitrile (9) (2.64 g, 20.0 mmol) was dissolved in 50 mL of acetic acid. KI (3.65 g, 22.0 mmol) was added followed by dropwise addition of 30% H2O2 (2.24 mL, 22.0 mmol). The reaction mixture was then stirred under nitrogen for 90 min, poured into 200 mL of 0.1 M sodium thiosulfate solution, and extracted with ethyl acetate (3 ¡Á 200 mL). The organic fractions were combined, washed with 0.1 M sodium thiosulfate (2 ¡Á 200 mL), satd sodium bicarbonate (2 ¡Á 200 mL) and brine (2 ¡Á 200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by automated flash chromatography (400 g silica gel, 25% ethyl acetate/hexanes) afforded 10 (3.5 g, 68%). 1H NMR (400 MHz, DMSO-d6) delta ppm: 5.41 (s, 2H), 6.53 (d, J = 8.34 Hz, 1H), 7.30 (dd, J = 8.59, 2.02 Hz, 1H), 7.39 (d, J = 2.02 Hz, 1H), NH2 protons not resolved.

The synthetic route of 2973-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobko, Mark A.; Evans, Karen A.; Kaura, Arun C.; Shuster, Leanna E.; Su, Dai-Shi; Tetrahedron Letters; vol. 53; 2; (2012); p. 200 – 202;,
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These common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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. SDS of cas: 4592-94-3

General procedure: To a stirred solution of 3-oxo-3-aryl-propionitriles 2 and Et3N (0.101 g, 1 mmol) inCH3OH:H2O (2:1, 6 mL) was added adducts of ninhydrin and malononitrile 9 (0.208 g, 1 mmol)at room temperature. After completion of the reaction [about 30-120 min, TLC (n-hexan/EtOAc,2:1) monitoring], the solvent was evaporated under vacuum and the crude product wascrystallized from CH2Cl2/n-hexan.

The synthetic route of 3-(4-Bromophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yavari, Issa; Khajeh-Khezri, Aliyeh; Bahemmat, Samira; Halvagar, Mohammad Reza; Synlett; vol. 28; 14; (2017); p. 1785 – 1788;,
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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. 39581-21-0, name is N-Butyl-2-cyano-acetamide, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

General procedure: A mixture of a salicylaldehyde (1a or 1b, 1 mmol), N-alkyl-2-cyanoacetamides (2a-2f,1 mmol), and {Mo132} (0.05 g) was heated in an oil bath at 110 C for 5-15 min. Aftercompletion of the reaction, monitored by TLC on silica gel (n-hexane-ethyl acetate,3:2), the mixture was cooled to room temperature and hot ethanol (10 ml) was added.The catalyst was collected by filtration and washed with a small portion of hot ethanol(5 ml). The combined filtrate was concentrated by half and allowed to stand at roomtemperature. The precipitated solid was collected by filtration, and recrystallized from96% ethanol to give compounds 3a-3i in high yields (see Table 2).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Jooya, Arsalan; Davoodnia, Abolghasem; Fattahi, Mehri; Tavakoli-Hoseini, Niloofar; Organic Preparations and Procedures International; vol. 50; 6; (2018); p. 565 – 574;,
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Reference of 20099-89-2,Some common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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.

General procedure: A solution of 1a or 1b (0.001 mol) in acetone (10 mL), an appropriate substituted 2-bromoacetophenone derivative (0.001 mol) and potassium carbonate (0.138 g, 0.001 mol) were reuxed at 40 C for 12 h. The solvent was evaporated, residue was washed with water, dried and recrystallized from ethanol. The mass spectra of the compounds (3a-p) are available in the Supplementary Materials.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Bromoacetyl)benzonitrile, its application will become more common.

Reference:
Article; Cevik, Ulviye Acar; Saglik, Beguem Nurpelin; Levent, Serkan; Osmaniye, Derya; Cavu?oglu, Betul Kaya; Ozkay, Yusuf; Kaplancikli, Zafer Asim; Molecules; vol. 24; 5; (2019);,
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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. 105-34-0, name is Methyl 2-cyanoacetate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H5NO2

A mixture of cyano-acetic acid methyl ester (1 1 g, 11 1 mmol), CS2CO3 (108 g, 333 mmol) and methyl iodide (35 mL, 556 mmol) in anhydrous DMF (300 mL) was stirred at r.t. for 3 days. Brine (100 mL) and ether (250 mL) were added, and the aqueous layer was extracted with additional ether (250 mL). The organic layers were combined, washed with water (4 x 200 mL), and dried over MgSO/t. The solvent was evaporated to give 1 1 g of the title compound as a yellow oil. lH NMR (CDCI3, 200 MHz): 8ppm= 3.83 (s, 3H), 1.63 (s, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 105-34-0.

Reference:
Patent; FIBROGEN, INC.; HO, Wen-Bin; ZHAO, Hongda; DENG, Shaojiang; NG, Danny; WRIGHT, Lee R.; WU, Min; ZHOU, Xiaoti; AREND, Michael P.; FLIPPIN, Lee A.; WO2013/134660; (2013); A1;,
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Electric Literature of 3759-28-2,Some common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, molecular formula is C9H6N2, 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.

General procedure: To a solution of homophthalonitrile 2 (129 mg, 0.82 mmol) in PriOH (4 ml), salicylaldehyde 1 (2.46 mmol) and NH4OAc (143 mg, 1.64 mmol) were added. The mixture was placed into a microwave reactor and heated at 150 C for 10 min. The vessel was opened, MeNO2 (0.439 ml, 8.2 mmol) and Et3N (0.114 ml, 0.82 mmol) were added, the mixture was heated again in the microwave reactor at 150 C for 10 min. The solvent was evaporated under reduced pressure, the residue was chromatographed on silica gel (EtOAc-hexane, 1:5-1:1) (method A) or was dissolved in asmall volume of Et2O or CH2Cl2 and extracted with HCl aqueous solution(0.6 m, 3 30 ml). The aqueous layer was neutralized with Na2CO3. The precipitate was filtered off and washed with H2O several times and once with a small amount (1.5 ml) of PriOH and dried in air (method B).

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

Reference:
Article; Festa, Alexey A.; Storozhenko, Olga A.; Bella Ndoutoume, Delphine R.; Varlamov, Alexey V.; Voskressensky, Leonid G.; Mendeleev Communications; vol. 27; 5; (2017); p. 451 – 453;,
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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. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-4-fluoro-3-methylbenzonitrile

Example 4 2-Chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methylbenzonitrile, hydrochloride (165RL90) 2-Chloro-4-fluoro-3-methylbenzonitrile (165RL87a, 55 mg, 0.32 mmol) and nortropine (165 mg, 1.29 mmol) was dissolved in pyridine (2 mL) and the mixture irradiated at 220 C. for 2 hours in a microwave oven. Dichloromethane (50 mL) was added and the mixture washed with hydrochloric acid (0.4 M, 2¡Á30 mL) followed by sat. sodium hydrogen carbonate (20 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The product was further purified by column chromatography using dichloromethane to give the title compound (16.2 mg, 18%). Rf=0.45 (CH2Cl2). LC/MS m/z 277 [M+H]+. 1H-NMR (CDCl3, 300 MHz) delta 7.37 (d, 1H, J=8.6, Ar-H), 6.78 (d, 1H, J=8.6, Ar-H), 4.20 (m, 1H, Tr-H), 3.80 (m, 2H, Tr-H), 2.37 (s, 3H, Ar-CH3), 2.32-2.22 (m, 4H, Tr-H), 1.98-1,81 (m, 4H, Tr-H).

The synthetic route of 796600-15-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schlienger, Nathalie; Thygesen, Mikkel Boas; Pawlas, Jan; Badalassi, Fabrizio; Lewinsky, Rasmus; Lund, Birgitte Winther; Olsson, Roger; US2006/160845; (2006); A1;,
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These common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, 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. SDS of cas: 555-21-5

To a solution of (4-nitro-phenyl)-acetonitrile (5.00 g; 30.9 mmol) in dry DMF (30 mL) cooled at 0 C, under N2 atmosphere, was added NaH (60% dispersion in mineral oil; 1.23 g; 30.9 mmol) portionwise and the mixture was stirred for 15 min at 0C. Then iodomethane (1.92 mL; 30.9 mmol) was added and the mixture was stirred at room temperature for 1.5 hour. The reaction was re-cooled at 0C and NaH (60% dispersion in mineral oil; 1.23 g; 30.9 mmol) was added again portionwise. After stirring at 00C for 15 min, iodomethane (1.92 mL; 30.9 mmol) was added and the reaction was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the residue was taken up with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The crude was purified by chromatography [SiO2, Petroleum ether/EtOAc (95/5 to 8/2)] to give the title compound as a yellow solid (3.50 g, 60 % yield). LCMS (RT): 1.42 min (Method A); MS (ES+) gave m/z: 191.1 (MH+).

The synthetic route of 4-Nitrophenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
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Synthetic Route of 874472-98-7, 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 874472-98-7 as follows.

To prepare compound 109, first 2-Methoxy-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile was prepared by combining 3-bromo-2-cyanobenzonitrile (1.0 g), P(cyclohexyl)2biphenyl (200 mg), Pd2dbas (132 mg) and flushing with nitrogen. Then dioxane (32 mL), triethylamine (2.7 mL) and pinacolborane (1.5 mL) was added and the mixture heated at reflux. After 16 h, the reaction was quenched with saturated ammonium chloride, and extracted with EtOAc. The organic layers were washed with brine, dried over magnesium sulfate, an filtered. Flash chromatography (80% dichloromethane/hexanes) affords 2-methoxy-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile (416 nig)

According to the analysis of related databases, 874472-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIGAND PHARMACEUTICALS, INC.; WO2006/10142; (2006); A2;,
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