Category: nitriles-buliding-blocks

Application of 96784-54-2, These common heterocyclic compound, 96784-54-2, name is 3-Methyl-4-nitrobenzonitrile, 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 stirring 100 mL solution of THF at room temperature, added 9.89 g (61 mmol, 1 eq) of the benzonitrile. Then added 1 g palladium over 10% carbon. Then added 25 mL of methanol. The system was then put under 50 psi of pressure in a hydrogenator. After no more hydrogen consumption was observed, the reaction was stopped and filtered over celite. Performed column chromatography using 1:1 hexane:dichloromethane as the mobile phase. Obtained 7.5 g of a beige powder. Yield was 93%. 1H-NMR (DMSO): delta 2.27 (3H, s), 6.06 (2H, s), 6.41 (1H, d), 6.46 (1H, s), 7.30 (1H, d).

Statistics shows that 3-Methyl-4-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 96784-54-2.

Reference:
Patent; NITTO DENKO CORPORATION; Gu, Tao; Rachwal, Bogumila; Siddiqui, Ozair; Rachwal, Stanislaw; Kitahara, Isamu; Simavoryan, Sergey; Wang, Peng; Yamamoto, Michiharu; (44 pag.)US2017/44373; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 144649-99-0, name is 5-Bromo-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 144649-99-0, category: nitriles-buliding-blocks

Preparation of Intermediate 1-2; 5-(2-Chloropyrimidin-4-yl)-2-methoxybenzonitrileReagents: (a) Pd(dppf)Cl2, KOAc, /?-dioxane: (b) 2,4-dichloropyrimidine, K2C03,Pd(PPh3)4, CH3CN, H20, reflux, 5 h;[0209] Step 1. 2-Methoxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile: To a solution of 2-methoxy-5-bromobenzonitrile (5.0 g, 23.6 mmol) in /?-dioxane (125 mL), bis(pinacolato)diborane (9.0 g, 35.4 mmol), KOAc (7.0 g, 71.3 mmol), and Pd(dppf)Cl2 (0.863 g, 1.17 mmol) were added. The resulting mixture was stirred for 18 h at 80 C. The cooled reaction crude was diluted with 120 mL EtOAc, washed with H20 and brine, dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by column chromatography on Si02 (Hexanes/EtOAc) to afford the title compound (5.6 g, 92%). GC/MS (EI, M+) 245

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MYREXIS, INC.; HOLCOMB, Ryan C.; SEBAHAR, Paul R.; SUZUKI, Kazuyuki; McLEOD, Donald A.; DASTRUP, David M.; HOARAU, Christophe; HALTER, Robert J.; BURSAVICH, Matthew Gregory; SHENDEROVICH, Mark D.; RICHARDS, Burt; BARTEL, Paul L.; WO2012/142329; (2012); A1;,
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Application of 3672-47-7, A common heterocyclic compound, 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, molecular formula is C10H9NO2, 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: The enzymatic reaction was performed biotransformations at 25mL-scale, using an enzyme-coupled system (glucose and glucose dehydrogenase from Bacillus megaterium) for cofactor recycling. Biotransformations were carried out by addition of 10mM substrate dissolved in 250muL of DMSO, 0.1mM NADP+, KRED1-Pglu (20mU/mL), GDH (1U/mL), glucose 40mM in Tris/HCl buffer pH 8.0 (0.05M, 25mL) at 30C. Biotransformations of 1k-n were also performed also in acetate buffer (NaAB 0.1M, pH 5.0). The reaction mixture was kept under stirring at 30C until completion and then extracted with 20mL of EtOAc; the aqueous phase was extracted twice more with 15mL of EtOAc. The organic phases were collected and dried over Na2SO4 and the solvent was evaporated. The crude residue was purified by flash chromatography.

The synthetic route of 3672-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Contente, Martina L.; Serra, Immacolata; Molinari, Francesco; Gandolfi, Raffaella; Pinto, Andrea; Romano, Diego; Tetrahedron; vol. 72; 27-28; (2016); p. 3974 – 3979;,
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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. 6136-93-2, name is 2,2-Diethoxyacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 6136-93-2

In a round bottom flask, ammonium sulfide (44 wt% in H2O, 17.4 mL, 112 mmol) was added to a solution of diethoxyacetonitrile (6) (11.1 mL, 80.0 mmol) in MeOH (770 mL). The mixture was stirred at room temperature for 22 h. The solvent was evaporated under reduced pressure to afford thioamide 7 (13.0 g, quantitative yield) as a pale yellow solid. TLC: Rf 0.63 (1:1 hexane/EtOAc). Mp: 87.5-89.5 C (lit.81-82 C). IR (KBr, film): 3370,3182, 2975, 1124, 1064 cm1. 1H NMR (400 MHz, CDCl3): d 7.86(br s, 1H), 7.52 (br s, 1H), 5.05 (s, 1H), 3.74 (dq, 2H, J = 9.6,7.2 Hz), 3.64 (dq, 2H, J = 9.6, 7.2 Hz), 1.26 (t, 6H, J = 7.2 Hz).13C NMR (100 MHz, CDCl3): d 202.2, 103.2, 63.1, 15.2. HRMS (ESI)m/z calculated for C6H13NO2S 163.0667, found 163.0664.

According to the analysis of related databases, 6136-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Park, Yunjeong; Bae, Song Yi; Hah, Jung-Mi; Lee, Sang Kook; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6827 – 6843;,
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These common heterocyclic compound, 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, 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. category: nitriles-buliding-blocks

A mixture of 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1 .5 g, 5.91 mmol), 3,5-bis(trifluoromethyl)phenylboronic acid (1.90 g, 7.38 mmol), Pd(PPh3)4 (0.341 g, 0.3 mmol) in toluene (70 ml) was degassed for about 1.5 hours with bubbling argon. Vacuum-oven-dried cesium carbonate (3.61 g, 1 1 .07 mmol) was added and the mixture was degassed for an additional 30 minutes and then heated to about 110 C for about about 64 hours. The resulting mixture was worked up with dichloromethane/brine, and the organic phase was collected and dried over MgS04. The crude mixture was purified twice by column chromatography on a silica gelcolumn using eluents of 0% to 3.5% ethyl acetate in hexanes, and then 5% to 30% dichloromethane in hexanes. The clean product fractions were dried by rotaryevaporation to yield Compound 21 (1.15 g, 51 % yield) as a clear crystalline solid.

The synthetic route of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
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Application of 654-70-6, The chemical industry reduces the impact on the environment during synthesis 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, I believe this compound will play a more active role in future production and life.

General procedure: In a typical experiment, a solution of sodium hydrogen carbonate (62.72 mmol) in 20 mL of water was stirred for 10 min and to it was added dichloromethane (20 mL) followed by substituted aniline (15.68 mmol). The reaction mixture was cooled to 0 C, thiophosgene (23.52 mmol) was introduced dropwise over a period of 30 min and continuously stirred at room temperature for 1 h. The reaction mixture was washed with brine solution; the organic layer was dried over anhydrous sodium sulphate and concentrated to get a crude gummy compound which was recrystalized in hexane under cold condition. The precipitate was filtered and dried to get the desired compound. The products were characterized by analytical and spectral methods.

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-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Khatik, Gopal L.; Kaur, Jasmine; Kumar, Varun; Tikoo, Kulbhushan; Venugopalan; Nair, Vipin A.; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3291 – 3301;,
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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 591769-05-0 as follows. Computed Properties of C8H11N

Racemic 3-cyclopentyl-3-{4-[7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl}propionitrile (9, racemic SEM-protected compound).; Method A.; 3-Cyclopentylacrylonitrile (8, 273.5 g, 2.257 mol, 1.20 equiv) and DBU (28 mL, 0.187 mol, 0.10 equiv) was added to a suspension of 4-(1H-pyrazol-4-yl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (5, 591.8 g, 1.876 mol) in acetonitrile (4.7 L) at room temperature. The resulting reaction mixture was heated to 50-60¡ã C. for 17 hours (a clear solution developed midway through heating) then to 70-80¡ã C. for 8 hours. When LCMS analysis showed the reaction was deemed complete, the reaction mixture was cooled to room temperature. The cooled solution was then concentrated under reduced pressure to give the crude product (9) as a thick amber oil. The crude product was dissolved in dichloromethane (DCM) and absorbed onto silica gel then dry-loaded onto a silica column (3 Kg) packed in 33percent EtOAc/heptanes. The column was eluted with 33percent EtOAc/heptanes (21 L), 50percent EtOAc/heptanes (28 L), 60percent EtOAc/heptanes (12 L) and 75percent EtOAc/heptanes (8 L). The fractions containing the desired product (9) were combined and concentrated under reduced pressure to generate a yellow oil, which was transferred to a 3 L flask with EtOAc. The solvent was removed under reduced pressure and the residual EtOAc by co-evaporating with heptanes. The residue was further dried under high vacuum for overnight to afford racemic 3-cyclopentyl-3-{4-[7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl}propionitrile (9, racemic SEM-protected compound, 800 g, 819.1 g theoretical, 97.7percent yield) as an extremely viscous yellow oil. For 9: 1H NMR (DMSO-d6, 400 MHz) delta ppm 8.83 (s, 1H), 8.75 (s, 1H), 8.39 (s, 1H), 7.77 (d, 1H, J=3.7 Hz), 7.09 (d, 1H, J=3.7 Hz), 5.63 (s, 2H), 4.53 (td, 1H, J=19.4, 4.0 Hz), 3.51 (t, 2H, J=8.1 Hz), 3.23 (dq, 2H, J=9.3, 4.3 Hz), 2.41 (m, 1H), 1.79 (m, 1H), 1.66-1.13 (m, 7H), 0.81 (t, 2H, J=8.2 Hz), 0.124 (s, 9H); C23H32N6OSi (MW, 436.63), LCMS (EI) m/e 437 (M++H) and 459 (M++Na).

According to the analysis of related databases, 591769-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
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Synthetic Route of 874472-98-7, 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 874472-98-7 as follows.

To prepare compound 109, first 2-Methoxy-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile was prepared by combining 3-bromo-2-cyanobenzonitrile (1.0 g), P(cyclohexyl)2biphenyl (200 mg), Pd2dbas (132 mg) and flushing with nitrogen. Then dioxane (32 mL), triethylamine (2.7 mL) and pinacolborane (1.5 mL) was added and the mixture heated at reflux. After 16 h, the reaction was quenched with saturated ammonium chloride, and extracted with EtOAc. The organic layers were washed with brine, dried over magnesium sulfate, an filtered. Flash chromatography (80% dichloromethane/hexanes) affords 2-methoxy-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile (416 nig)

According to the analysis of related databases, 874472-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIGAND PHARMACEUTICALS, INC.; WO2006/10142; (2006); A2;,
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These common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, 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. SDS of cas: 555-21-5

To a solution of (4-nitro-phenyl)-acetonitrile (5.00 g; 30.9 mmol) in dry DMF (30 mL) cooled at 0 C, under N2 atmosphere, was added NaH (60% dispersion in mineral oil; 1.23 g; 30.9 mmol) portionwise and the mixture was stirred for 15 min at 0C. Then iodomethane (1.92 mL; 30.9 mmol) was added and the mixture was stirred at room temperature for 1.5 hour. The reaction was re-cooled at 0C and NaH (60% dispersion in mineral oil; 1.23 g; 30.9 mmol) was added again portionwise. After stirring at 00C for 15 min, iodomethane (1.92 mL; 30.9 mmol) was added and the reaction was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the residue was taken up with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The crude was purified by chromatography [SiO2, Petroleum ether/EtOAc (95/5 to 8/2)] to give the title compound as a yellow solid (3.50 g, 60 % yield). LCMS (RT): 1.42 min (Method A); MS (ES+) gave m/z: 191.1 (MH+).

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

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); 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. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-4-fluoro-3-methylbenzonitrile

Example 4 2-Chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methylbenzonitrile, hydrochloride (165RL90) 2-Chloro-4-fluoro-3-methylbenzonitrile (165RL87a, 55 mg, 0.32 mmol) and nortropine (165 mg, 1.29 mmol) was dissolved in pyridine (2 mL) and the mixture irradiated at 220 C. for 2 hours in a microwave oven. Dichloromethane (50 mL) was added and the mixture washed with hydrochloric acid (0.4 M, 2¡Á30 mL) followed by sat. sodium hydrogen carbonate (20 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The product was further purified by column chromatography using dichloromethane to give the title compound (16.2 mg, 18%). Rf=0.45 (CH2Cl2). LC/MS m/z 277 [M+H]+. 1H-NMR (CDCl3, 300 MHz) delta 7.37 (d, 1H, J=8.6, Ar-H), 6.78 (d, 1H, J=8.6, Ar-H), 4.20 (m, 1H, Tr-H), 3.80 (m, 2H, Tr-H), 2.37 (s, 3H, Ar-CH3), 2.32-2.22 (m, 4H, Tr-H), 1.98-1,81 (m, 4H, Tr-H).

The synthetic route of 796600-15-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schlienger, Nathalie; Thygesen, Mikkel Boas; Pawlas, Jan; Badalassi, Fabrizio; Lewinsky, Rasmus; Lund, Birgitte Winther; Olsson, Roger; US2006/160845; (2006); A1;,
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