Tag: M.W=200-300

Reference of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-oxazolidone (0.390 g, 4.50 mmol), K2CO3 (0.970 g, 7.0 mmol) and xantphos (0.231 g, 0.40 mmol) in dioxane (10 mL) was degassed with argon for 15 min. Pd2 dba3 (0.140 g, 0.15 mmol) was introduced and then the reaction mixture was heated at 70 C. for 18 h. The mixture was cooled, diluted with dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes:ethyl acetate (1:1) to (3:7) gradient as the eluent to afford the title compound as a white solid (0.460 g, 50% yield): 1H NMR (400 MHz, CDCl3) ? ppm: 7.73 (1H, dd, J=5.8, 8.6 Hz), 7.43 (1H, dd, J=2.5, 9.6 Hz), 7.11 (1H, ddd, J=2.5, 7.5, 8.7 Hz), 4.60 (2H, t, J=7.1 Hz), 4.29 (2H, t, J=7.1 HJz); LCMS (+ESI, M+H+) m/z 207.

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

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
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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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluorophenylacetonitrile

To a solution of compound A26-3 (9.6 g, 45 mmol) in THF (100 ml) under N2 at room temperature was added LDA (2M inTHF, 56 ml) over 1 h. Then the mixture was treated with iodomethane (22. 3g, 157.5 mmol). The mixture was then quenched by adding H20 (50 mL) and extracted with EtOAc (100 mL) three times. The combined organic layers were washed with brine, dried over Na2504, and concentrated in vacuo to provide a residue, which was purified by chromatography over silica gel (eluting with PE: EA=10: 1) to give compound A26-4.

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BIFU, Tesfaye; BIJU, Purakkattle; BLIZZARD, Timothy A.; CHEN, Zhengxia; CLEMENTS, Matthew J.; CUI, Mingxiang; FRIE, Jessica L.; HAGMANN, William K.; HU, Bin; JOSIEN, Hubert; NAIR, Anilkumar G.; PLUMMER, Christopher W.; WO2015/176267; (2015); A1;,
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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. 85068-32-2, name is 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, A new synthetic method of this compound is introduced below., Safety of 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile

General procedure: Absolute ethyl alcohol (100 mL), substituted benzylcyanide (5.4 mmol), and 2,3,4-trimethoxybenzaldehyde (5.4 mmol) were added to three-necked reaction flask with a mechanical stirrer. The reaction mixture was stirred for 0.5 h at 70 C. Then, a sodium hydroxide (20 %) solution was added dropwise until a precipitate formed. The reaction was cooled to room temperature and the mixture was poured into ice-water. The residue was filtered and washed with hot water to pH 7. The crude product was dried under vacuum and then recrystallized in ethanol

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; Oezen, Furkan; Tekin, Suat; Koran, Kenan; Sandal, Sueleyman; Goerguelue, Ahmet Orhan; Research on Chemical Intermediates; vol. 42; 12; (2016); p. 7793 – 7805;,
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Related Products of 79463-77-7, A common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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.

Compound 42 (424 mg, 1.78 mmol) in 2-propanol (40 mL) was treated with adamantane-1-methylamine hydrochloride (23)18 (357 mg, 1.77 mmol) and triethylamine (300 muL, 2.16 mmol) and the homogeneous solution was stirred at room temperature for 18 h. The resulting precipitate was collected by filtration, washed with diethyl ether (10 mL) and dried under vacuum to give 52 as a white solid (275 mg, 50%). Data matched that previously reported.18

The synthetic route of 79463-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Callis, Timothy B.; Reekie, Tristan A.; O’Brien-Brown, James; Wong, Erick C.N.; Werry, Eryn L.; Elias, Nabiha; Jorgensen, William T.; Tsanaktsidis, John; Rendina, Louis M.; Kassiou, Michael; Tetrahedron; vol. 74; 12; (2018); p. 1207 – 1219;,
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Related Products of 70484-01-4, 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. 70484-01-4, name is 4-Bromophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Compound B-3 (8.4 mmol) and Compound E-4 (2.8 mmol) were reacted in the presence of DBU (11.2 mmol)And reacted under n-pentanol reflux conditions to obtain compound F-1 (0.28 mmol, 10%).To compound F-1 (0.28 mmol) in DMF,Zinc acetate was added and the mixture was stirred at 80 C. for 2 hours to obtain F-2 (0.25 mmol, 90%).F-2 (0.25 mmol) was dissolved in dichlorobis (triphenylphosphine) palladium (II) (PdCl 2 (PPh 3) 2)After cross coupling with triisopropylsilylacetylene in the presence of copper iodide,Treated with tetra-n-butylammonium fluoride (TBAF)Compound F-3 (0.19 mmol, 76%) was obtained.Compound F-3 (0.19 mmol) was cross-coupled with 4-iodobenzoic acid to obtain phthalocyanine dye D-2 (0.11 mmol, 58%).

The chemical industry reduces the impact on the environment during synthesis 4-Bromophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NIPPON STEEL & SUMIKIN CHEMICAL COMPANY LIMITED; KYUSHU INSTITUTE OF TECHNOLOGY; HAYASE, SHUZI; PANDEY, SHYAM SUDHIR; YAMAGUCHI, YOSHIHIRO; OCHI, NORIAKI; FUJINO, KENICHI; OKAMOTO, ETSUYA; KOMAYA, YOHEI; (25 pag.)JP5906522; (2016); B2;,
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Adding a certain compound to certain chemical reactions, such as: 70484-01-4, name is 4-Bromophthalonitrile, 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 70484-01-4, Quality Control of 4-Bromophthalonitrile

A stirrer,thermometer,condenser,A 100 mL four-necked glass flask equipped with a glass stopper was purged with nitrogen,The open end of the condenser was sealed with a gentle stream of nitrogen. Palladium acetate (1.1 mg, 0.005 mmol),2-dicyclohexylphosphino-2 ‘, 6’-dimethoxybiphenyl (4.1 mg, 0.01 mmol),4-bromophthalonitrile (104 mg, 0.5 mmol),4,4,5,5-tetramethyl-2- [p- (1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl) phenyl] -1,3- – borolane (255 mg, 0.6 mmol),And 1,4-dioxane (2 mL) were charged in a flask,The solid was dissolved by stirring at room temperature for 30 minutes. Cesium carbonate (326 mg, 1.0 mmol)Was added and the mixture was stirred at 25-29 C. for 12 days. Production of the target compound was confirmed by GC-MS of the reaction mixture.5 mL of toluene and 5 mL of water were added in order to the reaction mixture, and the mixture was stirred at room temperature for 5 minutes, then separated, and the organic layer was concentrated under reduced pressure.The residue was dissolved in toluene, filtered through 10 g of activated alumina, and the obtained crude product was purified by preparative GPC to obtain 142 mg of the objective compound as a white solid.

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.

Reference:
Patent; SHIN-ETSU CHEMICAL COMPANY LIMITED; KIYOMORI, AYUMU; ITOH, YUSUKE; (49 pag.)JP2015/10084; (2015); A;,
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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. 62088-13-5, name is Ethyl 3-(3-cyanophenyl)-3-oxopropanoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 62088-13-5

Part A: Preparation of ethyl 5-(3-cyanophenyl)-1-methyl-1H-pyrazole-4-carboxylate A mixture of ethyl-3-cyanobenzoylacetate (1.0 G, 5 mmol) and N,N-dimethylformamide dimethylacetal (2.74 G, 14 mmol) was heated to 100 C. for 24 h. The reaction mixture was concentrated in vacuo and the residue was re-dissolved in methanol (5 Ml), followed by addition of methyl hydrazine (0.3 Ml, 6 mmol). The reaction mixture was stirred at room temperature for 2 h and then concentrated in vaccuo. The residue was partitioned between ethyl acetate-water (60 Ml, 4:1), washed with water, dried over Na2SO4 and concentrated. The crude was purified using silica gel column chromatography (1 to 15% ethyl acetate-dichloromethane) to yield 0.36 G of required regioisomer; ethyl 5-(3-cyanophenyl)-1-methyl-1H-pyrazole-4-carboxylate and 0.3 G of ethyl 3-(3-cyanophenyl)-1-methyl-1H-pyrazole-4-carboxylate. MS m/z 256.3(M+H)

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 62088-13-5.

Reference:
Patent; Purandare, Ashok Vinayak; Chen, Zhong; US2007/60589; (2007); A1;,
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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 120315-65-3 as follows. Recommanded Product: 120315-65-3

Preparation 42 tert-butyl 2-(4-cyano-2 methoxyphenyl)acetate [0219] Combined (2-(tert-butoxy)-2-oxoethyl)zinc(II) chloride (4.24 mL, 2.122 mmol) and 4-bromo-3-methoxybenzonitrile (0.30g, 1.42 mmol) in THF (4.29 mL), then 2′- (dicyclohexylphosphino)-N,N-dimethyl-[l, l’-biphenyl]-2-amine (0.056 g, 0.141 mmol) and Pd(dba)2 (0.041 g, 0.071 mmol) were added and the reaction was refluxed at 100C overnight. The reaction mixture was concentrated down by rotary evaporation and purified on a silica gel column eluting with hexanes and EtOAc to give the title compound as a yellow oil (102 mg, 29%). MS m/z [M+H]+ 248.

According to the analysis of related databases, 120315-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
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1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8F4N2

First raw material 4,5-bis (pentafluorophenyl) -3,6-difluoro-phthalonitrile were prepared as follows: A 200ml reaction vessel equipped with a dropping funnel and a thermometer tetrafluorophthalonitrile 20.1 g ( 100.45mmol), potassium fluoride 13.99g (240.79mmol), was added to the methyl isobutyl ketone 130ml.After cooling with an ice-bath, conducted from the dropping funnel, was added slowly a solution of pentafluorophenol 37.0g (201.02mmol) of methyl isobutyl ketone 70 ml, then the reaction was stirred for 2 days at room temperature It was.Except inorganic salt and the reaction solution was filtered, washed with water using a separatory funnel, was dehydrated with anhydrous sodium sulfate, the reaction solution was concentrated in an evaporator.The concentrate, by re-precipitation purification with toluene / hexane solvent, 4,5-bis (pentafluorophenyl) -3,6-difluoro phthalonitrile, 70.83percent yield (37.4g, 70.81mmol obtained in).

The synthetic route of 1835-65-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ehime University; Nippon Shokubai Co.,Ltd.; Uno, Hidemitsu; Masuda, Tsuyoshi; (27 pag.)JP5656235; (2015); B2;,
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Synthetic Route of 425379-16-4, 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 425379-16-4 as follows.

2-Bromo-3-fluorobenzonitrile (1 .0 g, 5.0 mmol) and (1 H-pyrazol-5-yl)boronic acid (647 mg, 4.6 mmol) were combined and dissolved in degassed DME (15 ml_) then treated with NaHCO3 (1260 mg, 8.4 mmol) in water and the reaction purged with bubbling N2 for 5 minutes. The reaction was treated with Pd(PPh3) (288 mg, 0.2 mmol) and then purged with bubbling for 5 minutes in a sealed vessel and then heated to reflux for 2 h. Cooled to 23 C filtered and solid rinsed with EtOAc and the layers separated. The organic layers were combined, dried and concentrated under reduced pressure.Chromatography (0-30% ethyl acatate / hexanes) afforded 3-fluoro-2-(1 H- pyrazol-5-yl)benzonitrile (178 mg,19%).

According to the analysis of related databases, 425379-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
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