Tag: M.W=100-200

Electric Literature of 7073-94-1, These common heterocyclic compound, 7073-94-1, name is 1-Bromo-2-isopropylbenzene, 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.

tert-butyl 4-[2-[[(2,S)-l- methylpyrrolidin-2-yl]methoxy]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl]piperazine-l- carboxylate (200 mg, 462 umol), l-bromo-2-isopropyl-benzene (120 mg, 601 umol), CS2CO3 (452 mg, 1.39 mmol) and XPHOS PALLADACYCLE GEN 3 (78.3 mg, 92.5 umol) in toluene (4.00 mL) was de-gassed with N2 and then heated to 100 C for 10 hours under N2. Upon completion, the mixture was filtered and the filtrate was concentrated. The crude product was purified by silica gel chromatography eluted with EtOAc/MeOH= 50/1 to 5/1 to give tert-butyl 4-[7-(2-isopropylphenyl)-2-[[(2,S)-l-methylpyrrolidin-2-yl]methoxy]-6,8-dihydro-5H- pyrido[3,4-d]pyrimidin-4-yl]piperazine-l-carboxylate (84.6 mg, 134 umol, 28.9 % yield, 87.0 % purity) as a yellow solid. ES+APCI MS m/z 551.2 [M+H]+.

Statistics shows that 1-Bromo-2-isopropylbenzene is playing an increasingly important role. we look forward to future research findings about 7073-94-1.

Reference:
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
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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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H7Br

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (10 g, 54.63 mmol, 1.00 equiv) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 21.9 mL, 1.00 equiv) dropwise with stirring at -78C. The reaction mixture was stirred for 20 min at -78C. To the resulting mixture was then added a solution of 5-bromo-2-methylbenzaldehyde (1 1.4 g, 57.27 mmol, 1.05 equiv) in THF (10 mL) dropwise at -78C. The reaction mixture was stirred for 1 h at -78C. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (20: 1 PE/EA) to yield (5-bromo-2-methylphenyl)(1,2-dihydrocyclobutabenzen-4-yl)methanol as colorless oil. 1 H NMR (400 MHz, Chloroform-d) delta 7.83 (d, J = 2.2 Hz, 1H), 7.34 (dd, J = 8.0, 2.2 Hz, 1H), 7.17 (dd, J = 7.5, 1.5 Hz, 1H), 6.96 -7.07 (m, 3 H), 5.89 (s, 1H), 3.16 (s, 5 H), 2.15 (s, 3 H).

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
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Related Products of 556-96-7, 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. 556-96-7, name is 1-Bromo-3,5-dimethylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: CuI (0.05 mmol), aryl halide (0.5 mmol), Na3PO4 (0.5 mmol), 25-28% aqueous ammonia (1 mL), and PEG-400 (2 mL) were added to a sealed tube. The reaction mixture was stirred at 100 C (aryl iodides for 15 h and aryl bromides for 24 h) and then cooled to room temperature and extracted with diethyl ether (3 times). The combined organic phase was then dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The remaining residue was purified by column chromatography on silica gel to provide the desired aryl amines.

The synthetic route of 1-Bromo-3,5-dimethylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Junmin; Yuan, Tangjun; Hao, Wenyan; Cai, Mingzhong; Tetrahedron Letters; vol. 52; 29; (2011); p. 3710 – 3713;,
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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. 7051-34-5, name is (Bromomethyl)cyclopropane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (Bromomethyl)cyclopropane

THF (200 mL) was added to the reaction flask, Potassium carbonate (11.0 g, 0.08 mol) and 3-hydroxy-4-difluoromethoxybenzaldehyde (10.0 g, 0.053 mol) were added and the mixture was stirred at room temperature for 1 hour. Then, methyl bromocyclopropane (10.8 g, 0.80 mol) was added and TLC Hydroxy-4-difluoromethoxybenzaldehyde was dissolved and the reaction was quenched by addition of water (100 mL) and extracted with dichloromethane. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a brown oil 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (10.5 g, yield 82%, purity 93.9%, HPLC chromatogram shown in Figure 3), without purification can be directly used in the next step reaction

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 7051-34-5.

Reference:
Patent; Taicang Enkang Pharmaceutical Technology Co., Ltd.; Wang Xiang; Shang Muhong; Wang Li; Zhang Feng; Yu Su; Gong Yadong; (12 pag.)CN106883118; (2017); A;,
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Synthetic Route of 7051-34-5, These common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, 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.

Step 1 : A mixture of 4-hydroxybenzaldehyde (1.0 g, 8.19 mmol), (bromomethyl)cyclopropane (1.33 g, 9.83 mmol) and K2CO3 (2.26 g, 16.38 mmol) in DMF (10.0 mL, anhydrous) was stirred at 20 C for 12 hours. The solution was diluted with water (20 mL). The aqueous phase was extracted with ethyl acetate (60 mL chi 3). The combined organic phase was washed with brine (20 mL * 1 ), dried over anhydrous Na2SO4 , filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=10/1 , 1/1 ) to give 4-(cyclopropylmethoxy)benzaldehyde (1.3 g, 87% yield).

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

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;,
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Application of 1003-98-1,Some common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 an ice-cooled mixture of 2-bromo-4-fluoroaniline (25.0 g, 0.132 mol), ammonium thiocyanate (40.0 g, 0.525 mol) in acetic acid (180 mL) was added dropwise a solution of bromine (13.5 mL, 0.264 mol) in acetic acid (35 mL) over 1 h. After stirring at room temperature for 2 h, the yellow insoluble material was collected by filtration. The yellow cake was suspended in water, and the pH was adjusted to 11 by adding potassium carbonate. The insoluble material was collected again, and the cake was purified by flash column chromatography on silica gel (Hexane:AcOEt = 3:1) to give the title compound as a yellow solid (29.7 g, 91%). Mp 183-185 C. 1H NMR (400 MHz, DMSO-d6) delta 7.37 (1H, dd, J = 8.5, 2.4 Hz), 7.64 (2H, dd, J = 8.5, 2.4 Hz), 7.82 (2H, brs). 13C NMR (100 MHz, DMSO-d6) delta 107.5 (d, J = 27.8 Hz), 109.4 (d, J = 11.5 Hz), 116.0 (d, J = 26.8 Hz), 131.8 (d, J = 11.5 Hz), 147.7 (d, J = 1.9 Hz), 156.2 (d, J = 239.6 Hz), 166.8. IR (ATR) nmax 3079, 1634, 1539, 1452, 1394, 1319, 1208, 1099, 1057, 940, 847 cm-1. MS (EI) 246 (M+). HRMS (EI) calcd for C7H4BrFN2S (M+) 245.9304, found 245.9263.

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Watanabe, Daisuke; Kohno, Yasushi; Seto, Shigeki; Tetrahedron; vol. 72; 12; (2016); p. 1566 – 1572;,
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Application of 1798-85-2, 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. 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A Schlenk flask was charged with an appropriate amount of complex 2b (0.016mmol, 2.0mol%) and the corresponding bromo or iodo arene (0.77mmol). The flask was cycled with nitrogen and vacuum. Afterwards a THF solution of benzylzinc bromide (2.2mL, 1.1mmol, 0.5M in THF) was added. The flask was sealed and heated at 70C for 24h. After that time, the mixture was cooled, and dichloromethane and water were added. The aqueous layer was extracted with dichloromethane and the collected organic layers were washed with water and dried with Na2SO4. The coupling product was confirmed by GC-MS (with n-dodecane as internal standard) and NMR analysis. The analytical properties of the products are in agreement with literature data [6a,24].

The synthetic route of 1-Bromo-3-cyclopropylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Someya, Chika I.; Irran, Elisabeth; Enthaler, Stephan; Inorganica Chimica Acta; vol. 421; (2014); p. 136 – 144;,
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Reference 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.

Sodium sulfite (1.3 g; WAKO), ethanol (3.9 mL), and water (5.8 mL) were added to (bromomethyl)cyclobutane (0.8 mL; Ald), the resulting mixture was stirred at 100 C. for 2 hours, and the solvent was evaporated under reduced pressure. Toluene (10 mL), DMF (20 muL), and thionyl chloride (1.9 mL; TCI) were successively added to the residue, the resulting mixture was stirred at 110 C. for 5 hours, and the solvent was evaporated under reduced pressure. This residue was used instead of ethanesulfonyl chloride described in the step of Reference Example N-2 to give the title compound.

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; ASAHI KASEI PHARMA CORPORATION; US2010/261701; (2010); A1;,
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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 1073-06-9 as follows. COA of Formula: C6H4BrF

Add carbazole (2g, 11.93mmol) to a 100mL reaction flask.2-bromo-4-fluorobenzene (2g, 11.36mmol), potassium carbonate (3.14g, 22.73 mmol), DMSO (30mL),Under nitrogen protection, heat to 140 C for 4 hours.The reaction was monitored by TLC until the reaction was complete.Filter under reduced temperature and rinse the filter cake with ethyl acetate and water.The aqueous phase was separated, the organic layer was dried and concentrated, 100 mL of n-hexane was added, and sonication was performed for 2 minutes. A white solid was precipitated and filtered to obtain 1.3 g of intermediate M4.

According to the analysis of related databases, 1073-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gao Wenzheng; Du Qian; Zhang Chunyu; Ren Xueyan; (35 pag.)CN110407825; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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 1647-26-3, HPLC of Formula: C8H15Br

The title compound was prepared by General Method 2. p-tolylhydrazine hydrochloride (0.96g, 6.0mmol) was added to a vigorously stirred mixture of tetra-n-butylammonium chloride (84mg, 0.3mmol) in 50% aqueous sodium hydroxide (6mL) followed by 2-cyclohexylethyl bromide (1.26g, 6.6mmol). The mixture was heated at 60 0C (oil bath temp.) for 6h. After cooling to room temperature, water (20-3OmL) was added and the mixture extracted with chloroform (3 x 1OmL). The total extract was dried (sodium sulfate), evaporated in vacuo to give a dark oil (1.49g) which was chromatographed (45g of silica gel, eluted with dichloromethane) to give the product as a yellow-orange oil (0.68g, 2.93mmol, 48.8%).

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-2-cyclohexylethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; WO2009/120717; (2009); A2;,
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