Tag: M.W=200-300

Application of 17823-40-4,Some common heterocyclic compound, 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, molecular formula is C7BrF4N, 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.

A mixture of 4-bromo-2,3,5,6-tetrafluorobenzonitrile (2.2 g, 5.53 mmol), 2-cyanopyridine-5-boronic acid pinacol ester (2.0 g, 5.53 mmol), Pd2(dba)3 (0.18 g, 0.2 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.16 g, 0.4 mmol) and K3PO4 (2.2 g, 10 mmol) in anhydrous toluene (100 ml) was degassed and heated at 115 C for 16 hours. The resulting mixture was poured into ethyl acetate (100 ml), after filtered off precipitate, the solution was loaded on silica gel and purified by flash column using eluents of ethyl acetate/hexane (10% to 30%). The desired fractions were collected and concentrated to give white solid (Compound25) (0.18 g, in 6% yield).

The synthetic route of 17823-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 79463-77-7, 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3,4-difluoroaniline (646 mg, 5 mmol) in isopropanol (10 mL) was added diphenyl cyanocarbonimidate (1.19 g, 5 mmol) and the suspension was stirred at room temperature over night. The precipitate was filtered off, washed with isopropanol and dried under reduced pressure to yield the title compound as a white solid (1.18 g, 86%).MS ISP (m/e): 274.1 (100) [(M+H)+].1H NMR (DMSO-D6, 300 MHz): 5(ppm) = 10.92 (s, 1H), 7.65 (m, 1H), 7.43 (m, 3H), 7.29 (m, 4H).

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; FLOHR, Alexander; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/101304; (2011); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 75344-77-3,Some common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

In a microwave vial, methyl 2-((S)-6-((R)-7-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-2,3-dihydro-1 H-inden-1 -yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (200 mg), 4-bromo-3,5-dimethylbenzonitrile (90 mg), K3PO4 (273 mg), Palladium-(ll)- acetate (10 mg) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S-Phos) (17 mg) are suspended in toluene (10 mL) and water (2 mL) and purged for 10 minutes with argon. The vial is sealed and the mixture is stirred at 100C for 4 hours. After cooling to ambient temperature the mixture is partitioned between ethyl acetate and water. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10) to give the title compound. Yield: 85 mg; LC (method 19): tR = 1 .52 min; Mass spectrum (EST): m/z = 471 [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 4-Bromo-3,5-dimethylbenzonitrile, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144098; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 179898-34-1, A common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-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.

Example 57 3′-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile 3-Bromo-5-fluorobenzonitrile (5.00 g, 25.0 mmol), Pd(OAc)2 (0.15 g), PPh3 (0.60 g) and K2CO3 (5.18 g, 37.5 mmol) were dissolved in dioxane (60 mL). The mixture was heated at 70 C. for 30 min, then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (7.99 g, 30.0 mmol) was added. The mixture reaction was stirred at reflux overnight. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL). And the organic layer was dried over Na2SO4. The product 3′-({[(1,1-dimethylethyl) (dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile (5.10 g, 60%) was purified by flash column chromatography. 1H NMR (400 MHz, CDCl3): delta 7.67 (t, J=5.2 Hz, 1H), 7.54-7.32 (m, 5H), 4.81 (s, 2H), 0.94 (s, 9H), 0.13 (s, 6H).

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US2009/197871; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 144649-99-0, name is 5-Bromo-2-methoxybenzonitrile, belongs to nitriles-buliding-blocks compound, 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 144649-99-0, category: nitriles-buliding-blocks

Preparation of Intermediate 1-2; 5-(2-Chloropyrimidin-4-yl)-2-methoxybenzonitrileReagents: (a) Pd(dppf)Cl2, KOAc, /?-dioxane: (b) 2,4-dichloropyrimidine, K2C03,Pd(PPh3)4, CH3CN, H20, reflux, 5 h;[0209] Step 1. 2-Methoxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile: To a solution of 2-methoxy-5-bromobenzonitrile (5.0 g, 23.6 mmol) in /?-dioxane (125 mL), bis(pinacolato)diborane (9.0 g, 35.4 mmol), KOAc (7.0 g, 71.3 mmol), and Pd(dppf)Cl2 (0.863 g, 1.17 mmol) were added. The resulting mixture was stirred for 18 h at 80 C. The cooled reaction crude was diluted with 120 mL EtOAc, washed with H20 and brine, dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by column chromatography on Si02 (Hexanes/EtOAc) to afford the title compound (5.6 g, 92%). GC/MS (EI, M+) 245

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MYREXIS, INC.; HOLCOMB, Ryan C.; SEBAHAR, Paul R.; SUZUKI, Kazuyuki; McLEOD, Donald A.; DASTRUP, David M.; HOARAU, Christophe; HALTER, Robert J.; BURSAVICH, Matthew Gregory; SHENDEROVICH, Mark D.; RICHARDS, Burt; BARTEL, Paul L.; WO2012/142329; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, 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. category: nitriles-buliding-blocks

A mixture of 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1 .5 g, 5.91 mmol), 3,5-bis(trifluoromethyl)phenylboronic acid (1.90 g, 7.38 mmol), Pd(PPh3)4 (0.341 g, 0.3 mmol) in toluene (70 ml) was degassed for about 1.5 hours with bubbling argon. Vacuum-oven-dried cesium carbonate (3.61 g, 1 1 .07 mmol) was added and the mixture was degassed for an additional 30 minutes and then heated to about 110 C for about about 64 hours. The resulting mixture was worked up with dichloromethane/brine, and the organic phase was collected and dried over MgS04. The crude mixture was purified twice by column chromatography on a silica gelcolumn using eluents of 0% to 3.5% ethyl acetate in hexanes, and then 5% to 30% dichloromethane in hexanes. The clean product fractions were dried by rotaryevaporation to yield Compound 21 (1.15 g, 51 % yield) as a clear crystalline solid.

The synthetic route of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts