Category: nitriles-buliding-blocks

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. 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4,4-Dimethyl-3-oxopentanenitrile

General procedure: A microwave tube was charged with ketonitrile (2.0 mmol), methanol (1 mL), and hydrazine monohydrate (2.6 mmol) and subjected to microwave irradiation (100 W, 150 C) for 5 minutes. Volatiles were subsequently removed under reduced pressure. The residue was purified by either trituration with cold methanol or cyclohexane, or by using column chromatography to give the final product.

The synthetic route of 59997-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kelada, Mark; Walsh, John M. D.; Devine, Robert W.; McArdle, Patrick; Stephens, John C.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 122 – 1228;,
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Synthetic Route of 114344-60-4, A common heterocyclic compound, 114344-60-4, name is 2-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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: 9-Amino-4-X-5-bromo-2-(alkyl)-2,3-dihydropyrrolo[3,4-b]quinolin-1-one (X = H or F).A white slurry of 4-X-3-bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (1.0 equiv) in t-butanol (0.08-1.00 M) was warmed to 45 C and treated with sodium t-butoxide (1.2 equiv). The resulting green solution was heated at 45 C for 3 h. The reaction was cooled to room temperature, partitioned between methylene chloride and water and the organic layer was washed with saturated aqueous sodium bicarbonate and the combined aqueous layers were extracted with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a light tan solid in greater than 80% yield, which was used without further purification.The intermediate compounds were prepared as follows:4-X-3-Bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (X = H or F).2-Amino-3-bromo-4-X-benzonitrile (1.0 equiv) and 1-(alkyl)-4-methoxy-1H-pyrrol-2(5H)-one (2.0 equiv) were combined in acetic acid (0.5-0.8 M benzonitrile in HOAc) and heated to 80 C. Methanesulfonic acid (2.5 equiv) was dissolved in acetic acid (10 M) and added dropwise via syringe over 15 min. The reaction was stirred for 1 h at 80 C and then cooled to rt and placed on a rotary evaporator under high vacuum for 15 min at 55 C to remove the acetic acid. The resulting oil was dissolved in methylene chloride and slowly added dropwise over 20 min to a solution of saturated aqueous sodium bicarbonate at 0-5 C, maintaining the pH value above 8. The resultant precipitate from the biphasic system was separated, washed with water twice and then with hexane once, and was dried at 50 C under high-vacuum to give a tan solid as the title compound in 70-85% yield, which was used without further purification (see Table 8).

The synthetic route of 114344-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
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Electric Literature of 63069-50-1, A common heterocyclic compound, 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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: To the solution of 19 chloro-6, 7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (0.22mmol) and substituted anilines (0.22mmol) in 46 1,4-dioxane (2mL) was added 47 Pd2(dba)3 (0.05mmol), X-Phos (0.05mmol) and 48 Cs2CO3 (0.55mmol). The reaction was heated to reflux under nitrogen gas for overnight. Then the mixture was diluted with ethyl acetate, washed with brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography to give the 20 product. 4.1.8 50 tert-butyl 4-((2-((4-(methylsulfonyl)phenyl)amino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (12)

The synthetic route of 63069-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fang, Yuanying; Xiong, Lijuan; Hu, Jianguo; Zhang, Shaokun; Xie, Saisai; Tu, Liangxing; Wan, Yang; Jin, Yi; Li, Xiang; Hu, Shaojie; Yang, Zunhua; Bioorganic Chemistry; vol. 86; (2019); p. 103 – 111;,
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Reference of 606080-43-7,Some common heterocyclic compound, 606080-43-7, name is Methyl 2-cyano-5-fluorobenzoate, molecular formula is C9H6FNO2, 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.

A mixture of methyl 2-cyano-5-fluorobenzoate (11.2 g, 62.5 mmol), tert-butyl piperazine-1-carboxylate (15.1 g, 81.3 mmol) and potassium carbonate (9.50 g, 68.8 mmol) in DMSO (130 mL) was stirred at room temperature for 1 day. The mixture was diluted with water and precipitates formed were collected by filtration, washed with water and was dissolved in a mixture of ethyl acetate and methanol. The solution was washed with water and concentrated in vacuo. The residue was crystallized from ethyl acetate-hexane to give 13 (9.89 g, 46%). 1H NMR (CDCl3) delta 1.49 (s, 9H), 3.363.39 (m, 4H), 3.593.61 (m, 4H), 3.99 (s, 3H), 6.99 (dd, J = 2.7 Hz, 8.8 Hz, 1H), 7.54 (d, J = 2.7 Hz, 1H), 7.63 (d, J = 8.8 Hz, 1H). Anal. Calcd for C18H23N3O4: C, 62.59; H, 6.71; N, 12.17. Found: C, 62.52; H, 6.57; N, 12.11.

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

Reference:
Article; Yamashita, Tohru; Kamata, Makoto; Endo, Satoshi; Yamamoto, Mitsuo; Kakegawa, Keiko; Watanabe, Hiroyuki; Miwa, Katsuhiko; Yamano, Toru; Funata, Masaaki; Sakamoto, Jyun-Ichi; Tani, Akiyoshi; Mol, Clifford D.; Zou, Hua; Dougan, Douglas R.; Sang, BiChing; Snell, Gyorgy; Fukatsu, Kohji; Bioorganic and Medicinal Chemistry Letters; vol. 21; 21; (2011); p. 6314 – 6318;,
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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. 263159-64-4, name is 2-Bromo-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6BrN

To a solution of 2-bromo-3-methylbenzonitrile (12 g, 51 mmol, 1.0 eq) in tetrachloromethane (127.5mL) was added N-bromosuccinimide (10 g, 56.1 mmol, 1.1 eq) and Bz2O2 (0.075 g, 0.31 mmol, 0.006 eq) at r.t. The reaction flask was vacuumed and backfilled by nitrogen. The reaction was stirred at reflux overnight. The reaction was cooled and stirred at r.t. Insoluble matter was removed by filtration. The filtrate was cooled with ice-water, and then filtered to give 2-bromo-3- (bromomethyl)benzonitrile (7.6 g, yield 54%): Purity by IH-NMR: 90%.

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 263159-64-4.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; ZHOU, Huchen; DING, Dazhong; ZHOU, Yasheen; ZHANG, Yong-Kang; PLATTNER, Jacob J.; WO2011/22337; (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. 78881-21-7, name is 4-Amino-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2

In a round-bottomed flask 4-amino-3-methylbenzonitrile (Alfa Aesar; 10.88 g, 82 mmol), and Et3N (22.95 mL, 165 mmol) were stirred in DCM (200 mL) at 0C. TFAA (13.95 mL, 99 mmol) was added slowly via a dropping funnel and the mixture stirred at room temperature for 30 min. The reaction mixture was poured into 2M HCI (150 mL). The organic layer was then collected and then washed with a saturated solution of sodium bicarbonate (150 mL), dried (MgSC^), filtered and the solvent was removed to give a dark yellow solid (19.37 g);m/z (ES”) 227 (M-1 ); H NMR (400 MHz, CDCI3): delta 8.43 (1 H, d), 7.91 (1 H, bs), 7.59 (1 H, dd), 7.56 (1 H, s), 2.37 (3H, s).

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 78881-21-7.

Reference:
Patent; PROXIMAGEN LIMITED; DINNELL, Kevin; LIGHTFOOT, Andrew; MORTON, Gillian Elizabeth; WO2011/45353; (2011); A1;,
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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. 21524-39-0, name is 2,3-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2,3-Difluorobenzonitrile

General procedure: To a soln. of C-5 (1 eq) in DMSO (1.5 mL/mmol) was added K2CO3 (2 eq) and BB-8 (1.2 eq). The rxn mixture was heated at a given temperature for a given time (see Table 44) and was partitioned between DCM and water. The org. phase was washed with water (3x) and with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using EtOAc/MeOH.2,

The synthetic route of 21524-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (2019); A1;,
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Application of 1147558-43-7, The chemical industry reduces the impact on the environment during synthesis 1147558-43-7, name is 4-Amino-3-chloro-5-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

3.123.2. Step ii): 4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2- pyridyl]amino]-3-chloro-5-fluoro-benzonitrtte A mixture of 6-chloro-N2,N2-bis[(4-methoxyphenyl)methyl]-N4-methyl-3-nitro-pyridine-2,4- diamine (3.39 mmol), 4-amino-3-chloro-5-fluoro-benzonitrile (6.78 mmol) and CS2CO3 (13.6 mmol) in DMA (15 mL) is stirred for 16 h at 120 C. A solution of saturated NH4C1 is added to the mixture. The solid is filtered out and further washed with water. The solid is taken up in EtOAc and the organic mixture is washed (H20 and brine), dried (Na2S04) and concentrated. The residue is purified by flash column chromatography (S1O2, 100:0 to 50:50 petroleum ether/EtOAc) to afford the desired product.

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-Amino-3-chloro-5-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
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Electric Literature of 115279-57-7, 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

[00336] The synthesis of this monomer proceeds first by synthesis of the Suzuki reaction coupling partner (3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolane)quinolin-6-yl)-N-boc- methanamine starting from methyl 3-bromoquinoline-6-carboxylate. Reduction of the methyl ester with lithium aluminum hydride followed by Mitsunobu reaction with phthalimide and hydrazine cleavage provides the benzylic amine. Protection of the benzylic amine with di- tert-butyl dicarbonate followed by a Miyaura borylation reaction provides (3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolane)quinolin-6-yl)-N-boc-methanamine. (1585) [00337] An SNAr reaction of 2-(4-aminophenyl)-2-methylpropanenitrile with 6-bromo-4- chloro-3-nitroquinoline provides the substituted amino-nitro-pyridine. Reduction of the nitro group with Raney-Ni under a hydrogen atmosphere followed by cyclization with trichloromethyl chloroformate provides the aryl -substituted urea. Substitution of the free N-H of the urea with methyl iodide mediated by tetrabutyl ammonium bromide and sodium hydroxide followed by Suzuki coupling of (3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolane)quinolin-6-yl)-N-boc-methanamine and then Boc-deprotection using TFA produces the TFA salt.

The chemical industry reduces the impact on the environment during synthesis 2-(4-Aminophenyl)-2-methylpropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REVOLUTION MEDICINES, INC.; SEMKO, Christopher; PITZEN, Jennifer; WANG, Gang; TIBREWAL, Nidhi; AGGEN, James Bradley; THOTTUMKARA, Arun P.; BURNETT, G. Leslie; GLIEDT, Micah James Evans; KISS, Gert; WON, Walter; LEE, Julie Chu-li; GILL, Adrian Liam; (538 pag.)WO2018/204416; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 867366-91-4, name is 3-Bromo-5-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 867366-91-4, SDS of cas: 867366-91-4

Step 2 A solution of 3-bromo-5-methoxybenzaldehyde (4.02 g, 18.7 mmol) and hydroxylamine hydrochloride (6.50 g, 93.5 mmol) in pyridine (50 ML) and EtOH (50 ML) was heated to 65 C. for 16 h.The solvent was removed, and the remaining materials were partitioned between 1:1 EtOAc/hexanes (150 ML) and H2O (75 ML).The organic layer was washed with brine (60 ML), and the solvents were evaporated.The remaining oil was dissolved in anhydrous dioxane (50 ML), and trifluoroacetic anhydride (5.1 ML, 37.4 mmol) and pyridine (9.07 ML, 112.2 mmol) were added.The mixture was heated to 60 C. for 3 h and then cooled to RT. CHCl3 (100 ML) was added, and the organic layer was washed with H2O (2*50 ML), 5% aqueous HCl solution (30 ML), brine (30 ML), and dried with anhydrous MgSO4.The solvents were removed to provide a white solid.This solid was placed in a 150 ML flask that was flushed with nitrogen.Collidine (40 ML) and LiI (7.92 g, 59.10 mmol) were added, and the mixture was heated to 180 C. for 5 h.The reaction mixture was cooled to RT, and partitioned between H2O (400 ML) and EtOAc (100 ML).The layers were separated, and the aqueous layer was acidified with 10% aqueous HCl solution, and extracted with 2:1 EtOAc/hexanes (3*125 ML).The combined organic layers were washed with H2O (100 ML), 10% aqueous HCl solution (2*50 ML), brine (75 ML), and dried with anhydrous MgSO4.The solvents were evaporated and the resulting solid was purified by flash chromatography on silica gel (10% to 40% EtOAc/hexanes) to provide 3.40 g (92%) of 3-bromo-5-hydroxybenzonitrile (116)116).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
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