Month: December 2020

Synthetic Route of 51554-93-9,Some common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, molecular formula is C14H21Br, 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 3-neck round-bottomed flask equipped with a thermometer and a condenser was flame-dried and flushed with Ar. The flask was then charged with Mg0 (1.1 eq.), a single I2 crystal and another vacuum/Ar cycle was performed. Et2O (C=0.65M) was added resulting in a bright orange suspension of Mg0 pellets. Phenyl octyl bromide (1.0 eq.) was then added in one portion and the suspension was heated via a heatgun until the internal temperature reached 32C and stabilized for 5-10s, indicating that the Grignard formation had started. The reaction was stirred at rt until disappearance of the starting material by 1H NMR analysis (e.g.?1h). (0031) The Grignard solution (3.0 eq., C=0.65M) was then syringed to another flask containing substrate (1.0. eq.) in dry Et2O (C=0.05M). The solution was stirred at rt until disappearance of the starting material by TLC analysis. Saturated aqueous NH4Cl solution was added and the aqueous layer was extracted x2 with EtOAc. The organic layers were collected, washed x1 brine, dried over Na2SO4, filtered, concentrated in vacuo.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-octylbenzene, its application will become more common.

Reference:
Article; Garsi, Jean-Baptiste; Sernissi, Lorenzo; Vece, Vito; Hanessian, Stephen; McCracken, Alison N.; Simitian, Grigor; Edinger, Aimee L.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 217 – 242;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 67344-77-8, 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. 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromo-N-methylbenzylamine (12) (400 mg, 2 mmol), copper iodide (15.2 mg, 0.08 mmol) and dichlorobis(triphenylphosphine)palladium (II) (28 mg, 0.04 mmol) in DMF (3 mL) was added phenylacetylene (244.8 mg, 2.4 mmol) and triethylamine (556 uL, 4 mmol). The reaction vessel was flushed with argon, and the reaction mixture heated in the microwave for 5 minutes at 110¡ã C. The volatiles were removed in vacuo, ethyl acetate was added, and the organic solution washed successively with saturated NaHCO3 (.x.1), water (.x.1), brine (.x.1) and then extracted with 1N HCl. The acidic solution was basified to pH 9.0 with 1M NaOH, and then re-extracted with ethyl acetate, dried over magnesium sulfate and concentrated. Compound 13 was used without further purification. HPLC-MS tR=1.24 min (UV254 nm); mass calculated for formula C16H15N 221.1, observed LCMS m/z 222.1 (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, 1-(3-Bromophenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schering Corporation; US2007/129378; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 74586-53-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74586-53-1 name is 3-Bromo-5-methylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1 : A solution of 3-bromo-5-methylaniline (162.5 g, 873.66 mmol) in 1,4- dioxane (2 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (182 g, 994.54 mmol) and methanesulfonic acid (97.5 g, 1.02 mol) were added sequentially. The resulting solution was heated to reflux overnight. The resulting mixture was cooled and concentrated in vacuo. The residue was diluted with 2 L of water, then adjusted to pH 7-8 with aqueous saturated sodium bicarbonate solution, followed by extraction with EtOAc (2×2 L). The organic layers were combined, washed with water (2x 2 L), dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-(3-bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS ESI calc’d for Ci2H10BrF3 3 [M + H]+ 332, 334, found 332, 334. NMR (400 MHz, CDCI3): delta 8.68 (d, J= 4.9 Hz, 1 H), 7.79 (s, 1 H), 7.33-7.23 (m, 2 H), 7.10-7.06 (m, 2 H), 2.36 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; HAIDLE, Andrew, M.; KNOWLES, Sandra Lee; KATTAR, Solomon, D.; DESCHENES, Denis; BURCH, Jason; ROBICHAUD, Joel; CHRISTOPHER, Matthew; ALTMAN, Michael, D.; JEWELL, James, P.; NORTHRUP, Alan, B.; BLOUIN, Marc; ELLIS, John, Michael; ZHOU, Hua; FISCHER, Christian; SCHELL, Adam, J.; REUTERSHAN, Michael, H.; TAOKA, Brandon, M.; DONOFRIO, Anthony; WO2013/192098; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 5469-19-2, name is 1-Bromo-2,4,5-trimethylbenzene, 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 5469-19-2, COA of Formula: C9H11Br

Bromo-2,4,5-trimethyl-benzene (1) (2.64 g, 13.26 mmol), benezene- 1 ,4-diboronic acid (3) (1.00 g, 6.03 mmol) and a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.08 mmol) were added into a two-necked flask fitted with an Allihn condenser. The system was degassed and refilled with nitrogen three times. Then, 60 mL of distilled THF was injected, followed with an aqueous solution of potassium carbonate (0.15 g, 20 mL). After stifling at 85 C for 24 h, the mixture was extracted with DCM. The organic layer was collected and washed with deionized water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure, and the crude product was purified by silica gel column chromatography using hexanelDCM (5/1, v/v) as eluent. A white powder of TPh-TM was obtained in 75.3% yield (1.42 g, 4.52 mmol).

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; THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY; TANG, Benzhong; ZHANG, Haoke; (64 pag.)WO2018/137558; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 6627-78-7, 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. 6627-78-7, name is 1-Bromo-4-methylnaphthalene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 100 ml three-necked flask, compound 4”’ (10 mmol, 2.48 g) and THF (50 ml) were added, and n-butyllithium (11 mmol, 1.6 M, 6.88 ml) was slowly added dropwise under nitrogen atmosphere at -78C. The reaction was carried out at -78C for 2 hours, and then 5 ml of a THF solution of triisopropyl borate (15 mmol, 3.03 g) was slowly added dropwise to the reaction system. After the addition was completed, the mixture was slowly warmed to room temperature and stirred overnight. After the disappearance of the TLC test material, the reaction was completed. reaction. The mixture was quenched with dilute hydrochloric acid (20%, 20 ml), stirred at room temperature for 3 hours, then extracted with ethyl acetate (50 ml*3), and the combined organic phases were washed with saturated brine (100 ml*3) and dried over anhydrous sodium sulfate. The organic phase was concentrated and purified by column chromatography to give compound 3”’ (7.8 mmol, 1.45 g, 78%).

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, 1-Bromo-4-methylnaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu Ailikang Pharmaceutical Co., Ltd.; Chen Lei; Xing Xiaolan; Liu Yuxian; Lu Pingbo; (12 pag.)CN107814795; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 703-91-3, name is 5-Bromo-2-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Bromo-2-(trifluoromethyl)aniline

Pd(dppf)Cl2 (613 mg, 0.84 mmol) was added to a mixture of 5-bromo-2- (trifluoromethyl)aniline (Int 25a) (2.00 g, 8.37 mmol), cyclopropylboronic acid (929 mg, 12.56 mmol) and Na2CO3(1.77 g, 16.70 mmol) in dioxane (25 mL) and the mixture was stirred at 90 C overnight. The mixture was concentrated to dryness and the residue was purified by column chromatography (0-2% EtOAc in PE) to give the title compound as yellow oil.

The synthetic route of 703-91-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; DEUSCHLE, Ulrich; ALBERS, Michael; HOFFMANN, Thomas; (64 pag.)WO2018/141855; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 34950-82-8, These common heterocyclic compound, 34950-82-8, name is 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, 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.

To a solution of 7-bromo-3, 4-dihydro-2H-pyrido [3, 2- b] [l,4]oxazine (549 mg, 2.55 mmol) in DMF(dry) (10 rtiL) was added 60% NaH in oil (123 mg, 3.06 mmol) at 0C. The mixture was stirred at 0C under N2 for 10 min. 1- ( chloromethyl ) -2- . . (methoxymethyl ) benzene (523 mg, 3.06 mmol) was added to the mixture at 0C. The mixture was stirred at room temperature under N2 overnight. The mixture was quenched with water at 0C and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 5% – 50% EtOAc in hexane) to give the title (3288) compound (660 mg, 1.890 mmol, 74.0%) as white solids. (3289) MS (ESI+), found 349.1 (M+H) (3290) 1H NMR (300 MHz, CDC13) 5:3.28-3.33 (2H, m), 3.35 (3H, s) , (3291) 4.11-4.20 (2H, m) , 4.48 (2H, s) , 4.89 (2H,- s), 7.08 (1H, d, J = 2.3 Hz), 7.18-7.31 (3H, m) , 7.33-7.41 (1H, m) , 7.79 (1H, d, J = 1.9 Hz)

The synthetic route of 34950-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; SHIOKAWA, Zenyu; YUKAWA, Tomoya; IMADA, Takashi; NEGORO, Nobuyuki; ODA, Tsuneo; SASAKI, Satoshi; NARA, Yoshi; SUZUKI, Shinkichi; SATO, Ayumu; ISHII, Naoki; SHIBUYA, Akito; NAKAGAWA, Yasuo; COLE, Derek; GIBSON, Tony; IVETAC, Anthony; SWANN, Steve; TYHONAS, John; (472 pag.)WO2018/30550; (2018); 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 1647-23-0 as follows. Computed Properties of C6H13Br

To a mixture of 2-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4,6-bis(trifluoromethyl)- 2H-pyrazolo[3,4-d]pyrimidin-3-amine (100 mg, 0.21 mmol, 1 equiv), l-bromo-3,3- dimethylbutane (69.3 mg, 0.42 mmol, 2 equiv) in CH3CN (3.0 mL) was added potassium iodide (KI; 34.9 mg, 0.21 mmol, 1 equiv) and K3P04 (89.2 mg, 0.42 mmol, 2 equiv). The dark mixture was heated at 60 C for 5 h. The cooled mixture was diluted with EtOAc and washed with 0 (10 mL). The organic phase was concentrated in vacuo to give a residue, which was purified by preparative TLC to give the title compound (23 mg, 19.6%) as a yellow solid: ]H NMR (300 MHz, CDC13) delta 7.84 (s, 2H), 5.20 (br s, 1H), 2.91 – 2.84 (m, 2H), 1.46 – 1.41 (m, 2H), 0.77 (s, 9H); ESIMS m/z 568 [(M+H)]+.

According to the analysis of related databases, 1647-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; POBANZ, Mark A.; DENT, William Hunter; BENKO, Zoltan L.; ERICKSON, W. Randal; GENG, Chaoxian; WATSON, Gerald B.; SPARKS, Thomas C.; PATNY, Akshay; WO2014/126580; (2014); 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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3BrF2O2

To a cold solution of 5-bromo-2,2-difluorobenzo[dl[1,3ldioxole (5.75 mL, 42.2 mmol) in tetrahydrofuran (80 mL) was added a 2.0 M solution of isopropylmagnesium chloride in tetrahydrofuran (28.1 mL, 56.1 mmol) within 5-10 minutes while maintaining the temperature inthe range of 10-20 C. The reaction mixture was stirred at the same temperature for another 15 minutes and then allowed to attain room temperature with continued overnight stirring. The reaction mixture was cooled with an ice bath, triisopropyl borate (12.74 mL, 54.9 mmol) was added dropwise over 2 minutes, and stirring at room temperature was continued for 30 minutes. The reaction mixture was cooled to 10 C and 10% H2504 solution (50 mL) was added slowlywhich resulted in a slight exotherm to 20 C. After stirring for 15 minutes, the mixture was partitioned between water and ethyl acetate, and the combined organic extracts were washed with saturated NaHCO3 solution. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in 100 mL of tert-butyl methyl ether and cooled to 0 C. 30% Hydrogen peroxide solution in water (5.39 mL, 52.7 mmol) wasadded slowly, followed by water (60 mL), and the mixture was stirred overnight while warming up to ambient temperature. The reaction mixture was diluted with ethyl acetate and washed twice with sodium thiosulfate solution and brine. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated, and the residue was purified on silica gel (0-50% ethyl acetate in heptane) to give 6.43 g of the title compound as an amber oil. ?H NMR(400 MHz, DMSO-d6) oe ppm 9.75 (s, 1H), 7.12 (d, J = 8.7 Hz, 1H), 6.75 (d, J = 2.4 Hz, 1H),6.52 (dd, J = 8.7, 2.5 Hz, 1H). MS (ESI-) m/z 173.1 (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; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; TONG, Yunsong; XU, Xiangdong; ZHANG, Qingwei, I.; SWEIS, Ramzi, Farah; DART, Michael, J.; (184 pag.)WO2019/90078; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 58534-95-5, name is 3-Bromo-2-fluoroaniline, 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 58534-95-5, category: bromides-buliding-blocks

To a solution of 3-bromo-2-fluoro-phenylamine (1.10 g, 5.67 mmol) in DCM (50 mL) was added pyridine (0.68 mL, 8.51 mmol), 3-chloro-4-methoxy-benzenesulfonyl chloride (1.37 g, 5.70 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHC03, saturated aqueous NH4CI, brine and dried over Na2S04. The organic solvent was removed under reduce pressure and the crude triturated with Et2O to give the title compound (1.63 g) as a white solid. HPLC (254 nm): Rt: 5.74 min. HRMS (ESI) calcd for C13H10BrCIFNO3S [M+Na]+ 415.9129, found 415.9135. 1H NMR (600 MHz, DMSO-d6) delta ppm: 3.93 (s, 3 H) 7.10 (td, J=8.10, 1.19 Hz, 1 H) 7.22 – 7.25 (m, 1 H) 7.31 (d, J=8.79 Hz, 1 H) 7.47 – 7.52 (m, 1 H) 7.66 (dd, J=8.70, 2.29 Hz, 1 H) 7.74 (d, J=2.38 Hz, 1 H) 10.37 (s, 1 H).

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; NERVIANO MEDICAL SCIENCES S.R.L.; BINDI, Simona; CARENZI, Davide; MOTTO, Ilaria; PULICI, Maurizio; (83 pag.)WO2017/220477; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary