Month: September 2021

Electric Literature of 20099-89-2,Some common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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 vial containing a mixture of 2-aminopyridine (1) (1 mmol), and alpha-bromoketone (2) (1 mmol) was placed in a microwave synthesiser. The vial was subjected to microwave irradiation programmed at 65 C, 120 W and 1 bar pressure. After 15-20 min of irradiation, the mixture was cooled to room temperature. The crude product (3) was subjected to column chromatography on alumina (solvent: dichloromethane) to obtain the pure products.

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

Reference:
Article; Kong, Dulin; Wang, Xianghui; Shi, Zaifeng; Wu, Mingshu; Lin, Qiang; Wang, Xin; Journal of Chemical Research; vol. 40; 9; (2016); p. 529 – 531;,
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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. 72115-09-4, name is 5-Amino-2-bromobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Amino-2-bromobenzonitrile

Step A: tert-Butyl 2-(4-amino-2-cyanophenyl)acetate: To a solution of 5-amino-2- bromobenzonitrile (400 mg, 2.03 mmol) in THE (8 mL) were added Pd2(dba)3 (149 mg, 0.162 mmol), X-Phos (116 mg, 0.244 mmol). The reaction mixture was degassed and filled with nitrogen, followed by addition of 2-(tert-butoxy)-2-oxoethyzink chloride (10.15 mL, 5.08 mmol). The reaction mixture was heated at 60 C overnight, cooled to RT, quenched with satNH4C1, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was purified with preparative TLC (1500 uM, hex/EA=7/3) to give tert-butyl 2-(4-amino-2-cyanophenyl)acetate.LCIMS: [(M+23)] = 255.2

The synthetic route of 72115-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DEJESUS, Reynalda, Keh; FRIE, Jessica, L.; PIO, Barbara; TANG, Haifeng; WALSH, Shawn, P.; WO2014/99633; (2014); A2;,
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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. 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile

A mixture of Compound I (2.00 g, 4.59 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1 .19 g, 4.69 mmol), Pd(PPli3)4 (268 mg, 0.230 mmol), potassium carbonate (1.90 mg, 13.78 mmol) in degassed deionized water (6 mL) and degassed THF ( 18 mL) solution was stirred at 80 C under a nitrogen atmosphere for 18 h. After cooled to room temperature, the reaction mixture was filtered through a Ceiite pad rinsed by chloroform, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel using 3:2 (v/v) hexane/toluene as eluent to afford a white solid (0.962 g, 43.4%). HNMR (500 MHz, CDCb, d): 8.94 (d, J = 8 0 Hz, 1H), 8.86 (s, 1H), 8.77 (d, ./ = 8.0 Hz, 4H), 7.77 (f ./= 7.5 Hz, 1H), 7.70 (d, J= 7.5 Hz, 1H), 7 66-7 57 (m, 6H).

The synthetic route of 17823-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYULUX, INC.; CHENG, Shuo-Hsien; CHO, Yong, Joo; SUZUKI, Yoshitake; YANG, Yu, Seok; NOTSUKA, Naoto; ENDO, Ayataka; KAKIZOE, Hayato; YOSHIZAKI, Makoto; AGUILERA-IPARRAGUIRRE, Jorge; (264 pag.)WO2019/191665; (2019); A1;,
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Synthetic Route of 139152-08-2, A common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, molecular formula is C8H2Cl2N2, 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 9-phenanthrol (1) (0.97 g, 5 mmol) and4,5-dichlorophthalonitrile (2) (0.985 g, 5 mmol) in 50 mLof DMSO at 25 C was added lithium hydroxide monohydrate(0.21 g, 5 mmol) within 0.5 h. The mixture was stirred for 24 h at same temperature and then it was pouredinto 100 mL of water. Then extracted with chloroform(2 × 100 mL), washed with water (1 × 100 mL), brine(1×100 mL) and dried over Na2SO4. The solvent wasremoved under reduced pressure. The resulting residuewas purified by silica-gel column chromatography usingethyl acetate:hexane (1:9) as an eluent to obtain a lightyellow solid, yield (1.45 g, 82%). 1H NMR (600 MHz,CDCl3: delta 8.79 (d, J = 82 Hz, 1H), 8.73 (d, J = 82 Hz,1H), 7.95 (s, 1H), 7.91-7.84 (m, 2H), 7.81-7.62 (m, 4H),7.44 (s, 1H), 7.06 (s , 1H) ppm; 13C NMR (150 MHz,CDCl3: delta 157.10, 146.53, 134.58, 131.30, 130.13, 128.32,128.10, 127.47, 127.24, 126.65, 126.56, 126.27, 124.28,122.46, 121.90, 120.65, 119.66, 115.24, 114.65, 113.25,108.98, 28.67 ppm; IR (KBr tablet) max/cm-1: 3104,3040, 2900, 2233, 1628, 1584, 1510, 1303, 1198, 1128;ESI-MS: 354 [M]+.

The synthetic route of 139152-08-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Changkyeom; Kumar, Rangaraju Satish; Mergu, Naveen; Jun, Kun; Son, Young-A; Journal of Nanoscience and Nanotechnology; vol. 18; 5; (2018); p. 3192 – 3205;,
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Application of 873-74-5, A common heterocyclic compound, 873-74-5, name is 4-Aminobenzonitrile, molecular formula is C7H6N2, 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 1 Preparation of 4-Amino-3,5-dibromobenzonitrile STR15 To a stirred solution of 100 mg (0.847 mmoles) of p-aminobenzonitrile in 3.6 mL dioxane chilled in an ice-bath was added sequentially 356 muL (1.78 mmoles) of 5 N sodium hydroxide solution and 284 mg (1.78 mmoles) of bromine. The ice-water bath was removed and the reaction mixture was stirred further for 1.5 hours. After this time, 21.8 muL (0.423 mmoles) of bromine was added to drive the reaction to completion and stirring was continued for 10 minutes. The mixture was partitioned between ethyl acetate and ice-water and the organic phase was separated. It was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (7:3) as eluant provided 175 mg (74%) of the entitled product. NMR(CDCl3) delta: 5.1 (bs, 2H), 7.66 (s, 2H).

The synthetic route of 873-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5192758; (1993); A;,
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Synthetic Route of 118431-88-2, 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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a cooled solution of potassium ieri-butylate (91.6mmol, 1.1 equiv.) in THF (260ml) was added a solution of 3-cyclopropyl-3-oxo-propionitrile (83.2mmol, 1.0 equiv.) in THF (130ml) over 30 minutes, while maintaining the temperature at 0C. After stirring for an additional hour at 0C, the solution was cooled to -20C. The respective isothiocyanate (83.2mmol, 1.0 equiv.) was dissolved in THF (130ml) and added to the orange solution over 25 minutes. The reaction mixture was allowed to warm to room temperature. TLC indicated complete conversion of starting material. The clear solution was poured onto ice-cold IN HCl (1L), extracted with dichloromethane (1L), dried over Na2SO4 and evaporated to dryness. The resulting raw-solid was recrystallized from MTBE.

The chemical industry reduces the impact on the environment during synthesis 3-Cyclopropyl-3-oxopropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALGIAX PHARMACEUTICALS GMBH; HASSE, Birgit; KOOPMANS, Guido; (41 pag.)WO2015/140081; (2015); A1;,
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Electric Literature of 447-60-9, 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 447-60-9 as follows.

To a solution of 2,2,6,6-tetramethylpiperidine (0.99 g, 7.02 mmol) in THF (25 ml) was added n-BuLi (2.80 ml, 2.5 M hexane solution, 7.02 mmol) at -10 C. After stirring for 10 min, this solution was cooled to -78 C., tris(1-methylethyl)borate (1.58 g, 8.4 mmol) was added, and the mixture was stirred for 5 min. To this solution was added a solution of 2-(trifluoromethyl)benzonitrile (1.00 g, 5.85 mmol) in THF (10 ml), and the mixture was stirred at -78 C. for 2 hr. The reaction solution was allowed to warm to room temperature, the reaction was quenched with acetic acid, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the precipitated solid was filtered off, and the filtrate was concentrated to give the title compound (3.14 g) as a mixture. This was used for the next reaction without performing further purification and identification.

According to the analysis of related databases, 447-60-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kasai, Shizuo; Kamaura, Masahiro; Cho, Nobuo; US2011/251187; (2011); 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. 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H8N2O2

To a suspension of 3- (chlorosulfonyl) benzoic acid (10.8 g, 49.0 mmol) in CH2Cl2 (105 mL) and three drops [OF DMF] was added oxalyl chloride (12.5 mL) and the reaction was stirred at rt overnight. The solution was concentrated in vacuo, diluted with [CH2C12] (100 mL), and the solution was divided into two reactions. A 50 mL (24.5 mmol) aliquot of the acid chloride was added to a solution of PHA-522499 (4.49 g, 25.5 mmol) dissolved in [CH2C12] (50 mL) and pyridine (3.0 [ML)] and stirred at rt overnight. The solution was diluted with MTBE, washed with 2 N HC1 and brine, concentrated, [TRITURATED WITH MTBE] to afford 7.91 g [(85%)] of methyl [2-{[3-] (chlorosulfonyl) benzoyl] [AMINO}-5-CYANOBENZOATE] as a tan [SOLID. 1H NMR (400 MHZ,] [DMSO-D6)] [8] 11.73 (s, 1 H), 8.67 (d, [J=] 9 Hz, [1] H), 8.37 (d, [J=] 2 Hz, 1 H), 8.25 (s, 1 H), 8.12 (dd, J= 9,2 Hz, 1 H), 7.92 (d, J= 8 Hz, [1] H), 7. [88] (d, J= 8 Hz, 1 H), 7.60 (t, [J= 8 HZ, 1 H),] 3.93 (s, 3H).

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 159847-81-1.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
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Electric Literature of 2042-37-7, A common heterocyclic compound, 2042-37-7, name is 2-Bromobenzonitrile, molecular formula is C7H4BrN, 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: K3PO4 (5.62 mmol) in DMSO (4 mL), were added Cu(OAc)2 (0.28 mmol). The flask was evacuatedand backfilled with argon for three times. The resulting suspension was heated in a 80 C oil bathwith stirring for the indicated time. The reactor was cooled to r.t., the flask was opened to air and thereaction mixture was poured into water (20 mL), extracted with ethyl acetate (20 mL × 3), andorganic layer was washed with water (20 mL × 2) and once with brine (25 mL), dried overmagnesium sulfate and concentrated in vacuo. The product was purified by column chromatographyon silica gel using petroleum ether and ethyl acetate as eluent.1-(2-Methoxyphenyl)-1H-pyrrole (3a) [30]: colorless oil (0.43 g, 88%). 1H-NMR (400 MHz, CDCl3) delta (ppm):7.30-7.23 (2H, m), 7.03-6.98 (4H, m), 6.30 (2H,

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

Reference:
Article; Yuan, Chunling; Zhang, Lei; Zhao, Yingdai; Molecules; vol. 24; 22; (2019);,
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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. 17626-40-3, name is 3,4-Diaminobenzonitrile, A new synthetic method of this compound is introduced below., name: 3,4-Diaminobenzonitrile

In a round bottom flask (250ml) 3,4-dichloro-1-(hexadecan-6-yl)-1H-pyrrole-2,5-dione (10g, 25.6 mmol) wasdissolved under argon in 150ml of absolute ethanol. Sodium acetate (2.5g, 30.7mmol) and 3,4-diaminobenzonitrile (3.4g,25.6 mmol) were added. The mixture was stirred overnight at room temperature. Ethanol was removed by distillationunder vacuum at 40C and the crude product was purified by flash chromatography onto silica gel using hexane/methylene-chloride/ethylacetate 60/35/5 as the eluent. 2.5g of pure product were obtained as yellow wax with a yield of 21%. When conditions were made harsher by heating to reflux the final product (5) was obtained (yield 40%).

The synthetic route of 17626-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Solvay SA; Caille, Jean-Raphael; Dabeux, Francois; Bolsee, Jean-Christophe; Fenoll, Mathieu; EP2808327; (2014); A1;,
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