Category: 4426-11-3

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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4426-11-3

1 -cyclopentylcyclobutanecarbonitrile[291] To a solution of cyclobutanecarbonitrile (405 mg, 5 mmol) in THF (7 mL) was added dropwise LDA (2.0 M, 2.5 mL, 5 mmol) at -78 C over 10 minutes. After stirring for 30 minutes, a solution of bromocyclopentane (888 mg, 6.0 mmol) in HMPA (268 mg, 1.5 mmol) was added and the mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with the addition of IN aqueous HC1 (10 mL) and extracted with EtOAc (20 mL x 3). The combined organic phases were washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography (petroleum ether/EtOAc =20/1) to give Example 163A (0.46 g, yield 62.3%) as a colorless oil. ? NMR (400 MHz, CDC13): ? 2.53-2.44 (m, 2H), 2.25-2.07 (m, 4H), 2.03-1.95 (m, 1H), 1.86-1.69 (m, 4H), 1.62-1.54 (m, 2H).

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 4426-11-3.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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Electric Literature of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

LiHMDS (1M in toluene, 17.7 mL, 17.7 mmol, 3.1 eq) is added dropwise to a cold (-5 C.) solution of 4-bromo-2-fluoro-pyridine [Marsais, F. et al, Journal of Organic Chemistry, (1992), 57, 565-573] (1 g, 5.7 mmol) and cyclobutanecarbonitrile (1.39 g, 17.1 mmol, 3 eq) in toluene (20 mL). The reaction mixture is allowed to warm to rt, stirred for 5 h, quenched by addition of a saturated solution of NaHCO3 and filtered through a pad of celite. The filtrate is extracted with EtOAc. The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 1:0?95:5) to afford 933 mg of the title compound as a yellow oil: ESI-MS: 237.0/239.0 [M+H]+; tR=4.27 min (System 1); TLC: Rf’0.30 (Hex/EtOAc, 9:1).

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

Reference:
Patent; Novartis AG; US2009/163469; (2009); A1;,
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Electric Literature of 4426-11-3, 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 4426-11-3 as follows.

Example 44B l-(l-(3-chlorophenyl)ethyl)cyclobutanecarbonitrile n-BuLi (4.7 mL, 11.8 mmol, 2.5 M in hexane) was added to a solution ofdiisopropylamine (1.13 g, 11.2 mmol) in THF (20 mL) at -78C. After stirring for 5 min, neat cyclobutancarbonitrile (0.8 g, 9.87 mmol) was added and the mixture was stirred at -78C for 1 hour. Then a solution of Example 44A (2.6 g, 11.8 mmol) in THF (10 mL) was added and the mixture was stirred at -78C for 1 h. The mixture was quenched with water and extracted with EtOAc (40 mL). The solvent was evaporated and the residue was used directly in the next step without further purification. LC-MS: m/z 220 (M+H).

According to the analysis of related databases, 4426-11-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD; BAYBURT, Erol, K.; CLAPHAM, Bruce; COX, Phil, B.; DAANEN, Jerome, F.; GOMTSYAN, Arthur; KORT, Michael, E.; KYM, Philip, R.; VOIGHT, Eric, A.; WO2012/19315; (2012); 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 4426-11-3 as follows. Safety of Cyclobutanecarbonitrile

Example 275B 1-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclobutanecarbonitrile To a solution of Example 275A (1.90 g, 11.4 mmol) in toluene (30 mL) was added cyclobutanecarbonitrile (1.01 g, 12.5 mmol) and potassium hexamethyldisilazide (34.2 mL, 17.1 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was poured into 1N HCl solution (50 mL) and the aqueous layer was extracted with EtOAc (3*20 mL). The combined layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by prep. TLC on silicagel (eluted with EtOAc: petroleum ether=1:10) to give the title compound (1.0 g, 4.69 mmol, 41.1% yield) as a white solid. MS: MS (M+H)+; 1H NMR (400 MHz, CDCl3): delta 7.80-7.78 (m, 1H), 7.36-7.30 (m, 3H), 3.83 (s, 3H), 3.13-3.05 (m, 2H), 2.99-2.92 (m, 2H), 2.48-2.41 (m, 1H), 2.24-2.18 (m, 1H).

According to the analysis of related databases, 4426-11-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of Cyclobutanecarbonitrile

A solution of borane in THF (1M, 296 mL, 296 mmol) was added to a solution of cyclobutanecarbonitrile (20 g, 247 mmol) in THI (60 niL) under argon, and the mixture heated under reflux overnight. The mixture was cooled in an ice-water bath and MeOH (120 niL) added dropwise while keeping the temperature of the mixture below 20 C. HCI inMeOH (4M, 300 mL) was added, againkeeping the temperature below 20 C. The resulting solutionwas heated under reflux for 2.5 h. After cooling, the mixture was concentrated. The residue was diluted with MeOH (100 niL) and concentrated, and this process was repeated. Ether was added to the residue and the mixture stirred for 30 minutes before filtering to give the title compound (25.9 g, 86%) as a white solid. H NNR (300 MHz, DMSO-d6) ppm 1.70-1.86 (m, 4H) 1.97-2.04 (m, 2H) 2,46-2.61 (m, lH) 2.75-2.84 (m, 2H) 8.02 (br 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 4426-11-3.

Reference:
Patent; Takeda Pharmaceutical Company Limited; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; US2015/57298; (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. 4426-11-3, name is Cyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of Cyclobutanecarbonitrile

Example 234A 1-(6-(trifluoromethyl)pyridin-2-yl)cyclobutanecarbonitrile Cyclobutanecarbonitrile (1.474 g, 18.17 mmol) and 2-fluoro-6-(trifluoromethyl)pyridine (2.0 g, 12.11 mmol) were dissolved in toluene (30 mL). 0.5M potassium hexamethyl disilazide (36.3 mL, 18.17 mmol) in toluene was added, the solution turned dark, and the reaction was exothermic. The brown solution was stirred overnight at ambient temperature. The reaction was quenched with saturated NH4Cl solution and diluted with EtOAc. The organic layer was washed with saturated NH4Cl solution, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica (5-50% EtOAc in heptane) to give Example 234A (1.188 g, 5.25 mmol, 43.4% yield) as a yellow liquid. MS (DCI+): m/z 244 (M+NH4). 1H NMR (300 MHz, DMSO-d6) delta 8.21 (t, J=8.0 Hz, 1H), 7.95 (d, J=4.7 Hz, 1H), 7.92 (d, J=4.5 Hz, 1H), 2.86-2.69 (m, 4H), 2.38-2.19 (m, 1H), 2.15-1.96 (m, 1H).

The synthetic route of 4426-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 4426-11-3, name is Cyclobutanecarbonitrile, 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 4426-11-3, COA of Formula: C5H7N

Intermediate 371-(4-Bromo-2-iodobenzyl)cyclobutanecarbonitrile; Lithium diisopropylamide (3.34 mL, 6.68 mmol), was added dropwise to a solution of cyclobutanecarbonitrile (0.417 g, 5.14 mmol) in THF (20 mL) at -78 C. under an argon atmosphere. The reaction mixture was stirred at -78 C. for 30 min, then was a solution of 4-bromo-1-(bromomethyl)-2-iodobenzene (see Caruso, A.; Tovar, J., D. J. Org. Chem. 2011, 76, 2227-2239., 2.51 g, 6.68 mmol) in THF (8 mL) slowly added dropwise and the reaction was allowed to reach r.t. The mixture was stirred for another 3 h and then quenched with water. The reaction mixture was partitioned between water and EtOAc, the organic layer was dried over MgSO4 and concentrated to give a crude product which was purified by flash chromatography (eluent: heptane/ethylacetae 12:1) to afford the title compound (1.71 g, 89% yield): 1H NMR (500 MHz, CDCl3) delta ppm 2.08-2.34 (m, 4H), 2.47-2.58 (m, 2H), 3.18-3.23 (m, 2H), 7.29 (s, 1H), 7.49 (dd, 1H), 8.03 (d, 1H); GC MS (EI) m/z 375 M

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 4426-11-3, name is Cyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., name: Cyclobutanecarbonitrile

l-[5-(trifluoromethyl)pyridin-2-yl]cyclobutanecarbonitrile[187] 2-Fluoro-5-(trifluoromethyl)pyridine (0.603 mL, 5 mmol) and cyclobutane- carbonitrile (0.514 mL, 5.50 mmol) were dissolved in toluene (20 mL). 1M NaHMDS (5.50 mL, 5.50 mmol) in THF was added, and the reaction stirred at ambient temperature for 3 days. The reaction mixture was quenched with water and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried with MgS04, filtered, and concentrated. The residue was chromatographed on an AnaLogix SF25-60 g column and eluted with 5% EtOAc in hexanes to give Example 115A (0.36 g, 1.592 mmol, 31.8% yield). MS (DCI+): m/z 244.0 (M+NH4). XH NMR (300 MHz, DMSO-d6) ? 9.09 – 9.02 (m, 1H), 8.33 (dd, J= 8.3, 2.2 Hz, 1H), 7.85 (d, J= 8.3 Hz, 1H), 2.89 – 2.69 (m, 4H), 2.39 – 2.21 (m, 1H), 2.16 – 2.00 (m, 1H).

The synthetic route of 4426-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4426-11-3,Some common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, molecular formula is C5H7N, 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.

S nthesis of l-(5-bromo-pyridin-2-yl)-cyclobutanecarbonitrileTo a solution of lithium diisopropylamine (2.0 M in heptane/THF/ethylbenzene, 10 mL, 20.0 mmol) at -78 C is added R-4 (811 mg, 10.0 mmol). The reaction mixture is stirred at -78 C for 45 minutes, followed by the addition of R-3 (1.9 g, 8.0 mmol). The reaction mixture is allowed to warm to room temperature slowly, stirred for 16 hours, and heated at 70 C for 2 hours. The reaction mixture is allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with brine, dried with Mg2S04, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-100% EtOAc in heptane) to give the title intermediate 1-13

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
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Reference of 4426-11-3, The chemical industry reduces the impact on the environment during synthesis 4426-11-3, name is Cyclobutanecarbonitrile, I believe this compound will play a more active role in future production and life.

General procedure: l-(2-methylbenzyl)cyclobutanecarbonitrile[579] n-BuLi (0.018mol, 7.2ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at -78C. After 5 minutes neat cyclobutancarbonitrile (1.2g, 0.015mol) was added and the mixture was stirred at -78 C for 1 hour. Then a solution of 1 -(bromomethyl)-2-methylbenzene (3.3 g, 0.018 mol) in THF (3 mL) was added and the mixture was stirred at -78 C for 1 hour. The mixture was quenched with water and extracted with EtOAc. The organic phase was concentrated and the residue was directly used to the next step without further purification. MS: m/z 186 (M+H)

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, Cyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts