Tag: M.W=200-300

Synthetic Route of 1813-33-8, A common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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Application of 52805-37-5, A common heterocyclic compound, 52805-37-5, name is 3-(Benzyloxy)-4-methoxybenzonitrile, molecular formula is C15H13NO2, 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 11Preparation of 5-(benzyloxy)-4-m ethoxy-2-n itrobenzonitri le (IV)[0042] Under N2 (g), HNO3 (65%, 84 mL) was cooled to 0-5C. To a solution of 3-(benzyloxy)-4-methoxybenzonitrile (III, 14.0 g, 58.6 mmol, 1.0 eq.) in acetic acid (33.6 mL, 2.4 P) was added dropwise at 0-10C and after the addition the temperature was allowed to warm to 20-25 C. After the reaction completion, ice-water (150 mL, 10.7 P) was added to the mixture. The mixture was filtered, washed with water (30 mL x2) and dried in vacuo at 50C to give desired 5-(benzyloxy)-4-methoxy-2-nitrobenzonitrile (IV, 13.5 g) in 85% yield.1H NMR (400 MHz, CDCI3) O 7.80 (5, 1 H), 7.43-7.37 (m, 5H), 7.24(s, 1 H), 5.25(s, 2H),4.03 (5, 3H).l3 NMR (100MHz, CDCI3) O 152.70, 152.50, 142.91, 134.45, 129.00 (2C), 128.88,127.47 (2C), 117.13, 115.50, 108.17, 100.65, 56.85.

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; SCINOPHARM (CHANGSHU) PHARMACEUTICALS, LTD.; ZHANG, Xiaoheng; LV, Xizhou; WO2015/188318; (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. 1223434-15-8, name is Methyl 4-bromo-2-cyanobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-bromo-2-cyanobenzoate

Into a 100-mE 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 4-bromo-2-cyanobenzoate (2.0 g, 8.33 mmol, 1.00 equiv), ether (40 mE), 2-(propan-2-yloxy)propane propan-2-ol propan-2-yltitanium dihydrate (2.75 mE, 1.10 equiv). This was followed by the addition of EtMgl3r (3M) (5.5 mE, 2.00 equiv) dropwise with stirring at 0 C. The resulting solution was stirred for 3 hour at room temperature. The reaction was then quenched by the addition of 20 mE of hydrogen chloride (1M). The resulting solution was extracted with ethyl acetate (50 mEx2) and the organic layers combined and dried over anhydrous sodium sulfate. The residue was applied onto a silica gel colunm with ethyl acetate/petroleum ether (7/3). This resulted in 409mg (2 1%) of 6?-bromospiro[cyclopropane- 1,1 ?-isoindolin] -3-one as a yellow solid. EC-MS (ESj: mlz 238.00, 240.00 [MH], tR=0.79 mm, (1.90 minute run).

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; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Dong, Hanqing; Homberger, Keith R.; Qian, Yimin; Snyder, Lawrence B.; Wang, Jing; Zimmermann, Kurt; (504 pag.)US2018/215731; (2018); 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. 61150-58-1, name is 2-(2-Bromo-4-fluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 61150-58-1

Add potassium hydroxide (8.39 g, 150 mmol) and tetrabutylamine bromide(0.3 g, catalytic) to a solution of 2-(2-bromo-4-fluorophenyl)acetonitrile (4 g, 18.69 mmol) and 1,3-dibromopropane (4.15 g, 20.5 mmol) in toluene (20 mL). Stir it at 100 0C temperature for 2 h. Dilute the mixture with water and extract with ethyl acetate. Wash the organic layer with 1 N HCl and aqueous saturated sodium chloride. Dry over magnesium sulfate. Remove the organic solvent to give the crude product.Distill to give l-(2-bromo-4-fluorophenyl)cyclobutanecarbonitrile (boiling point 110- 120 C/0.3 Torr.) (1.5 g, 31 %). MS (GC) m/z 253 [M]+.Add 6 mL of HCl saturated methanol to the above solid and stir overnight. Evaporate the solvent to dry. Add NaHCO3 (1 M, 30 mL) and ether (20 mL). Stir for 15 min. Separate the organic layer and extract the aqueous layer with ether. Combine the ether solution and remove the solvent. Dissolve the residue in methanol (10 mL) and KOH (1.5 g) and stir over the weekend. Remove methanol and add water (30 mL). Extract with ethyl acetate and then acidify the aqueous layer with HCl. Extract the acidic solution with ethyl acetate, dry over MgSO4, and remove the solvent to give the title compound (1.0 g, 24 %). MS (ES) m/z 271 [M-I]”.

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; ELI LILLY AND COMPANY; WO2008/144223; (2008); A2;,
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Electric Literature of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-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.

5-Bromo-2-(2,2-dimethyl-butoxy)benzonitrile; Sodium hydride (60% oily) (2.0 g, 50.0 mmol) was gradually added to a solution of 5-bromo-2-fluorobenzonitrile (5.0 g, 25.0 mmol) and 2,2-dimethylbutan-1-ol (5.1 g, 50.0 mmol) in anhydrous DMF (100 mL) at 0C. After stirring at room temperature for 15 hours, the reaction mixture was poured into ice water followed by extracting with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried. The residue prepared by evaporation of the solvent was purified by silica gel column chromatography (hexane/ethyl acetate = 50/1) to give the title compound (6.2 g, 88%) as an oily product.

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

Reference:
Patent; Nippon Zoki Pharmaceutical Co., Ltd.; EP2128136; (2009); A1;,
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Electric Literature of 57418-97-0, 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. 57418-97-0 name is 4-Bromo-3-chlorobenzonitrile, 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.

3-chloro-4-bromobenzonitrile (300 mg, 1.39 mmol, 1.0 equiv), o-tolylboronic acid(189 mg, 1.39 mmol, 1.0 equiv), Pd(PPh3)4 (80 mg, 0.07 mmol, 0.05 equiv) and K2CO3 (383 mg, 2.77 mmol, 2.0 equiv) were weighed into a microwave tube and solvated with DME (3.0 mL) and H2O (1.0 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 minutes and then heated to 100 C under microwave irradiation for 2 hours. The reaction was allowed to cool to room temperature, filtered through celite washing with Et2O and the solvent removed under reduced pressure. The residue was dissolved in CH2Cl2/H2O and extracted three times with CH2Cl2. The combined organic extracts were washed with a saturated aqueous solution of NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel, 1:9 EtOAc:pet ether) to provide the title compound as a clear oil (300 mg, 1.32 mmol, 95%):

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Brear, Paul; North, Andrew; Iegre, Jessica; Hadje Georgiou, Kathy; Lubin, Alexandra; Carro, Laura; Green, William; Sore, Hannah F.; Hyvoenen, Marko; Spring, David R.; Bioorganic and Medicinal Chemistry; vol. 26; 11; (2018); p. 3016 – 3020;,
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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 1813-33-8 as follows. Recommanded Product: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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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. 1223434-15-8, name is Methyl 4-bromo-2-cyanobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-bromo-2-cyanobenzoate

A mixture of Compound II (980 mg), 2N aqueous lithium hydroxide solution (6.1 mL) and methanol (18 mL) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with 4N hydrochloric acid, and then extracted with chloroform. The chloroform layer was dried over sodium sulfate, and then concentrated under reduced pressure to give Compound III (808 mg).

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; Dainippon Sumitomo Pharma Co., Ltd.; HORIUCHI, Yoshihiro; FUJIWARA, Hiroaki; SUDA, Hitoshi; SASAKI, Izumi; IWATA, Mitsutaka; SAWAMURA, Kiyoto; EP2612848; (2013); A1;,
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Related Products of 75344-77-3, The chemical industry reduces the impact on the environment during synthesis 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, I believe this compound will play a more active role in future production and life.

Under a nitrogen atmosphere, Add 2.52 g (12 mmol) to a 250 ml three-neck round bottom reaction flask4-bromo-3,5-dimethylbenzonitrile and 2.814 g (16 mmol) of 4,4,5,5-tetramethyl-2-(3,4,5-trifluorophenyl)-1,3, 2-dioxaborolan,Then, 120 ml of toluene, 50 ml of ethanol was added, and then 40 ml of a saturated solution of potassium carbonate (2 mol/L) was added and stirred. After 15 minutes of aeration, tetrakis(triphenylphosphine)palladium 100 mg (0.087 mmol) was added and aeration was continued for 15 minutes. The reaction system was heated to 85 C and stirred at reflux overnight.After the reaction was stopped to return to room temperature, the solvent of the reaction system was removed by rotary evaporation. The reaction system was extracted with dichloromethane and washed three times with deionized water and three times with brine.The product was purified by column chromatography using a mixture of petroleum ether and dichloromethane in a ratio of 3:1.Finally, 2.8 g of a white solid 3′,4′,5′-trifluoro-2,6-dimethyl-[1,1′-biphenyl]-4-carbonitrile (intermediate product) was obtained.The yield was 89.2%.

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, 4-Bromo-3,5-dimethylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); A;,
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Reference of 179897-89-3, These common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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 compound 1 (5.0 mmol), alkylamine (15.0 mmol),and K2CO3 (15.0 mmol) in DMF (10 mL) was reacted at 70e80 C for3e5 h. After the reaction was complete, the mixture was pouredinto H2O (100 mL) and extracted with ethyl acetate (100 mL 2).The organic layer was collected, washed with brine (100 mL 3),dried over anhydrous Na2SO4, and concentrated under vacuum toyield the crude product, which was purified by flash columnchromatography (0e15% ethyl acetate in petroleum ether).

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Haiyan; Li, Xiaolei; Li, Yuanyuan; Zhu, Xinying; Zhang, Lei; Li, Jing; European Journal of Medicinal Chemistry; vol. 186; (2020);,
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