Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 127667-01-0, name is 2-Fluoro-5-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 127667-01-0, name: 2-Fluoro-5-methoxybenzonitrile

11 g of 2-fluoro-5-methoxybenzonitrile was added to a mixed solvent of 200 ml of methanol and 100 ml of water, and 9 g of hydroxylamine hydrochloride and 12 g of anhydrous sodium acetate were added. The reaction was heated under reflux for 12 hours, and water and ethyl acetate were added thereto. The solution was separated by extraction, and the organic layer was collected, dried and concentrated. The residue was separated on a silica gel column to obtain 9 g of 2-fluoro-N’-hydroxy-5-methoxybenzylhydrazone.

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, 2-Fluoro-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (6 pag.)CN107698535; (2018); A;,
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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. 2042-37-7, name is 2-Bromobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H4BrN

General procedure: activityThe catalytic activities of the prepared catalysts were testedfor the Suzuki-Miyuara cross-coupling reaction of phenylboronicacid with various bromoarenes. In a typical experiment, 0.70 mmolof the aryl bromide, 1.5 molar equivalents of phenylboronic acidand 1.5 molar equivalents of base, respectively, and 1.3 mmol ofanisole (internal standard) were dissolved in 20 ml of solvent. 5 mgof the catalyst (corresponding to approximately 0.05 mol% palla-dium) were added. The reaction was carried out under stirring at 75C. To monitor the reaction progress, samples from the reac-tion solution (100 l) were taken after 15, 30, 60, 90 and 120 min.HPLC sample solutions were prepared by dissolving 100 l of thereaction solution in 1 ml of the initial mobile phase. HPLC analy-sis was done using an Agilent 1100 series HPLC system (Agilent,Waldbronn, Germany), equipped with an online degasser, qua-ternary pump, autosampler, thermostatted column compartmentand UV-vis diode array detector. An Agilent Poroshell 120 EC-C18 reversed-phase column (50 × 4.6 mm; 2.7 m) was used asstationary phase. Analysis was carried out under gradient elu-tion conditions using a mobile phase consisting of methanol andaqueous phosphoric acid (water: phosphoric acid = 300:1 v/v). Col-umn temperature was set to 25C. UV-detection was performed atwavelengths of 237 and 270 nm over a run time of 15 min.

The synthetic route of 2042-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lichtenegger; Maier; Hackl; Khinast; Goessler; Griesser; Kumar, V.S. Phani; Gruber-Woelfler; Deshpande; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 39 – 51;,
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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. 64248-62-0, name is 3,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3F2N

Potassium carbonate (19.9 g, 144 mmol) was added to a mixture of 3,4-difluorobenzonitrile (10.0 g, 71.9 mmol) and 4-hydroxybenzaldehyde (8.78 g, 71.9 mmol) in N,N-dimethylformamide (200 mL). The reaction mixture was heated to 100 C. for 4 hours, whereupon it was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was washed with water (3×200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo, affording the product as a yellow solid (17.7 g). By 1H NMR, this material contained some N,N-dimethylformamide. Yield, corrected for N,N-dimethylformamide: 16.8 g, 69.6 mmol, 97%. 1H NMR (400 MHz, CDCl3) delta 9.99 (s, 1H), 7.93 (br d, J=8.6 Hz, 2H), 7.58-7.48 (m, 2H), 7.21 (dd, J=8.4, 8.0 Hz, 1H), 7.14 (br d, J=8.6 Hz, 2H).

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 64248-62-0.

Reference:
Patent; Pfizer Inc.; Kablaoui, Natasha Mariam; Green, Michael Eric; Montgomery, Justin Ian; Brodney, Michael Aaron; Verhoest, Patrick Robert; Kauffman, Gregory Wayne; Rankic, Danica Antonia; Mente, Scot Richard; Rogers, Bruce Nelsen; Arora, Kapildev Kashmirilal; Dunn, Matthew Francis; (98 pag.)US2018/148432; (2018); A1;,
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Related Products of 34403-48-0, A common heterocyclic compound, 34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, molecular formula is C9H10N2, 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.

A round-bottom flask was charged with norbornane-2-carboxylic acid (1.0 g, 1 eq.) and thionyl chloride (O.95 g, 2 eq.) was added dropwise. The mixture was warmed to 70 C. for 1 hour. The mixture was cooled to room temperature and dichloromethane (20 mL) was added. Subsequently 4-(methylaminomethyl)benzonitrile (1.03 g, 1.1 eq) was added portion wise. The mixture was stirred at room temperature over night until HPLC indicated complete conversion. The organic layers were washed with hydrochloric acid (1 M), brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the title compound was used directly without further purification.

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; TERTERYAN-SEISER, Violeta; GRAMMENOS, Wassilios; QUINTERO PALOMAR, Maria Angelica; CRAIG, Ian Robert; WIEBE, Christine; MENTZEL, Tobias; FEHR, Marcus; ESCRIBANO CUESTA, Ana; WINTER, Christian Harald; LOHMANN, Jan Klaas; MUELLER, Bernd; CAMBEIS, Erica; GROTE, Thomas; SEET, Michael; (36 pag.)US2020/45974; (2020); A1;,
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Electric Literature of 1897-52-5, These common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, 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.

Step 3 : 2-Fluoro-6- [1 -(2-fluorophenyl)piperidin-4- ylmethoxy]benzonitrile-(Method C).To a cold (ice water) suspension of sodium hydride (0.044 g, 1.1 mmol) in anhydrous DMF (1 mL) is added a solution of l-(2-fluorophenyl)piperidin-4-yl]methanol (0.19 g, 0.91 mmol) in anhydrous DMF (2 mL) over 11 minutes. After allowing to room temperature over 2 hours, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (0.14 g, 1.0 mmol) in anhydrous DMF (1 mL), and allowed to room temperature over 18 hours. The reaction mixture is poured into ice water with vigorous stirring and the resulting solid is filtered, washed with water, and dried under vacuum 1.5 hours to give 2-luoro-6-[l-(2-fluorophenyl)piperidin-4-yloxy]benzonitrile (0.19O g, 63% yield).

The synthetic route of 1897-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; deCODE Chemistry, Inc.; WO2008/16973; (2008); A1;,
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Reference of 218632-01-0,Some common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.

tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58). Sodium hydride (88 mg, 95%) was added, under argon flush, to a solution of tert-butyl 9-(2,6-difluorobenzyl)-2-amino-8-oxo-8,9-dihydropurine-7-carboxylate (57) (191 mg) and 3-fluoro-4-nitrobenzonitrile (415 mg) in DMF (5 mL) at -40 C. The reaction mixture was allowed to warm to -20 C. over 3 hr then quenched by the addition of sat. aq. NH4Cl, once at RT the mixture was diluted with EtOAc and separated. The organics were washed with brine (3*), dried, filtered and evaporated, purified via column chromatography, (eluted with DCM and 1 and 2.5% MeOH/DCM) to yield tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58) (288 mg), MH+=524. tert-Butyl 9-(2,6-difluorobenzyl)-2-(6-cyano-1H-benzo[d]imidazol-1-yl)-8-oxo-8,9-dihydropurine-7-carboxylate (60).

The synthetic route of 218632-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; US2008/119496; (2008); A1;,
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Related Products of 24056-34-6, A common heterocyclic compound, 24056-34-6, name is 4-Hydroxycyclohexanecarbonitrile, molecular formula is C7H11NO, 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 4-hydroxycyclohexane-l-carbonitrile (1.5 g, 12 mmol) and pyridine (1.16mL, 14.4 mmol) in DCM (30 mL) was added triflic anhydride (2.7 mL, 14.4 mmol) at about -20 C. The solution was then kept at -5 to 0 C by an ice-salt bath. After lhr, the mixture was diluted with hexane (double the volume of DCM) and filtered through a pad of Celite. The solvent was evaporated to afford the crude triflates that were used directly for the coupling reaction

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:
Patent; GENENTECH, INC.; NEWLINK GENETICS CORPORATION; PEI, Zhonghua; PARR, Brendan; LIU, Wendy; PASTOR, Richard; GAZZARD, Lewis; JAIPURI, Firoz; KUMAR, Sanjeev; POTTURI, Hima; WU, Guosheng; LIN, Xingyu; CHU, Yanyan; YUEN, Po-wai; (149 pag.)WO2019/6047; (2019); A1;,
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Electric Literature of 628-20-6, 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 628-20-6 as follows.

EXAMPLE 27 5-(3-CHLOROPROPYL)TETRAZOLE A mixture of 4-chlorobutyronitrile, (0.05 mol) sodium azide (0.20 mol) and anhydrous aluminum chloride (0.05 mol) in 100 ml of dry tetrahydrofuran is refluxed for 24 hours. After cooling to ambient temperature the reaction is acidified with 75 ml of 15% hydrochloric acid while the hydrazoic acid generated is removed by means of an aspirator. The organic and aqueous layers are then separated and the aqueous layer extracted with ethylacetate. The combined organic extracts are dried (magnesium sulfate) and evaporated to give 5-(3-chloropropyl)tetrazole which is used directly in the next step.

According to the analysis of related databases, 628-20-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rhone-Poulenc Rorer Pharmaceuticals Inc.; US5166210; (1992); A;,
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Application of 50594-78-0, 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. 50594-78-0 name is 5-Fluoro-2-nitrobenzonitrile, This 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.

Tert-butyl [1-(4-amino-3-cyanophenyl)pyrrolidin-3-yl]methylcarbamate 2-Cyano-4-fluoro-1-nitrobenzene was treated with tert-butyl methylpyrrolidin-3-yl-carbamate and subsequently reduced by method C-a. This resulted in the product with the molecular weight of 316.41 (C17H24N4O2); MS (ESI): 317 (M+H+).

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

Reference:
Patent; Aventis Pharma Deutschland GmbH; US2004/220191; (2004); A1;,
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Application of 64248-64-2, These common heterocyclic compound, 64248-64-2, name is 2,5-Difluorobenzonitrile, 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.

Added in the reaction bottle 20g of the 2,5-dichlorobenzonitrile, 12g dry potassium fluoride, used for dissolving sulfolane 34ml 0.55mol/L. Stir until no solid particles. After mixing, heating to 170 C, in 170 C maintain the temperature of 2 hours. Then continue to heating to 210 C, is kept at this temperature for 4 hours, to stop the reaction, the reaction bottle to add new 18mL0.55mol/L sulfolane, the temperature rising to 120 C inject the ammonia 2 hours, the reaction bottle cooling to 30 C, slowly dropping 24mL0.66moL/L sodium nitrite aqueous solution. After the reaction is complete 10g acrylonitrile, heating to 110 C. To fully dissolve the 15g copper powder and 20 ml/L the hydrobromidum, heating to 150 C, maintain 2 hours, to stop the reaction. Dilution with water extraction with ethyl acetate, to obtain in the dilute 40ml0.98mol/L in aqueous solution of sulfuric acid, heating to 110 C hydrolysis 8 hours, cooling to room temperature after the reaction, by adding 400 ml distilled water, once again extracted with ethyl acetate to obtain 15.28g 2-fluoro-5-bromonicotinic acid, to yield 80.12%.

The synthetic route of 64248-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changzhou University; Dong, YanMin; (5 pag.)CN104387264; (2016); B;,
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