Tag: M.W=200-300

Application of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, 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: To a flame dried, 3 times evacuated and argon purged 25mL Schlenk flask was added 4.6mmol of aryl bromide (2-bromo-9,9-dimethylfluorene, 9-bromoanthracene, and 1-bromo-4-methylnaphthalene) and a magnetic stir bar. The flask was then cooled to -78 C (dry ice/acetone bath) for 10min under argon (room temperature for phenylacetylide). Then 10mL of dry argon purged diethyl ether was added to the reaction and allowed to cool for another 10min. This was followed by 2.2mL (5.5 mmol) of n-butyllithium solution in diethyl ether. The reaction was allowed to stir for 30min to complete the halide-exchange reaction, at which time the reactions turned a yellow color and salt precipitates formed. Then 1 g (3.8mmol) of spirosiloxane I dissolved in 5mL of cooled dry argon purged diethyl ether was added by syringe to the reaction mixture and allowed to stir for an additional 2 h. The reaction was run till the yellow color subsided and was then quenched with excess Me3SiCl and allowed to stir cold for >30min before warming up. The reaction was then worked up by a quick water wash (2 times) to remove salts and then dried over MgSO4. The reaction was then filtered through Celite to remove salts and solvent removed in vacuo. Yellow-orange viscous oils were obtained. Characterization is given in tabular form in the text.

The synthetic route of 6627-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Furgal, Joseph C.; Laine, Richard M.; Bulletin of the Chemical Society of Japan; vol. 89; 6; (2016); p. 705 – 725;,
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Reference of 69272-50-0, These common heterocyclic compound, 69272-50-0, name is 3,6-Dibromobenzene-1,2-diamine, 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.

3,6-Dibromobenzene-1,2-diamine with round flask equipped with a condenser (compound 2-a) (1g) and phenanthrene-9,10-dione (0.8 g) after the into the respective acetate, 30mL ethanol and 30 after the injection, each mL, was added the temperature to 80 C, and reacted for 24 hours. If after the completion of the reaction through the methanol, the resulting solid filter using methanol to afford a yellow solid 10,13-dibromodibenzo [a, c] phenazine (compound C). (Yield: 68%).

Statistics shows that 3,6-Dibromobenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 69272-50-0.

Reference:
Patent; Pusan National University Industry-Academic Cooperation Foundation; Hwang, Do Hun; Kim, Ji Hun; Kim, Hee Woon; Im, Jong Min; (52 pag.)KR101495152; (2015); B1;,
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Synthetic Route of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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: tert-Butyl 3-bromo-5-(tert-butyl)benzoate (11a) n-Butyl lithium (7.2 mL, 18.0 mmol, 2.5M in THF) was added to a 100 mL flask under nitrogen atmosphere containing 9 mL of toluene at -10C. n-Butylmagnesium chloride (4.5 mL, 9.0 mmol, 2M in THF) was then added at such a rate to keep the temperature below -5C. The resulting milky slurry was aged at -10C for 30 min. To this slurry was added 1,3-dibromo-5-(tert-butyl)benzene (6.2 g, 21.2 mmol) dissolved in 20 mL of toluene. The rate of addition was such that the temperature did not increase above -5C. After addition was complete, the mixture was kept at -10C until the metal-halogen reaction was complete. A solution of di-tert-butyl dicarbonate (5.89 g, 27 mmol) in 7.5 mL of toluene was then charged such at a rate to keep the temperature below -5C. After the addition was complete, the mixture was kept at -10C until the aryl-Mg intermediate was completely consumed. The mixture was quenched by the addition of 40 mL of a 10% (w/w) aqueous solution of citric acid, which resulted in an exothermic generation of carbon dioxide. The phases were separated and the organic layer was washed with another 40 mL of citric acid solution. The organic extracts were then dried with MgSO4 and the solvents were removed at reduced pressure. Compound 11c was obtained as a brown oil (4.0 g, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-(tert-butyl)benzene, its application will become more common.

Reference:
Patent; Phenex Pharmaceuticals AG; EP2511263; (2012); A1;,
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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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2051-99-2

Intermediate A6 2-(4-isobutylphenyl)-6-methoxy-3.4-dihvdroisoquinolin-l(2H)-one vial, 6-methoxy-3,4-dihydroisoquinolin-l(2H)-one (0.25 g, 1.411 mmol) was dissolved in N-dimethylformamide (2.82 ml). To this was added l-bromo-4-isobutylbenzene (0.451 g, 2.116 mmol) and potassium carbonate (0.390 g, 2.82 mmol). The reaction mixture was flushed with nitrogen, charged with copper(I) iodide (0.161 g, 0.847 mmol) and heated to 150 C for 24 h. The reaction mixture was cooled to room temperature, quenched with water and extracted three times with dichloromethane. The organic layers were combined, passed through a phase separator and concentrated. The crude material was purified via silica gel chromatography using 0-75% ethyl acetate in heptanes to afford the desired product (190 mg, 0.614 mmol, 43.5 % yield) as a light orange solid. NMR (400 MHz, Chloroform-d) delta 8.12 (d, J = 8.7 Hz, 1H), 7.32 – 7.27 (m, 2H), 7.24 – 7.15 (m, 2H), 6.89 (dd, J = 8.7, 2.6 Hz, 1H), 6.77 – 6.65 (m, 1H), 3.96 (dd, J = 7.0, 6.0 Hz, 2H), 3.86 (s, 3H), 3.09 (t, J = 6.4 Hz, 2H), 2.50 (d, J = 7.1 Hz, 2H), 1.90 (dh, J = 13.5, 6.8 Hz, 1H), 0.94 (d, J = 6.6 Hz, 6H). LC MS (m/z, MH+): 310.4.

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 2051-99-2.

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
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Related Products of 1753-75-9,Some common heterocyclic compound, 1753-75-9, name is 5-Bromobenzo[c][1,2,5]thiadiazole, molecular formula is C6H3BrN2S, 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.

Benzo[1 ,2,5]thiadiazol-5-yl-(8-chloro-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-yl)-amine (“BIO”)100 mg (0.6 mmol) of 8-pyridin-3-yl-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine, mg (0.9 mmol) 5-bromo-2,1 ,3-benzothiadiazole, 68 mg (0.1 mmol) 9,9- dimethyl-4,5-bis(diphenylphosphino)xanthene , 578 mg (1.8 mmol) cesium carbonate and 34 mg bis(dibenzylideneacetone)palladium are dissolved in 1 ml dioxane and stirred at 90 C for 14 h. HPLC and LC-MS analysis show formation of the product (LCMS (method C): mass found (M+H+, 303), HPLC (method D) Rt (min): 3.07.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromobenzo[c][1,2,5]thiadiazole, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; BURGDORF, Lars; SCHULTZ, Melanie; DEUTSCH, Carl; COMAS, Horacido; SWINNEN, Dominique; POMEL, Vincent; GAILLARD, Pascale; HODOUS, Brian; WO2012/25186; (2012); A1;,
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Electric Literature of 30273-40-6, 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. 30273-40-6, name is 4-Bromo-2,5-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 25-mL 3-necked round-bottom flask under N2 atmosphere, was placed 4-allyl- 1 – methyl- 1 H-pyrazole-5 -carboxylic acid (0.843 g, 5.07 mmol, 1 equiv), 4-bromo-2,5- dimethylaniline (1.0 g, 5.00 mmol, 0.99 equiv), HATU (2.9 g, 7.63 mmol, 1.50 equiv), DIEA (1.3 g, 10.15 mmol, 2 equiv) and DMF (10 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and the resulting solution was extracted with ethyl acetate. The combined organic layer was concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10) to give 1.2 g (67.93%) oftitle compound as a white solid. LC-MS: (ES, m/z): [M+H]+ 348.

The synthetic route of 4-Bromo-2,5-dimethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; ASWAD, Fred; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; HATA, Yujiro; SUTTON, JR., James Clifford; (0 pag.)WO2019/236766; (2019); A1;,
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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. 102169-44-8, name is 4-Bromo-5-methylbenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Bromo-5-methylbenzene-1,2-diamine

4-bromo-5-methylbenzene-1,2-diamine (5 · 0 g, 23.6 mmol) and Isobutyraldehyde (2.13, 28.4 mmol) was dissolved in 75 ml of ethanol and cobalthydroxide (220 mg, 2.4 mmol) blended. The reaction mixture was stirred overnight, opened the lid, filtered and concentrated under reduced pressure to dryness. The residue was by chromatography through silica gel (Biotage Isolera, SNAP 340 g, eluent: hexane / ethyl acetate 7/3) to be purified. This produced 1.8 g (30% of the theoretical value) subject 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 102169-44-8.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROEHN, ULRIKE; ELLERMANN, MANUEL; STRASSBURGER, JULIA; WENDT, ASTRID; ROEHRIG, SUSANNE; WEBSTER, ROBERTALAN; SCHMIDT, MARTINAVICTORIA; TERSTEEGEN, ADRIAN; BEYER, KRISTIN; SCHAEFER, MARTINA; BUCHMUELLER, ANJA; GERDES, CHRISTOPH; SPERZEL, MICHAEL; SANDMANN, STEFFEN; HEITMEIER, STEFAN; HILLISCH, ALEXANDER; ACKERSTAFF, JENS; TERJUNG, CARSTEN; (148 pag.)TW2016/5809; (2016); A;,
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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. 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H2Br2F2

1,3-dibromo-4, 6-difluorobenzene (50.0 g, 183. 9 mmol), 2-methoxyphenylboronic acid (67.1 g, 441. mmol), and a 2 M aqueous solution of Na2CO3 (368 mL, 736 mmol), DME (370 mL), toluene (370 mL), and Pd[PPh3]4 (21.3g, 18.4 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 8 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtrated and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 40.2 g in 67percent yield. FD-MS C20H16F2O2: theoretical value 326, observed value 326

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; Idemitsu Kosan Co., Ltd.; EP2301921; (2011); A1;,
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These common heterocyclic compound, 2051-99-2, name is 1-Bromo-4-isobutylbenzene, 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. SDS of cas: 2051-99-2

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4×10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.5 (S)-Benzyl 2-(4-isobutylphenyl)propanoate 7e Colorless oil, 93% yield, 91:9 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (8.0% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, minor tr = 16.94 min (R), major tr = 21.49 min (S)). [alpha]D20 = +76.1 (c 1.1, CHCl3). 1H NMR (300 MHz, CDCl3) delta: 7.36-7.07 (m, 9H), 5.15-5.06 (m, 2H), 3.75 (q, J = 7.2 Hz, 1H), 2.45 (d, J = 7.2 Hz, 2H), 1.89-1.80 (m, 1H), 1.51 (d, J = 7.2 Hz, 3H), 0.90 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta: 174.5, 140.5, 137.6, 136.1, 129.3, 128.4, 127.9, 127.7, 127.2, 66.2, 45.1, 45.0, 30.2, 22.3, 18.4. HRMS (APCI-TOF): calcd for C20H25O2 [M+H]+ 297.1855, found 297.1854.

The synthetic route of 1-Bromo-4-isobutylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
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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. 2576-47-8, name is 2-Bromoethylamine hydrobromide, A new synthetic method of this compound is introduced below., COA of Formula: C2H7Br2N

A cooled (0 C.) mixture of 2-bromoethylamine hydrobromide (12.000 g ; 58.56 mmol ; 1.0 eq.) in dioxane (60 ml) was treated with aq. 1M NaOH (117.2 ml ; 117.20 mmol ; 2.0 eq.), and dropwise (over 10 min.) with benzyl chloroformate (8.4 ml ; 58.8 mmol ; 1.0 eq.). The resulting mixture was further stirred at 0 C., under nitrogen, for 10 min., and then at rt for 13 h. Et2O (300 ml) was added, and the colorless organic layer was further washed with water (75 ml), dried over anh. MgSO4, filtered, and finally concentrated to dryness under reduced pressure to afford (2-bromo-ethyl)-carbamic acid benzyl ester as a colorless oil which was further dried under HV (15.020 g ; 99%). LC-MS: tR=0.95 min. ; [M+H]+: no ionisation.

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; Aissaoui, Hamed; Boss, Christoph; Koberstein, Ralf; Siegrist, Romain; Sifferlen, Thierry; US2011/105514; (2011); A1;,
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