Month: March 2021

Synthetic Route of 53312-81-5,Some common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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: Under nitrogen atmosphere, dry CH2Cl2 (30 mL), amine (0.02 mol), and Et3N (0.05 mol) wereadded to a three-necked round bottom ask and stirred for 0.5 h, then chloroacetyl chloride droppedslowly and reacted for 3 h at room temperature. Then, the solution was washed with 2 mol L1hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively,then dried over anhydrous Na2SO4 and filtered. After evaporating CH2Cl2 in vacuum, the obtainedcrude product was rened by recrystallization using ethyl acetate/petroleum ether.

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

Reference:
Article; Cai, Nan; Liu, Caixiu; Feng, Zhihui; Li, Xinghai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Ahmed, Wasim; Cui, Zining; Molecules; vol. 23; 4; (2018);,
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Related Products of 1080-74-6, 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 1080-74-6 as follows.

To a three-necked round bottom flask were added 5,5′-(9,9′-spirobi[fluorene]-2,7-diyl)bis(4-(2-ethylhexyl)thiophene-2-carbaldehyde) (220 mg, 0.29 mmol), 1,1-dicyanomethylene-3-indanone (432 mg, 2.2 mmol), chloroform (50 mL), and 0.9 mLpyridine. The mixture was deoxygenated with nitrogen for 30 minand then refluxed for 12 h. After cooling down to room temperature,the mixture was poured into methanol (200 mL) and filtered.The residue was purified by column chromatography on silica gelusing petroleum ether/dichloromethane (1:1) as eluent yield anorange solid (213 mg, 66%). 1H NMR (400 MHz, CDCl3): delta 8.78 (s,2H), 8.68 (d, J 6.9 Hz, 2H), 7.99 (d, J 8.1 Hz, 2H), 7.90 (m, 4H), 7.78 (m, 4H), 7.62 (d, J 8.4 Hz, 4H), 7.41 (t, J 7.5 Hz, 2H), 7.17 (t,J 7.5 Hz, 2H), 6.90 (s, 2H), 6.82 (d, J 7.5 Hz, 2H), 2.38 (d,J 7.2 Hz, 4H), 1.39 (m, 2H), 1.11 (m, 4H), 1.06 (m, 12H), 0.81 (t,J 7.2 Hz, 6H), 0.61 (t, J 7.2 Hz, 6H). 13C NMR (100 MHz, CDCl3): delta 188.78,161.17,157.01, 150.60,148.23, 148.06,142.35,141.37,140.50,138.73, 137.48, 135.75, 135.55, 135.15, 134.12, 130.13, 128.78, 128.70,125.92, 125.42, 124.50, 124.41, 123.29, 121.33, 120,89, 115.07, 114.98,70.38, 66.55, 40.61, 32.88, 32.58, 28.86, 25.82, 23.49, 14.72, 10.89.10.92. MS (MALDI): m/z calcd for C75H60N4O2S2: 1113.4; found:1113.0. Anal. Calcd for C75H60N4O2S2: C, 80.90; H, 5.43; N, 5.03.Found: C, 80.90; H, 5.47; N, 5.12.

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Jiayu; Dai, Shuixing; Yao, Yuehan; Cheng, Pei; Lin, Yuze; Zhan, Xiaowei; Dyes and Pigments; vol. 123; (2015); p. 16 – 25;,
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Related Products of 658-99-1, 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. 658-99-1 name is 2-(3,4-Difluorophenyl)acetonitrile, 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.

EXAMPLE 17; N-{[2-[(3,4-Difluorophenyl)methyl]-4-hydroxy-6-oxo-1-(phenylmethyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine; 17a) Ethyl 2-(3,4-difluorophenyl)ethanimidoate hydrochloride; 3,4-Difluoroacetonitrile (2.44 g, 15.93 mmol) and ethanol (2 mL) was sealed in a flask using a rubber septum and flushed with nitrogen. 4 Molar hydrogen chloride in dioxane (5 mL) was added and the mixture was stirred at rt overnight. The solid was diluted with diethyl ether, collected, washed with diethyl ether and dried in vacuo to give the title compound (2.87 g, 76.5%) 1H NMR (400 MHz, DMSO-d6) delta ppm 11.75 (br. s., 2 H), 7.37-7.67 (m, 2 H), 7.20-7.31 (m, 1 H), 4.41 (q, J=7.07 Hz, 2 H), 4.05 (s, 2 H), 1.29 (t, J=6.95 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3,4-Difluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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Synthetic Route of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 3 -neck flask with an internal thermometer and an addition funnel was added (i?)-(+)-2-methyl-CBS-oxazaborolidine solution in toluene (3.0 mL) and borane-dimethylsulfide (300 The reaction was stirred at room temperature for 10 min then diluted with DCM (25 mL). Borane-dimethylsulfide (6.0 mL) was added and, after stirring for 5 min, the reaction was cooled to -20C. l-Oxo-2,3-dihydro-7H- indene-4-carbonitrile INT-1 (4.7 g, 30 mmol) in DCM (25 mL) was added dropwise by addition funnel over 20 min while maintaining the reaction at -20 ¡À 5C. The reaction was stirred for 1 h then quenched by the dropwise addition of MeOH (20 mL). After hydrogen evolution ceased, MeOH (30 mL) was added and removed by heating at atmospheric pressure. MeOH (50 mL) was added in two and removed by heating twice. All the solvent was evaporated to give a solid which was recrystallized from EA (9 mL) and hexane (22 mL). The compound was filtered and washed with 5: 1 hexane/EA (30 mL) to provide 3.73 g (78%) of (5)-l-hydroxy-2,3-dihydro-iH-indene-4-carbonitrile INT-2 as a white powder. LCMS-ESI (m/z) calculated for Ci0H9NO: 159.1; found 160.1 [M+H]+, tR = 2.39 min. 1H NMR (400 MHz, CDC13) delta 7.62 (d, J = 7.6 Hz, 1H), 7.53 (d, J = 7.6 Hz, 1H), 7.32 (t, J = 7.6 Hz, 1H), 5.28 (d, J = 4.1 Hz, 1H), 3.23 (ddd, J = 17.0, 8.7, 4.4 Hz, 1H), 3.04 – 2.90 (m, 1H), 2.64 – 2.51 (m, 1H), 2.00 (dddd, J= 13.4, 8.7, 7.1, 5.7 Hz, 1H), 1.91 (d, J = 5.4 Hz, 1H). Chiral HPLC: (5)-l-hydroxy-2,3- dihydro-iH-indene-4-carbonitrile was eluted in 20% IPA in hexane: >99.9% ee, = 7.42 min. The (i?)-enantiomer was obtained in an analogous fashion using (S) -(-)-2- methyl-CBS-oxazaborolidine. for (i?)-enantiomer = 6.79 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common.

Reference:
Patent; RECEPTOS, INC.; MARTINBOROUGH, Esther; BOEHM, Marcus, F.; YEAGER, Adam, Richard; TAMIYA, Junko; HUANG, Liming; BRAHMACHARY, Enugurthi; MOORJANI, Manisha; TIMONY, Gregg, Alan; BROOKS, Jennifer, L.; PEACH, Robert; SCOTT, Fiona, Lorraine; HANSON, Michael, Allen; WO2015/66515; (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. 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3BrClN

To a stirred solution of 2-bromo-5-chloro-benzonitrile (10 g, 46 mmol) in THF (200 mL) at 0C, was added MeMgBr (77 mL, 230 mmol) dropwise. The reaction mixture was allowed to warm up to room temperature and stuffed for 2 hours. Ti(Oi-Pr)4 (13 g, 46 mmol) was added and the solution was stuffed for another 16 hours before it was quenchedwith aq. HC1 solution and washed with EtOAc. The aqueous phase was adjusted to pH10 with aq. NaOH solution, and exacted with EtOAc (3 x). The combined organic layers were concentrated to give a crude title product (3.8 g, yield 33%) as oil, which was used directly in the next step without further purification. MS: 249.30 (M+H]

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191338; (2014); A1;,
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These common heterocyclic compound, 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, 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. Recommanded Product: 950596-58-4

General procedure: A mixture of 3 (2.00mmol), toluene (5mL), and DMF-DMA (4.00mmol) were heated up to 35-40C and acetic acid (0.10mL) was added. After 15min, the resultant mixture was cooled to approximately 25C. The solvent was completely evaporated. The residue was added to water and basified pH to 13 by the addition of 20% sodium hydroxide. The obtained mixture was extracted with methylene chloride (2¡Á15mL) and the combined organic extracts were washed with water (2¡Á20mL) and brine (1¡Á70mL), then dried over anhydrous MgSO4. The organic solvent was evaporated to give 4 as oil (Yield 61-94%).

The synthetic route of 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Li; Zhang, Yaling; Liu, Juan; Wang, Weijia; Li, Xiabing; Zhao, Lijun; Wang, Wei; Li, Baolin; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 689 – 697;,
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Electric Literature of 134227-45-5, The chemical industry reduces the impact on the environment during synthesis 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, I believe this compound will play a more active role in future production and life.

C) 3,5-difluoro-4-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)benzonitrile [0934] To a solution of 4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine (250 mg), 1,4,7,10,13-pentaoxacyclopentadecane (266 mg) and 3,4,5-trifluorobenzonitrile (152 mg) in DMF (5 ml) was added sodium hydride (60%, 48.03 mg) at 0C, and the mixture was stirred at 0C for 1 hr. To the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (250 mg). MS (ESI+): [M+H]+ 448.4. MS (ESI+), found: 448.4.

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (2015); 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 54454-12-5 as follows. COA of Formula: C8H6ClN

EXAMPLE 37 Cis-2-(3-chloro-o-toluoyl)-3-hydroxycrotononitrile A 4.5 g. portion of potassium tertiary butoxide is added to 700 ml. of ether and then cooled in an ice-salt bath. To this is added, over 15 minutes, a mixture of 60.0 g. of 3-chloro-2-methylbenzonitrile and 22.0 ml. of acetonitrile in 300 ml. of ether. The mixture is stirred in the ice bath for 1/2 hour, allowed to warm to room temperature and then stirred for one hour. This mixture is poured into one liter of water and the layers are separated. The aqueous phase is extracted with ether and the ether layers are combined, washed four times with water and dried over magnesium sulfate. The crystals which form on evaporation are collected and recrystallized from 200 ml. of hot benzene giving 16.0 g. of beta-amino-3-chloro-2-methylcinnamonitrile. An 11.0 g. portion of the above product is added to 150 ml. of methanol and heated to solution on a steam bath.

According to the analysis of related databases, 54454-12-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US4173650; (1979); A;,
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Reference 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 boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).

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:
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 118431-88-2, 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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Preparation of 3-Cyclopropyl-l-(3-methyl-pyridin-2-yl)-lH-pyrazol-5-amine; To solution of S-cyclopropyl-S-oxo-propionitrile (6.4 g, 46.917 mmol) and N- benzhydrylidene-N’-(3~methyl-pyridin-2-yl)-hydrazine (7.49 g, 26.065 mmol) in ethanol(133 mL) was added p-toluene sulfonic acid (4.958 g, 26.065 mmol) and cone HCl (10 mL).The mixture was heated to reflux under nitrogen for 15 h and then concentrated. The residue was taken up in ethyl acetate (200 mL) and water (100 mL) and solid NaHCO3 added cautiously till there was no more bubbling (due to the formation of CO2 gas). The organic layer was isolated and washed with brine, then dried over Na2SO4 and concentrated. The product was isolated as a pink viscous oil (4.06 g, 40%) by column chromatography (20 %EtOAc in hexanes, then 100 % EtOAc). ES-MS m/z 215.1 (MH+); HPLC RT (min) 1.16{method (A)}.

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

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/27842; (2007); A1;,
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