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., Safety of Cyclobutanecarbonitrile

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4426-11-3, These common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, 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.

[00140] To a mixture of cyclobutanecarbonitrile (0.70 g, 8.6 mmol) and 2-chloro-6- fluorobenzoic acid (0.5 g, 2.9 mmol) in THF (9.6 mL) at 0 C was added KHMDS (0.5M in toluene, 12.6 mL, 6.3 mmol). The resulting mixture was heated at 70 C for 3h, then cooled down, concentrated in vacuo. The residue was taken up in 20mL H20, and extracted with Et^O for three times. The aqueous layer was acidified with 2N HC1, and extracted with CHCI3/1- PrOH (3: 1). The combined organics were dried over Na2SC>4, concentrated. The crude residue was used directly. MS: 236 (M+l). XH NMR (600 MHz, DMSO-d6): delta 12.9-13.1 (brs, 1H), 7.51 (dd, 1H, J= 8.4, 1.2Hz), 7.46 (t, lH, J= 8.4 Hz), 7.30 (dd, 1H, J= 8.4, 1.2 Hz), 2.56- 2.68(m, 4H), 2.22-2.32 (m, 1H), 1.84-1.90 (m, 1H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAPOINTE, Blair, T.; FULLER, Peter, H.; GUNAYDIN, Hakan; LIU, Kun; SCOTT, Mark, E.; TROTTER, B., Wesley; ZHANG, Hongjun; (211 pag.)WO2017/75182; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route 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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route 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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 240A 1-[2-(trifluoromethyl)pyridin-4-yl]cyclobutanecarbonitrile A solution of cyclobutanecarbonitrile (1.36 g, 16.77 mmol) and 4-chloro-2-(trifluoromethyl)pyridine (2.89 g, 15.92 mmol) in anhydrous THF (55 mL) was chilled to -75 C. 1.0M lithium hexamethyl disilazide (24 mL, 24.00 mmol) in THF was added dropwise, and the reaction was permitted to warm to ambient temperature overnight. The reaction was quenched with saturated NH4Cl solution (200 mL) and extracted with EtOAc (300 mL). The organic layer was washed with saturated NH4Cl solution (200 mL), dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica (5-50% EtOAc in heptane) to give Example 240A (2.162 g, 7.65 mmol, 48% yield) as an orange oil. LC/MS (APCI+): m/z 227 (M+H). 1H NMR (300 MHz, DMSO-d6) delta 8.84 (d, J=5.1 Hz, 1H), 8.00 (d, J=1.3 Hz, 1H), 7.90-7.82 (m, 1H), 2.89-2.66 (m, 4H), 2.42-2.22 (m, 1H), 2.13-1.90 (m, 1H).

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.

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.

Example 116A 1-[4-(trifluoromethyl)pyridin-2-yl]cyclobutanecarbonitrile 2-Fluoro-4-(trifluoromethyl)pyridine (0.731 mL, 6 mmol) and cyclobutane-carbonitrile (0.841 mL, 9.00 mmol) were dissolved in toluene (10 mL). 0.5M KHMDS (18.00 mL, 9.00 mmol) in toluene 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 MgSO4, filtered, and concentrated. The residue was chromatographed on an AnaLogix SF25-60 g column and eluted with 10% EtOAc in hexanes to give Example 116A (0.88 g, 3.89 mmol, 64.8% yield). MS (DCI+): m/z 227.2 (M+H), 244.1 (M+NH4). 1H NMR (300 MHz, DMSO-d6) delta 8.93 (d, J=5.0 Hz, 1H), 7.96-7.90 (m, 1H), 7.82 (ddd, J=5.1, 1.5, 0.7 Hz, 1H), 2.90-2.68 (m, 4H), 2.35-2.21 (m, 1H), 2.13-2.00 (m, 1H).

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.

Application 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.

(a) A solution of borane-tetrahydrofuran complex [(1M] in tetrahydrofuran, [120ML)] was added over [10MIN] to a solution of cyclobutane carbonitrile (8. [1G)] [Lancaster] in dry tetrahydrofuran [(20ML)] under nitrogen at room temperature. The solution was refluxed overnight then cooled to [20.] Methanol [(150ML)] was added dropwise over 15mins keeping the temperature below [25,] then the mixture was cooled to [0 AND] dry hydrogen chloride was bubbled through for 30min. The resulting mixture was refluxed for 90min, evaporated and the residue re-evaporated twice from methanol. Ether [(150ML)] was added and the resulting solid was filtered off. It was taken up in hot isopropanol [(50ML),] filtered, and hot acetonitrile [(30ML)] added. The mixture was cooled and the solid filtered off to give the [C-CYCLOBUTYLMETHYLAMINE] hydrochloride (5.7g) NMR (400 MHz, DMSO-d6) F6382 1.8 (4H, m), 2.0 (2H, m), 2.54 [(1H,] m), 2.80 (2H, d), 8.0 (3H, [BR S).]

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.

Related Products of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: tert-butyl 3 -( 1 -cyanocyclobutyl)-3 -hydroxypyrrolidine- 1 -carboxylate[619] To a solution of cyclobutanecarbonitrile (1.75 g, 21.5 mmol) in THF (15mL) was added 2.0M lithium diisopropylamide (11 mL, 22.5 mmol) dropwise and the solution was stirred at -78 C for 45 minutes. Then a solution of tert-butyl 3-oxopyrrolidine-l- carboxylate (4.0 g, 21.5 mmol) in THF (2 mL) was added to the solution and the mixture was stirred at -78 C for 2 hours. The reaction mixture was quenched with saturated NH4C1 solution and extracted with EtOAc (25 mL x 3). The organic phase was washed with brine (20 mL), dried over Na2S04, filtered, and concentrated. The residue was purified by column chromatography eluted with petroleum ether: EtOAc = 2: 1 to obtain the title compound (0.9 g, 38.2 % yield) as a white solid. XH NMR: (400 MHz, CDC13): ? 3.64-3.40 (m, 4H), 2.44 (t, J= 7.8 Hz, 2H), 2.33-2.23 (m, 2H), 2.13-1.88 (m, 4H), 1.47(s, 9H)

The synthetic route of Cyclobutanecarbonitrile 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, These common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, 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.

Example 253A 1-(2-methylbenzyl)cyclobutanecarbonitrile n-BuLi (0.018 mol, 7.2 ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at -78 C. After 5 minutes neat cyclobutancarbonitrile (1.2 g, 0.015 mol) 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)

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

Related Products 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.

A mixture of cyclobutanecarbonitrile (0.70 g, 8.6 mmol) and 2-chloro-6-fluorobenzoic acid (0.5 g, 2.9 mmol) in THF (9.6 mL) at 0 C.Was added KHMDS (0.5 M in toluene, 12.6 mL, 6.3 mmol). The resulting mixture was heated at 70 C. for 3 h, then cooled and concentrated in vacuo. The residue was taken up in 20 mL H 2 O and extracted three times with Et 2 O. The aqueous layer was acidified with 2 N HCl and extracted with CHCl 3 / i-PrOH (3: 1). The combined organic portion was dried over Na 2 SO 4 and concentrated. This crude residue was used directly.

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; Mrck Sharp and Dohme Corp; Blair T, Lapointe; Peter H, Fuller; Hakan, Gunaydin; Kun, Liu; Daneille F, Molinari; Qinglin, Pu; Mark E, Scott; B Wesely, Trotter; Hongjun, Zhang; (117 pag.)JP2018/531957; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts