Category: 17247-58-4

Electric Literature of 17247-58-4, These common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, 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.

A solution of 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7g (91 mmol) of sodium iodide in 150 mL of acetone wasrefluxed overnite and then cooled to rt. The inorganic solids were filtered off and the acetone and cyclopropylcarbinyl iodide (8.41g, 46%) distilled off at ambient and 150 torr at 80 C, respectively. A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30mL of anhydrous diethyl ether(Et20) cooled to-78 C was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyl lithium in cyclohexanes and the solution was stirred for 5 min. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110mL of hexanes cooled to-78 C, the mixture warmed to rt over 1 h and was then carefully concentrated in vacuo. This mixture was redissolved inEt20, washed once with some ice-cold water, dried(MgS04) and concentrated carefully. This mixture was redissolved in 30mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stirovernite. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount ofCH2Cl2 in hexanes with 1-2 drops of MeOH to afford 1.39 g(42%) of cyclobutyl carbinylsulfonamide as a whitesolid.’H NMR(CDCI3) 1.81-2. 03 (m, 4H), 2.14-2. 28 (m, 2H), 2.81-2. 92 (m,1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 3C NMR (CD3)8 19.10, 28.21, 30.64, 60.93 ; MS m/e 148(M-l)-. time: 1.73, method B), 818 (M++H).

Statistics shows that (Bromomethyl)cyclobutane is playing an increasingly important role. we look forward to future research findings about 17247-58-4.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99274; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 17247-58-4, A common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, molecular formula is C5H9Br, 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 13 (176 mg, 0.5 mmol, 1 equiv.), anhydrous K2CO3 powder (346 mg, 2.5 mmol, 5 equiv.), and the appropriate bromoalkane (0.75 mmol, 1.5 equiv.) in DMF (1 mL) was stirred 40 C for 14 h. The mixture was poured into H2O (50 mL), and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (10 mL), dried (MgSO4), and the solvent evaporated. The crude products were purified by flash chromatography eluting with CHCl3-MeOH (96:4) or recrystallized from isopropanol.

The synthetic route of 17247-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Banister, Samuel D.; Beinat, Corinne; Wilkinson, Shane M.; Shen, Bin; Bartoli, Cecilia; Selleri, Silvia; Da Pozzo, Eleonora; Martini, Claudia; Chin, Frederick T.; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 392 – 400;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 17247-58-4,Some common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, molecular formula is C5H9Br, 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 stirred solution of the ketimime 1a’ (50 g, 187.1 mmol, available from Aldrich Chemical Company, Milwaukee, Wis.) under N2 in dry THF (400 mL) was cooled to -78 C. and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv.) in THF. The reaction mixture was warmed to 0 C. and stirred for 1 h and treated with bromomethylcyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et2O (300 mL) and treated with aq. HCl (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et2O (1 L). The aqueous layer was made basic to pH 12-14 with aq. NaOH (50%) and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give pure amine (1b’, 18 g) as a colorless oil.

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

Reference:
Patent; Schering Corporation; US2006/276405; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 17247-58-4, The chemical industry reduces the impact on the environment during synthesis 17247-58-4, name is (Bromomethyl)cyclobutane, I believe this compound will play a more active role in future production and life.

Example 1268: 2-(5-Chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)- 3-cyclobutylpropanoic acid Step lEthyl 2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)- 3- cyclobutylpropanoate Ethyl 2-(5-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)acetate (0.6g, 0.49 mmol) was dissolved in anhydrous DMF (3OmL), NaH (60% wt. in paraffin oil, 0.039 g, 1.69 mmol) was added at 00C. The reaction mixture was stirred for 30 min at room temperature and cyclobutylmethyl bromide (0.223 g, 1.49 mmol) was added drop wise at 0 0C. The reaction mixture was stirred an additional Ih at 0 0C and saturated NH4CI solution (1OmL) was added. The reaction mixture was extracted with EtOAc (3x20mL) and the combined organic phases were washed with water (3x20mL) and brine (2OmL), and dried over MgStheta4 The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography to yield ethyl 2-(5-chloro-6- (2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-3-yl)- 3-cyclobutylpropanoate (0.25 g) as a colorless liquid.

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)cyclobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2009/86277; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 17247-58-4, The chemical industry reduces the impact on the environment during synthesis 17247-58-4, name is (Bromomethyl)cyclobutane, I believe this compound will play a more active role in future production and life.

Step 2: (3aS,4S,65′)-2-[(1S)-1-chloro-2-cyclobutylethyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole (intermediate 2)To Mg (13.60 g, 560 mmol) in THF (650 mL) was added DIBAL (1 M in toluene, 9.1 mL, 9.1 mmol) under N2, and the mixture was stirred for 30 min at room temperature. Intermediate 2 (40.6 mL, 360 mmol) was then added dropwise below 40 C. and the reaction mixture was stirred at room temperature for 2.5 h. After cooling to -78 C., the solution was transferred to a solution of intermediate 1 (70 g, 0.267 mol) in THF (400 mL) at -78 C. under N2 protection and the resulting mixture was stirred for 45 min. ZnCl2 (1 M in Et2O, 750 mL, 750 mmol) was then added in one portion, the mixture was allowed to warm to room temperature and stirred overnight. To the reaction mixture were added ethyl acetate (800 mL) and sat. NH4Cl (350 mL), the mixture was stirred for 1 h and the organic layer was washed with water (300 mL), brine (300 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (petroleum ether: ethyl acetate=20:12:1) to afford intermediate 2 (65 g, 82% yield) as a colorless oil.

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)cyclobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2010/81633; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, belongs to bromides-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 17247-58-4, Product Details of 17247-58-4

Synthesis 9(f)Chemical Formula C16H17NO4 Chemical Formula C21H2JNO4 Chemical Formula C21H27NO4 Exact Mass 287 1 Exact Mass 355 2 Exact Mass 357 2 Molecular Weight 287 3 Molecular Weight 355 4 Molecular Weight 357 4Noroxymorphone N-(CBM)-Noroxymorphone Nalbuphine N-fcyclobutylmethy?-NoroxymorphoneStep 1: Synthesis of N-(cvclobutylmethyl)-Noroxymorphone from Noroxymorphone[0097] Noroxymorphone (1.59 g, 5.5 mmol), potassium carbonate (0.61 g, 6.1 mmol), potassium iodide (0.46 g, 2.8 mmol), and dimethyl acetamide (10 mL) were added into a round bottom flask. Bromomethylcyclobutane (0.82 g, 5.5 mmol, 0.62 mL) was added. The reaction was stirred for 7 days at room temperature. At that time, bromomethylcyclobutane (0.82 g, 5.5 mmol, 0.62 mL) was added. The reaction was stirred for an additional 7 days. HPLC analysis indicated that the noroxymorphone was consumed. Distilled water (50 mL) was added and stirred at room temperature for 6 hours. An off-white precipitate formed, which was removed by filtration. The solid was washed with distilled water (25 mL), then slurried for 24 hours in acetonitrile (25 mL). Filtration, washing the solid with acetonitrile (10 mL), and drying at room temperature under vacuum for 24 hours yielded N-(cyclobutylmethyl)-noroxymorphone (1.43 g, 73% yield) as a tan solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Bromomethyl)cyclobutane, and friends who are interested can also refer to it.

Reference:
Patent; MALLINCKRODT INC.; WO2008/137672; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 17247-58-4, These common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, 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.

[0079] Step G: l-[2-(2,4-Dichloro-phenyl)-ethyl]-8-(3-methoxy-phenyl)-l,3- diaza-spiro[4.5]decane-2,4-dione 86 (0.52 g, 1.16 mmol), bromomethylcyclobutane (0.175 mL, 1.56 mmol) and potassium carbonate (0.32 g, 2.32 mmol) in dry DMSO (5.0 mL) are stirred for 3 h at 500C. The mixture is cooled to rt, diluted with water and extracted with DCM (3x). The combined extracts are washed with 1 N HCl, H2O (3x) and brine, dried over MgSO4, and concentrated to afford 3-cyclobutylmethyl-l-[2-(2,4-dichloro-phenyl)-ethyl]-8- (3-methoxy-phenyl)-l,3-diaza-spiro[4.5]decane-2,4-dione 87 (0.65 g, quant.) as a clear, thick oil: MS calcd. for C28H33Cl2N2O3 (MH-H+) 515.1, found 515.1; 1H-NMR (400 MHz, CDCl3) delta = 7.40 (d, J= 1.7 Hz, IH), 7.21 (m, 3H), 6.88 (d, J = 7.9 Hz, IH)5 6.83 (t, J= 2.2 Hz, IH)5 6.75 (dd, J= 2.2, 7.9 Hz, IH), 3.80 (s, 3H)5 3.54 (d, J= 7.4 Hz5 2H), 3.41 (t, J= 7.2 Hz5 2H), 3.13 (t, J= 7.2 Hz, 2H)5 2.71 (septet, J= 7.7 Hz, IH), 2.38 (m, 3H), 2.02 (m5 2H), 1.88 (m, 2H)5 1.77 (m, 6H)5 1.62 (m, 2H).

The synthetic route of 17247-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/87448; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 17247-58-4 as follows. Recommanded Product: (Bromomethyl)cyclobutane

4e. Preparation of Cyclobutylcarbinylsulfonamide A solution of 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7 g (91 mmol) of sodium iodide in 150 mL of acetone was heated to reflux overnight and then cooled to room temperature. The inorganic solids were removed by filtration and the acetone and cyclopropylcarbinyl iodide (8.41 g, 46%) were removed by distillation (ambient temperature and 150 torr at 80 C., respectively). A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30 mL of anhydrous diethyl ether cooled to -78 C. was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyllithium in cyclohexanes and the solution was stirred for 5 minutes. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110 mL of hexanes cooled to -78 C., the mixture warmed to room temperature over 1 hour and was then carefully concentrated in vacuo. This mixture was redissolved in diethyl ether, washed once with some ice-cold water, dried (MgSO4), filtered, and concentrated carefully. This mixture was redissolved in 30 mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stir overnight. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount of dichloromethane in hexanes with 1-2 drops of methanol to provide 1.39 g (42%) of the desired product as a white solid. 1H NMR (CDCl3) delta 1.81-2.03 (m, 4H), 2.14-2.28 (m, 2H), 2.81-2.92 (m, 1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 13C NMR (CDCl3) delta 19.10, 28.21, 30.64, 60.93. MS m/e 148 (M-H)-.

According to the analysis of related databases, 17247-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 17247-58-4, The chemical industry reduces the impact on the environment during synthesis 17247-58-4, name is (Bromomethyl)cyclobutane, I believe this compound will play a more active role in future production and life.

A stirred solution of ketimine 2a (50 g, 187.1 mmol) under N2 in dry THF (400 mL) was cooled to -78 C. and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv.) in THF. The reaction mixture was warmed to 0 C. and stirred for 1 h and treated with bromomethyl cyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et2O (300 mL) and treated with aq. HCl (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et2O (1 L). The aqueous layer was made basic to pH 12-14 with NaOH (50% aq.) and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the pure amine (2b, 18 g) as a colorless oil.

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)cyclobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; US2005/197301; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

17247-58-4, name is (Bromomethyl)cyclobutane, 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. COA of Formula: C5H9Br

4-(4,455-tetramethyl-1 3,2-dioxaborolan-2-yl)-1H-pyrazole (2.00 g, 10.3 mmol), (bromomethyl)cyclobutane (3.5 ml, 31 mmol) and potassium carbonate (5.70 g, 41 .2 mmol) were stirred in N,N-dimethylacetamide (16 ml) overnight at 80C. The mixture was concentrated under reduced pressure, the residue was dissolved with ethyl acetate, and the resulting solution was washed three times with water. The combined organic layers were dried over a silicone filter and concentrated under reduced pressure to give 2.40 g (90 % purity, 80 % yield) of the title compound. LC-MS (Method 2): Rt = 1 .21 min; MS (ESIpos): m/z = 263 [M+H]+ 1H-NMR (400MHz, DMSO-d6): _ [ppm]= 1.24 (s, 12H), 1 .67 – 1 .99 (m, 6H), 2.67 – 2.77 1H), 4.12 (d, 2H), 7.55 (s, 1H), 7.90 (d, 1H).

The synthetic route of 17247-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LEFRANC, Julien; MENGEL, Anne; SCHULZE, Volker; CHRIST, Clara; PRINZ, Florian; WENGNER, Antje, Margret; STOeCKIGT, Detlef; BOeMER, Ulf; BADER, Benjamin; (288 pag.)WO2017/207534; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary