Category: 3814-30-0

These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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. Computed Properties of C6H11Br

Example 8A 2-(Trimethylsilyl)ethyl (1RS,2RS,5SR)-2-[4-(cyclopentylmethoxy)benzoyl]-5-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]cyclopentanecarboxylate (racemate) To a solution of 80 mg (0.16 mmol) of the compound from Example 4A in 1.8 ml of acetonitrile were added 45 mg (0.32 mmol) of potassium carbonate and 32 mg (0.19 mmol) of (bromomethyl)cyclopentane, and the mixture was stirred under reflux overnight. Thereafter, a further 32 mg (0.19 mmol) of (bromomethyl)cyclopentane were added, and the mixture was stirred under reflux once again for 4 h. After cooling to RT, the mixture was diluted with water and extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by means of preparative HPLC (Method 7). 33 mg (36% of theory, 100% purity) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.61 min, m/z=576 [M+H]+.

The synthetic route of (Bromomethyl)cyclopentane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (91 pag.)US2017/22171; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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 solution of 3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one (400 mg, 1.82 mmol) in anhydrous DMF (5 mL) was added K2CO3 (503 mg, 3.64 mmol) and (bromomethyl)cyclopentane (445 mg, 2.73 mmol). The reaction mixture was stirred at 60C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC-MS to afford 7-(cyclopentylmethyl)-3-(tetrahydro-2/-/-pyran-4-yl)imidazo[1 ,5- a]pyrazin-8(7H)-one 290 mg (53%). NMR (DMSO-de, 400 Mhz): delta 7.62 (s, 1 H), 7.49 (d, J = 6.0 Hz, 1 H), 6.90 (d, J = 6.0 Hz, 1 H), 3.91 -3.88 (m, 2H), 3.69 (d, J = 7.6Hz, 2H), 3.48-3.43 (m, 2H), 3.42-3.31 (m, 1 H), 2.27- 2.24 (m, 1 H), 1.78-1.73 (m, 4H), 1.58-1.44 (m, 6H) , 1.21 -1.20 (m, 2H). LC-MS: (m/z) 302.2 (MH+) tR (minutes, method 3) = 2.29 minutes .

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

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below., Recommanded Product: (Bromomethyl)cyclopentane

To a solution of 3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7H)-one (300 mg, 1.71 (0680) mmol) in anhydrous DMF (5 mL) was added K2C03 (355 mg, 2.57 (0681) mmol) and (bromomethyl)cyclopentane (335 mg, 2.05 mmol). The reaction was stirred at 65C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC- MS to yield 7-(cyclopentylmethyl)-3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7H)-one 210 mg (47%). (0682) 1H NMR (DMSO-de, 400 MHz): delta 7.53 (s, 1 H), 7.51 (d, J = 6.0 Hz, 1 H), 6.90 (d, J = 6.0 Hz, 1 H), 3.69 (d, J = 7.6 Hz, 2H), 2.29-2.24 (m, 2H), 1.58-1.45 (m, 6H), 1.22-1.19 (m, 2H), 1.00- 0.89 (m, 4H). (0683) LC-MS: {m/z) 258.2 (MH+) tR (minutes, method 3) = 2.24 minutes

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; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2018/78042; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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.

REFERENCE EXAMPLE 78 A stirred solution of 3-hydroxy-4-methoxy-benzaldehyde (5.74 g) in dry dimethylformamide (50 mL) is treated with cyclopentylmethyl bromide (7.34 g) and potassium carbonate (15 g), and the solution is heated at 60 C. for 24 hours. After cooling and filtration, the solution is evaporated to low bulk and dissolved in ethyl acetate (100 mL). The organic solution is washed with aqueous sodium hydroxide solution (4*50 mL; 2N) and water (2*50 mL), dried over magnesium sulfate, and evaporated to give 3-cyclopentyl-methoxy-4-methoxybenzaldehyde (6.5 g) in the form of a light brown oil. By proceeding in a similar manner, but using the appropriate quantity of isopropyl bromide, there is prepared 3-isopropoxy-4-methoxybenzaldehyde, in the form of a light golden oil. ?NMR (CDCl3): 9.85(s,1H), 7.46(dd,1H), 7.43(d,1H), 6.98(d,1H), 4.65(m1H), 3.94(s,3H),[1.41(d,6H)].

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

Reference:
Patent; Rhone-Poulenc Rorer Limited; US5935978; (1999); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (Bromomethyl)cyclopentane

General procedure: The alkyl bromide (1.0 equiv) was added to a solution of mercaptoaceticacid (1.0 equiv) in methanol (10.0 mL) and the resultingsolution stirred. Then a solution of NaOH (2.0 equiv) in methanol(5.0 mL)was added slowly, and the final mixturewas stirred at roomtemperature or heated to reflux until absence of the alkyl bromide(checked by TLC). The reaction mixture was concentrated in vacuo,diluted with H2O, and neutralized with 1 N HCl. Then the obtainedreaction mixture was extracted with EtOAc. The combined organicfractions were washed with brine, dried with Na2SO4, and concentratedin vacuo. Purification of the crude residue by column chromatography(petroleum ether/EtOAc) afforded the title compound.

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 3814-30-0.

Reference:
Article; Chen, Ying; Wu, Bolin; Hao, Yameng; Liu, Yunqi; Zhang, Zhili; Tian, Chao; Ning, Xianling; Guo, Ying; Liu, Junyi; Wang, Xiaowei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 420 – 433;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 3814-30-0, These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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 2-1 -1 Preparation of 4-({2-[1 -(cyclopentylmethyl)-1 H-indazol-3-yl]-5-methoxypyrimidin-4- yl}amino)pyridine-3-carboxamide 100 mg of 4-{[2-(1 H-lndazol-3-yl)-5-methoxypyrimidin-4-yl]amino}pyridine-3- carboxamide 1 -8-1 (277 muiotaetaomicronIota, 1 .0 eq.), 34 muIota_ (bromomethyl)cyclopentane (300 muetaiotaomicronIota, 1 .1 eq.) and 50 muIota_ 1 ,8-Diazabicyclo(5.4.0)undec-7-en (330 muiotaetaomicronIota, 1 .2 eq.) were dissolved in 2.1 mL DMF and stirred at rt for 3 days. The reaction mixture was diluted with water and ethyl acetate and extracted three times. The organic layers were washed once with water and brine, filtered through a silicon coated filter and concentrated in vacuo. The crude product was purified by HPLC-chromatography under basic conditions to provide the 96% pure target compounds: 12 mg, 30 muiotaetaomicronIota, 10% 1 H-NMR (400MHz, DMSO-d6) : delta [ppm]= ]= 1 .37 – 1 .49 (m, 2H), 1 .49 – 1 .62 (m, 2H), 1 .63 – 1 .76 (m, 4H), 2.54 – 2.63 (m, 1 H), 4.07 (s, 3H), 4.47 (d, 2H), 7.23 – 7.33 (m, 1 H), 7.42 – 7.52 (m, 1 H), 7.78 (d, 1 H), 7.89 (br. s, 1 H), 8.42 – 8.51 (m, 3H), 8.56 (d, 1 H), 8.97 (S, 1 H), 9.32 (d, 1 H), 12.17 (s, 1 H).

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HITCHCOCK, Marion; MENGEL, Anne; MUeLLER, Thomas; BAeRFACKER, Lars; CLEVE, Arwed; BRIEM, Hans; SIEMEISTER, Gerhard; BONE, Wilhelm; FERNANDEZ-MONTALVAN, Amaury, Ernesto; SCHROeDER, Jens; MOeNNING, Ursula; HOLTON, Simon; PREUSSE, Cornelia; (165 pag.)WO2017/157991; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0,Some common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, 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.

N-(4-(ethylsulfonyl)benzyl)-4-(propylamino)benzamide (70 mg, 0.28 mmol) was added sequentially to a 50 mL vial.Bromomethylcyclopentane(45 mg, 0.28 mmol), anhydrous potassium carbonate (115 mg, 0.83 mmol),10 mL of acetonitrile, heated to reflux for 4 hours.The reaction was completed by TLC. Spin the solvent,Wash with saturated brine and dry over anhydrous sodium sulfate.Purification of petroleum ether by column chromatography: ethyl acetate 1:2,Obtained 30mg of white solid,The yield was 23.5%.

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

Reference:
Patent; Fudan University; Wang Yonghui; Qiu Ruomeng; Gong Juwen; Tian Jinlong; Huang Yafei; (65 pag.)CN109206346; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0, The chemical industry reduces the impact on the environment during synthesis 3814-30-0, name is (Bromomethyl)cyclopentane, I believe this compound will play a more active role in future production and life.

Example 4 7-(Cyclopentylmethyl)-3-propyl-[1,2,4]triazolo[4,3-a]pyrazin-8(7H)-one: To a solution of 3-propyl-[1 ,2,4]thazolo[4,3-a]pyrazin-8(7H)-one (200 mg, 1 .1 mmol) and (bromomethyl)cyclopentane (283 mg, 1 .35 mmol) in DMF (2 ml_) was added K2CO3 (310 mg, 2.2 mmol). The reaction was stirred at 60 C for 4 hours and then cooled to RT. The mixture was diluted with DCM (20 ml_) and washed with water (2×5 ml_). The organic layer was dried over Na2SO4 and evaporated. The crude product was washed with MeOH (2 ml_) to give 7-(cyclopentylmethyl)-3-propyl- [1 ,2,4]triazolo[4,3-a]pyrazin-8(7H)-one 120 mg (41 %) . 1H NMR (CDCI3, 400 MHz TMS): delta 6.91 (d, J=5.6 Hz, 1 H), 6.66 (d, J=5.6 Hz, 1 H), 3.89 (d, J=8.0 Hz, 2H), 2.94 (t, J=7.6 Hz, 2H), 2.37-2.31 (m, 1 H), 1 .92-1 .86 (m, 2H), 1 .73-1 .68 (m, 4H), 1 .63-1 .56 (m, 2H), 1 .32-1 .27 (m, 2H), 1 .04 (t, J=7.4 Hz, 3H). LCMS (MH+): m/z = 261 .1 , tR (minutes, Method 3) = 2.41

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

3814-30-0, name is (Bromomethyl)cyclopentane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of (Bromomethyl)cyclopentane

General procedure: Potassium carbonate (791 mg, 5.7 mmol) was added to a solution of 3-iodoindazole (700 mg, 2.9 mmol) and 2-chloroethyl methyl ether (406 mg, 4.3 mmol) in ACN (20 mL) at rt. The reaction was heated to reflux overnight, and then was filtered and concentrated. The residue was purified by silica gel chromatography (15%-50% EtOAc/hexanes) to give 530 mg (63%) of the title compound as a light yellow oil. The title compounds were prepared from 5-fluoro-3-iodo-indazole and (bromomethyl)cyclopentane according to the procedure for Preparation 10A. [0365] 1-(cyclopentylmethyl)-5-fluoro-3-iodo-1H-indazole (72%) was isolated as the major isomer eluting first. 1H NMR (400 MHz, CDCl3): delta 1.25-1.32 (2H, m), 1.50-1.65 (6H, m), 2.48-2.56 (1H, m), 4.27 (2H, d, J=7.5 Hz), 7.09 (1H, dd, J=8.3, 2.3 Hz), 7.18 (1H, td, J=8.9, 2.4 Hz), 7.32 (1H, dd, J=9.1, 4.0 Hz). [M+H] calc’d for C13H14FIN2, 345. found 345. [0366] 2-(cyclopentylmethyl)-5-fluoro-3-iodo-2H-indazole (18%) was isolated as the minor isomer eluting second. 1H NMR (400 MHz, CDCl3): delta 1.33-1.42 (2H, m), 1.56-1.73 (6H, m), 2.62-2.70 (1H, m), 4.41 (2H, d, J=7.6 Hz), 7.00 (1H, dd, J=8.8, 2.4 Hz), 7.09 (1H, td, J=9.2, 2.4 Hz), 7.65 (1H, dd, J=9.3, 4.5 Hz). [M+H] calc’d for C13H14FIN2, 345. found 345.

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Quanticel Pharmaceuticals, Inc.; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennen; US2014/171432; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 3814-30-0, 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. 3814-30-0, name is (Bromomethyl)cyclopentane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1-9-1 Preparation of N-(cyclopentylmethyl)-2-[1 -(cyclopentylmethyl)-1 H-indazol-3-yl]-5- methoxypyrimidin-4-amine 610 mg 2-(1 H-indazol-3-yl)-5-methoxypyrimidin-4-amine (2.5 mmol, 1 .0 eq.) was dissolved in 4 mL DMF and treated with 1 1 1 mg sodium hydride (60 %, 2.9 mmol, 1 .1 eq.) at room temperature under Argon atmosphere. It was stirred for 15 minutes, then the 93 mg Tetra-n-butylammoniumiodid (0.25 mmol, 0.1 eq.) was added and the mixture was cooled down to 0. 453 mg (bromomethyl )cyclopentane (2.9 mmol, 1 .1 eq), dissolved in 1 mL DMF, was added dropwise. It was stirred in the ice bath for 10 minutes and at room temperature for 2 days. The reaction mixture was diluted with dichloromethane and water, extracted three times with dichloromethane. The collected organic layers washed once with water and brine, filtered through a silicone coated filter and concentrated in vacuo. The crude product was treated with hexane and stirred. The unsolved residue was filtered off. The residue was treated with Methanol and stirred. The unsolved residue was filtered off: 375 mg, 99% pure, 1 .2 mmol, 45%. 1 H-NMR (400 MHz, DMSO-d6) delta [ppm] = 1 .26 – 1 .40 (m, 2H), 1 .44 – 1.72 (m, 6H), 2.53 – 2.58 (m, 1 H), 3.90 (s, 3H), 4.37 (d, 2H), 6.87 (br. s, 2H), 7.16 – 7.24 (m, 1 H), 7.35 – 7.44 (m, 1 H), 7.70 (d, 1 H), 8.00 (s, 1 H), 8.58 (d, 1 H).

The synthetic route of (Bromomethyl)cyclopentane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HITCHCOCK, Marion; MENGEL, Anne; MUeLLER, Thomas; BAeRFACKER, Lars; CLEVE, Arwed; BRIEM, Hans; SIEMEISTER, Gerhard; BONE, Wilhelm; FERNANDEZ-MONTALVAN, Amaury, Ernesto; SCHROeDER, Jens; MOeNNING, Ursula; HOLTON, Simon; PREUSSE, Cornelia; (165 pag.)WO2017/157991; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary