Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 70484-02-5, name is 6-Bromonaphthalene-2,3-dicarbonitrile, 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 70484-02-5, COA of Formula: C12H5BrN2

A mixture of 6-Bromodicyanonaphthalene(3) (1.0 g, 3.9 mmol), methyl-p-hydroxybenzoate (4)(2.0g, 13.2 mmol) and 6 g of K2CO3 in dry DMF (60 mL) was heated at 130for 20 h. After cooling down, the mixture was poured into ice water and extracted with chloroform, and then was washed with water thoroughly. The organic phase was dried over anhydrous MgSO4and concentrated, which was chromatographed (silica gel) usingCHCl3/ethyl acetate (40:1) as the eluent to give 5 as a white solid (0.28 g, 22%). 1H NMR (300 MHz, CDCl3, 25C, TMS): (ppm): 3.94 (s, 3H, CH3), 7.14 (d, 2H, Ar-H, J = 8.7), 7.38 (d, 1H, Ar-H, J=2.4 Hz), 7.56 (dd, 1H, Ar-H, J1=2.4 Hz, J2=9.0 Hz), 8.0 (d, 1H,Ar-H, J=9.0 Hz),8.12 (d, 2H, Ar-H, J=8.7 Hz), 8.18 (s, 1H, Ar-H), 8.33 (s, 1H, Ar-H). 13C NMR(75MHz, CDCl3, 25C, TMS): (ppm): 52.25, 108.96, 111.14, 114.03, 115.69, 115.84, 119.39, 124.29, 126.87, 129.80, 131.09, 132.14, 134.67, 134.75, 135.57, 158.54, 159.15, 166.17. MS (ESI) m/z 329.09; (M+H+) (calculated for 329.32).

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:
Article; Luan, Liqiang; Ding, Lanlan; Zhang, Weijia; Shi, Jiawei; Yu, Xiaoqiang; Liu, Wei; Bioorganic and Medicinal Chemistry Letters; vol. 23; 13; (2013); p. 3775 – 3779;,
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Application of 191014-55-8,Some common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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.

(S)-4-bromo-2,3-dihydro-1H-inden-1-amine (1.0 g, 4.7 mmol), 4-fluoro-2-methoxybenzonitrile (0.89 g, 5.89 mmol), and N,N-Diisopropylethylamine (0.90 g, 7.1 mmol), were suspended in N-Methyl-2-pyrrolidone (5 mL). The suspension was stirred and heated to 115 C. for 48 h. The reaction was cooled to room temperature, and diluted with ethyl acetate and diethyl ether. The mixture was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The product was purified by column chromatography (ethyl acetate/hexanes) to provide (S)-4-((4-bromo-2,3-dihydro-1H-inden-1-yl)amino)-2-methoxybenzonitrile. (S)-4-((4-bromo-2,3-dihydro-1H-inden-1-yl)amino)-5-chloro-2-methoxybenzonitrile:

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Cho, Aesop; Graupe, Michael; Lad, Lateshkumar Thakorlal; Machicao Tello, Paulo A.; Medley, Jonathan William; Metobo, Samuel E.; Naduthambi, Devan; Phillips, Barton W.; Simonovich, Scott Preston; Wang, Peiyuan; Watkins, William J.; Xu, Jie; Yang, Kin Shing; Ziebenhaus, Christopher Allen; US2020/17471; (2020); A1;,
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Reference of 1217-45-4,Some common heterocyclic compound, 1217-45-4, name is 9,10-Anthracenedicarbonitrile, molecular formula is C16H8N2, 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 99 STR107 (+-)-Cis-3,4,9,9a-tetrahydroindeno[2,1-c]thiopyran-4a(1H)-amine To a solution of the benzylamine (1.0 g, 3.4 mmol) from Example 98 in acetonitrile/water (7:3) is added 9,10-dicyanoanthracene. The reaction is irradiated as described in Tetrahedron Letters 29, 4157 (1988). The reaction yields the primary amine which is converted to the title compound.

The synthetic route of 1217-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bigge; Christopher F.; Hays; Sheryl J.; Johnson; Graham; Novak; Perry M.; Ortwine; Daniel F.; US5071853; (1991); A;,
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Reference of 70484-02-5,Some common heterocyclic compound, 70484-02-5, name is 6-Bromonaphthalene-2,3-dicarbonitrile, molecular formula is C12H5BrN2, 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.

SYNTHESIS EXAMPLE 15 Synthesis of 6-cyclohexylthio-2,3-dicyanonaphthalene Ten grams (38.9 mmoles) of 6-bromo-2,3-dicyanonaphthalene and 14 g (77.9 mmoles) of copper cyclohexylthiolate STR135 were refluxed in a mixed solvent of 200 ml of quinoline and 55 ml of pyridine for 20 hours until the starting compounds had completely been consumed. After cooling, the reaction mixture was poured into 1/1 mixture of water and methanol, and the deposited precipitate was collected by filtration. After separating decomposed products and by-products present in the crystal thus obtained by silica gel column chromatography, it was recrystallized from toluene/hexane to obtain 7.33 g (63%) of a light yellow crystal. Referring to the following analyses, it was identified as 6-cyclohexylthio-2,3-dicyanonaphthalene.

The synthetic route of 70484-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hitachi, Ltd.; Hitachi Chemical Co., Ltd.; US5484685; (1996); A;,
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Synthetic Route of 133541-45-4, A common heterocyclic compound, 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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.

(0527) To a stirred suspension of (R)-4-phenyloxazolidin-2-one (100 mg, 0.613 mmol), 4- bromo-2,5-difluorobenzonitrile (134 mg, 0.613 mmol), copper(I) iodide (175 mg, 0.919 mmol), and potassium carbonate (254 mg, 1.84 mmol) in anhydrous 1,4-dioxane (3.0 mL) under an atmosphere of nitrogen was added (1S,2S)-(+)-N,N’-dimethylcyclohexane-1,2-diamine (0.29 mL, 1.8 mmol) and the resulting mixture was heated at 90 C for 20 h. After cooling to ambient temperature the mixture was filtered through a pad of Celite and the filtered solids were washed with ethyl acetate (30 mL). The combined filtrates were evaporated to dryness in vacuo and the crude residue was purified by flash silica gel chromatography (ISCO CombiFlash Rf Purification System; 12 g SepaFlash Silica Flash Column, eluting with a 0-50% ethyl acetate in hexanes gradient) to afford the title compound as an oil. MS (ESI) m/z [M+H+CH3CN]+: 342.2.

The synthetic route of 133541-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALJI, Abbas; BERGER, Richard; STUMP, Craig, A.; SCHLEGEL, Kelly Ann, S.; MULHEARN, James, J.; GRESHOCK, Thomas, J.; WANG, Deping; FRALEY, Mark, E.; JONES, Kristen, G.; (273 pag.)WO2017/222951; (2017); A1;,
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Related Products of 354814-19-0,Some common heterocyclic compound, 354814-19-0, name is 5-Amino-2-(trifluoromethyl)benzonitrile, molecular formula is C8H5F3N2, 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.

Intermediate 38: 2-{[3-Cyano-4-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate; Triethylamine (1.09 g, 10.8 mmol) was added to a stirred solution of 5-amino-2- (trifluoromethyl)benzonitrile (Intermediate 37, 1.0 g, 5.37 mmol) in DCM (40 mL), at 0C, and the mixture was stirred for 15 min. Chloro-2-oxoethyl acetate (1.10 g, 8.06 mmol) was added at 0C and the mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with DCM and washed with ice water, and saturated brine solution. The organic layer was dried over anhydrous Na2S04, and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-40% EtOAc/pet. ether to give the title compound (1.1 g).MS ES+ve m/z 285 (M-H).1H NMR (400 MHz, Chloroform-d) delta ppm 2.26 (s, 3 H), 4.76 (s, 2 H), 7.72-7.82 (m, 1 H), 7.90-8.00 (m, 1 H), 8.08-8.18 (m, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-2-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; CONVERGENCE PHARMACEUTICALS LIMITED; BESWICK, Paul John; GLEAVE, Robert James; HACHISU, Shuji; VILE, Sadie; BERTHELEME, Nicolas; WARD, Simon E; WO2012/4604; (2012); 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. 58949-75-0, name is 4-(2-Oxopropyl)benzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

EXAMPLE 47 2-[(Aminocarbonyl)amino]-4-methyl-5-(4-cyanophenyl)-3-thiophenecarboxamide Prepared by the method of Example 26 from (4-cyanophenyl)acetone. MS (ES) 299 (M-H)-.

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; Baxter, Andrew; Brough, Stephen; Faull, Alan; Johnstone, Craig; McInally, Thomas; US2002/107252; (2002); A1;,
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175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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. Recommanded Product: 175596-01-7

Step (ii) Raney nickel (2.0 g) was added to a solution of methyl 4-cyano-2-fluorobenzoate (obtained as described in step (i) above) (10.1 g, 61.6 mmol) in acetic acid (200 ml.) and water (100 niL). The mixture was stirred at RT under argon at 20 bar. After 18 h the mixture was filtered through diatomaceous earth, washing through with water (1000 mL). The filtrate was extracted with EtOAc (3 chi 300 mL). The combined organic phases were dried and concentrated, adding toluene to assist removal of acetic acid, to give methyl 2- 11 uoro-4-( hydroxy meth) l)benzoate (crude, 6.06 g) which was used in the next step without further purification or characterisation.

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LIMITED; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; WO2015/25164; (2015); A1;,
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Related Products of 191014-55-8, 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. 191014-55-8 name is 4-Fluoro-2-methoxybenzonitrile, 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.

A solution of (S)-3-(l-aminoethyl)-6-chloroquinolin-2(lH)-one hydrochloride II-l (201 mg, 0.776 mmol) and 4-fluoro-2-methoxybenzonitrile (236 mg, 1.56 mmol) in DMSO (5 ml) was treated with DIEA (400 mu, 2.29 mmol) and stirred at 110 C for three days. The sample was diluted with water (75 mL) and extracted with DCM (2×50 mL), dried, and filtered. Silica gel was added, and the solvent was evaporated under reduced pressure. The material was chromatographed by Biotage MPLC (silica gel, 0 to 70% EtOAc in hexanes, with isocratic elution when peaks came off) to provide a gum. The material was dissolved in DCM (10 mL), washed with water (2×10 mL), dried (Na2S04), filtered, and evaporated to provide 76 mg yellow powder. The sample was mixed with MeCN (4 mL) and water (2 mL), frozen on a dry ice/acetone bath, and lyopholyzed to provide the title compound 1-2 (71.1 mg, 0.193 mmol, 24.93 % yield, HPLC purity 96.3% at 220 nm) as a solid. 1H NMR (300 MHz, DMSO-d6): delta ppm 12.07 (s, 1 H), 7.77 (d, J=2.35 Hz, 1 H), 7.74 (s, 1 H), 7.50 (dd, J=8.65, 1.91 Hz, 1 H), 7.35 – 7.20 (m, 3 H), 6.27 (s, 1 H), 6.06 (d, J=7.90 Hz, 1 H), 4.79 – 4.65 (m, 1 H), 3.75 (s, 3 H), 1.43 (d, J=6.45 Hz, 3 H). LCMS (Method 1): Rt 2.37 min., m/z 354.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-2-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
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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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H2ClF4N

(c) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-4-pentafluoroethylpyrimidin-6-one (compound No 4 in Table I) was prepared by the reaction of 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene and 4-pentafluoroethylpyrimidin-6-one. 1 H NMR delta(CDCl3 /d6 -DMS0): 8.15 (1H,s); 8.09 (2H,m); 7.09 (1H,s).

The synthetic route of 129931-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
Nitrile – Wikipedia,
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