Author: Jessica.F

Application of 86770-80-1, 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. 86770-80-1, name is 3,3-Difluorocyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3 ,3-difluoro- 1 -(4-(trifluoromethyl)pyridin-2-yl)cyclobutanecarbonitrile [1270] Example 125B and 2-fluoro-4-(trifluoromethyl)pyridine (0.900 mL, 7.39 mmol) were dissolved in toluene (2.4 mL), cooled to <5 C and added KHMDS (29.6 mL, 14.78 mmol) dropwise, allowed to warm slowly to room temperature and stirred for 90 minutes. The mixture was diluted with MTBE and washed with water (2x). The organic phase was dried (Na2S04), filtered, and concentrated. The residue was chromatographed on silica gel (0-25% EtOAc/hexanes) to provide Example 125C (1.22 g, 4.65 mmol, 63.0 % yield). XH NMR (300 MHz, DMSO-d6) ? 9.00 - 8.94 (m, 1H), 8.04 - 7.99 (m, 1H), 7.88 (ddd, J= 5.1, 1.6, 0.8 Hz, 1H), 3.68 - 3.48 (m, 5H). 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, 3,3-Difluorocyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
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Electric Literature of 493038-93-0, These common heterocyclic compound, 493038-93-0, name is 2-(3-Chloro-5-fluorophenyl)acetonitrile, 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.

General procedure: A mixture of (3-(trifluoromethyl)phenyl)acetonitrile (45.2 g,244 mmol) and diethyl dithiophosphate (50.0 g, 269 mmol) in 4 N HCl solution in EtOAc (500 mL, 2000 mmol) was stirred at room temperature overnight. The mixture was washed with water, 1 N aqueous NaOH solution, and brine, dried over Na2SO4, and concentrated in vacuo. The residue was triturated with hexane with ice-bath cooling. The precipitate was collected by filtration followed by washing with hexane to give 35.0 g (65%) of 6a as colorless solid.

Statistics shows that 2-(3-Chloro-5-fluorophenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 493038-93-0.

Reference:
Article; Tokumaru, Kazuyuki; Ito, Yoshiteru; Nomura, Izumi; Nakahata, Takashi; Shimizu, Yuji; Kurimoto, Emi; Aoyama, Kazunobu; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry; vol. 25; 12; (2017); p. 3098 – 3115;,
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Adding a certain compound to certain chemical reactions, such as: 191014-55-8, name is 4-Fluoro-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 191014-55-8, category: nitriles-buliding-blocks

To a mixture of intermediate 127, 4-fluoro-2-methoxybenzonitrile, (800 mg, 5.3 mmol) and conc.HCl (0.53 mL, 6.36 mmol, 1.2 eq.) in ethanol (20 mL) was added 10% Pd-C (100 mg; Aldrich), and the mixture hydrogenated at 1 atm hydrogen for 15 hrs at room temperature. To this mixture was added an additional amount of conc.HCl (1 mL) and 10% Pd-C (200 mg) and the reaction allowed to continue for another 40 hrs. The mixture was filtered through Celite and the filtrate concentrated in vacuo to dryness. The residue was triturated with ether to provide the title compound (895 mg, Yield 88%) as a white powder: 1H NMR (CDCl3, 500 MHz) ? ppm: 3.84 (3H, s, OMe), 3.91 (2H, d, J=5.5 Hz, N-CH2), 6.81 (1H, dt, J=2.5 Hz, J=J=8.5 Hz, Ar-H), 6.99 (1H, dd, J=2.5 Hz, J=11.3 Hz, Ar-H), 7.47 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H); 3C NMR (CDCl3, 125.8 Hz) ? ppm: 36.76, 56.03, 99.30, 99.51 106.28, 106.45, 117.93, 117.95, 131.60, 131.69, 158.56, 158.64, 162.28, 164.22. HRMS (ESI) calcd for C8H11FNO (M+H) 156.0825, found 156.0830.

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; 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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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 24056-34-6 as follows. SDS of cas: 24056-34-6

6.4 g (51.1 mmol) of 4-hydroxy-cyclohexanecarbonitrile (121) were dissolved in 120 ml_ of dichloromethane, cooled to 0 0C and 14.9 nriL (13.7 g, 128 mmol) of 2,6-lutidine and 15.4 ml_ (14.9 g, 56.2 mmol) of tert-butyldimethylsilyltrifluoromethanesulfonate were added. The reaction mixture was stirred for 16h at room temperature, then additional 5.0 ml_ of tert-butyldimethylsilyltrifluoromethanesulfonate were added and stirring continued for 1 h. The reaction mixture was diluted with 100 ml_ of dichloromethane and washed with 100 ml_ of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine. The organic phase was dried over magnesium sulphate, filtered, concentrated in vacuo and purified by silica gel chromatography (heptanes:ethyl acetate) to give 9.76 g of the desired product. Rt = 0.95 min (Method 18). Detected mass: 240.1 (M+H+).

According to the analysis of related databases, 24056-34-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; WO2009/156100; (2009); A1;,
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Reference of 39786-34-0, 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. 39786-34-0, name is Ethyl 2-(2-cyanophenoxy)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 2000-mL round-bottom flask was placed a solution of KOtBu (18 g,160.41 mmol) in THF (600 mL) then a THF solution (400 mL) solution of ethyl 2-(2-cyanophenoxy)acetate (20 g,97.46 mmol,as prepared in the previous step) was added dropwise with stirring. After completion of addition,the reaction wasstirred at rt for 2 h,quenched by the addition of water,and extracted with EtOAc (3×200 mL).The organic extracts were combined,washed with brine (2×200 mL),dried over anhydrousNa2SO4,and concentrated under reduced pressure affording 17 g of the title compound as ayellow solid. Mass Spectrum (LCMS,ESI pos): Calcd. for C,,H,2NO3: 206.1 (M+H); Found:206.1.

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, Ethyl 2-(2-cyanophenoxy)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
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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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