Month: January 2021

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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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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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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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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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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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 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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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 654-70-6, Product Details of 654-70-6

Compound 62 is prepared as in Example 4, followed by epoxidation to yield compound 65 as presented in Figure IF. An opening of the epoxide ring with 4-cyano-3-trifluoromethyl-aniline yields compound XXXVI, as presented in Figure IF.

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:
Patent; OSURF (OHIO STATE UNIVERSITY RESEARCH FOUNDATION); UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; WO2008/11072; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 623-00-7, 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. 623-00-7, name is 4-Bromobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a 25mL round bottom flask containing 5mL of ethyleneglycol, aryl halide (1 equiv), trimethoxyphenylsilane (1.5equiv), NaOH (3 equiv) and Pd NPs (0.2mol%) were takenand stirred at 100C for required time. The reaction masswas cooled to room temperature after reaction completion(as monitored by TLC), followed by the recovery of Pd NPsby centrifugation at 6000rpm for 30min. The product wasthen extracted using dichloromethane (2 ¡Á 20mL) and subjectedto water wash (1 ¡Á 20mL) and brine wash (1 ¡Á 20mL)followed by drying of the organic layer over Na2SO4.Thedried organic layer was concentrated in vacuo, and the productwas purified by column chromatography using n-hexaneand ethyl acetate as eluents to aford the corresponding productsin good to excellent yields. All the coupled productswere known molecules and were confirmed by comparingthe melting point, 1H NMR and LC-MS data with authenticsamples (see Supporting Information for details).

The chemical industry reduces the impact on the environment during synthesis 4-Bromobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kandathil, Vishal; Dateer, Ramesh B.; Sasidhar; Patil, Shivaputra A.; Patil, Siddappa A.; Catalysis Letters; vol. 148; 6; (2018); p. 1562 – 1578;,
Nitrile – Wikipedia,
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Reference of 118431-88-2,Some common heterocyclic compound, 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, molecular formula is C6H7NO, 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 solution of 50 mg (0.34 mmol) of 3-oxo-3-phenylpropanenitrile and 11.6 mg (0.36 mmol) of hydrazine and 0.024 mL of acetic acid (0.37 mmol) in 3 mL of anhydrous ethanol was heated at 60 C for 24 hr. The mixture was cooled to ambient temperature and the solvent removed in vacuo. The residue was taken up in ethyl acetate, washed with saturated sodium bicarbonate. The organic layer was washed with brine and dried over MgSO4, filtered and evaporated. The solid residue waswashedwithethyl ether and dried in vacuo to give 45 mg (82%) of 3-phenyl-1H-pyrazol-5-amine.

The synthetic route of 118431-88-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rana, Sandeep; Sonawane, Yogesh A.; Taylor, Margaret A.; Kizhake, Smitha; Zahid, Muhammad; Natarajan, Amarnath; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3736 – 3740;,
Nitrile – Wikipedia,
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