Tag: M.W=100-200

Synthetic Route 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

Adding a certain compound to certain chemical reactions, such as: 2695-48-9, name is 8-Bromo-1-octene, 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 2695-48-9, Quality Control of 8-Bromo-1-octene

[00294] (Z)-8-bromo-l-chloro-l-octene (5): Following the general procedure, a solution of Mo-4 in benzene (0.1 M, 30 mu, 3.0 muiotaetaomicron, 3 mol %) was transferred by syringe to an oven- dried vial containing Z-l,2-dichloroethylene (48.5 mg, 0.5 mmol, 5.00 equiv), 8-bromo-l-octene (19.1 mg, 0.1 mmol, 1.00 equiv) and benzene (470 mu). The resulting solution was allowed to stir for 4 hours at 22 C. The reaction was quenched by addition of wet CDCI3 and analysis of the unpurified mixture revealed 90% consumption of 8-bromo-l-octene. The resulting orange oil was purified by silica gel chromatography (100%) hexanes) to afford 5 (17.4 mg, 0.0771 mmol, 77 % yield) in >98:<2 Z:E ratio as colorless oil. 1H NMR (400 MHz, CDC13): Z-isomer (major): delta 6.02 (1H, dt, J= 7.2, 1.6 Hz), 5.74 (1H, q, J= 7.2 Hz), 3.41 (2H, t, J= 6.8 Hz), 2.23 (2H, qd, J = 7.2, 1.6 Hz), 1.86 (2H, m), 1.49-1.31 (6H, m). At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-1-octene, and friends who are interested can also refer to it. Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; TRUSTEES OF BOSTON COLLEGE; HOVEYDA, Amir H.; ZHANG, Hanmo; KOH, Ming Joo; SCHROCK, Richard Royce; (163 pag.)WO2016/73750; (2016); A1;,
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 10269-01-9, The chemical industry reduces the impact on the environment during synthesis 10269-01-9, name is (3-Bromophenyl)methanamine, I believe this compound will play a more active role in future production and life.

(4?-(Trifluoromethyl)biphenyl-3-yl)methanamine. A 1 00-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with (3- bromophenyl)methanamine (570 mg, 3.0 mmol), 4-(trifluoromethyl)phenylboronic acid (558 mg, 3.0 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol), K3P04 (1.91 g, 9.0 mmol), DME (30 mL) and H20 (6 mL). The system was subject to 3 cycles of vacuum/argon flush and heated at reflux for overnight. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:20 MeOH/CH2C12 to afford the title compound (640 mg, 85%) as brown solid. MS-ESI: [M+H] 252.1.

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, (3-Bromophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9, Quality Control of 5-Bromo-2-methylaniline

4-Chlorophenylboronic acid (20.2 g, 0.13mol) and tetrakis(triphenylphosphine)palladium (0) (3.7g, 0.003 mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1 ,2- dimethoxyethane (200 ml). After stirring the reaction mixture for 15 minutes at 200C, a solution of 20% aqueous sodium carbonate (300ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 5-(4- chlorophenyl)-2-methylaniline (21.0 g).

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; SYNGENTA PARTICIPATIONS AG; WO2008/110307; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 51437-00-4, 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 51437-00-4 as follows.

To a solution of diisopropylamine (1.77g, 17.5 mmol, 1.1 eq) in THF (20 mL) was added n-BuLi (7.3 mL, 2.4 M in THF, 17.5 mmol, 1.1 eq) at -78C under N2. The mixture was stirred at -78C for lh, then a solution of 4-bromo-l-fluoro-2 -methyl-benzene (3 g, 15.8 mmol, 1.0 eq ) in THF (20 mL) was added dropwise. The reaction was stirred a further 2h at -78C then C02 gas was bubbled into the mixture for 30 min. The reaction was quenched by addition of water and acidified to pH 3 by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2S04), filtered and evaporated in vacuo. The residue obtained was purified by chromatography to give the title compound as a white solid (697 mg, 21 %).LC-MS : m/z 230.9, 232.9 [M-H]” HNMR (400 MHz, DMSO-d6) ? 7.94 – 7.59 (m, 2H), 2.26 (s, 3H)

According to the analysis of related databases, 51437-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 452-74-4, 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. 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

A degassed solution of 3-amino-furo[3,2-c]pyridine-2-carboxylic acid ethyl ester (300 mg, 1.46 mmol), 4-bromo-3-fluorotoluene (277 mul, 2.19 mmol), Pd2dba3 (67 mg, 0.073 mmol), Xantphos (84 mg, 0.15 mmol) and potassium phosphate tribasic (620 mg, 2.92 mmol) in toluene (10 ml) was heated at reflux under an argon atmosphere for 16 hours. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (Si-SPE, pentane: diethyl ether, gradient 100:0 to 75:25) to afford the title compound as a yellow solid (252 mg, 55%). LCMS (method B): Rx = 3.14 min, M+H+ = 315.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-fluoro-4-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application 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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3BrF2

Example 67; 6-fluoro-9-furan-3-yl-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride; (1) 3-bromo-2,6-difluorobenzoic acid; To a mixed solution of 1.6N solution of n-butyllithium in hexane (9.4 ml, 15.0 mmol) and tetrahydrofuran (20 ml) were successively added 2,2,6,6-tetramethylpiperidine (2.50 ml, 15.0 mmol) and 1-bromo-2,4-difluorobenzene (2.90 g, 15.0 mmol) at -78°C, and the mixture was stirred at -78°C for 1 hr. The pulverized dry ice (5 g) was added, and the mixture was stirred at -78°C for 2 hr. Saturated aqueous ammonium chloride solution (5 ml) was added to the reaction mixture, and the mixture was stirred at room temperature for 30 min. Water (10 ml) and 1N hydrochloric acid (30 ml) were added, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Hexane was added to the residue, and desired product (2.30 g, 64.6percent) was collected by filtration as a solid. 1H-NMR (CDCl3) delta; 6.91-6.97 (1H, m), 7.66-7.73 (1H, m).

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; Takeda Pharmaceutical Company Limited; EP2123644; (2009); 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. 6911-87-1, name is 4-Bromo-N-methylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 6911-87-1

To a microwave reaction vessel were added 2-aminopyridine-5-boronic acid pinacol ester (220 mg, 1.0 mmol), 4-bromo-N-methylaniline (184 mg, 1.0 mmol), 1,4-dioxane (4 mL) and 20% aq sodium carbonate (3 mL). Argon gas was bubbled through the solution for 5 min, then tetrakis(triphenylphosphine) palladium(O) (57 mg, 0.05 mmol) was added. The vial was sealed and heated in a microwave reactor for 30 min at 150 C. After cooling to rt, silica gel was added and the mixture was concentrated under reduced pressure. Purification by silica gel flash chromatography eluting with 1 :20 MeOH/ EtOAc gave 5-(4- (methylamino)phenyl)pyridin-2-amine (79 mg, 39%) as an off white solid. LC-MS (ESI) m/z 200 (M +H)+.

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; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; HOLLADAY, Mark, W.; LIU, Gang; XU, Shimin; WO2011/22473; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary