Category: bromides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 114078-88-5, name is 5-Bromo-1,2,3-triazine, 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 114078-88-5, Computed Properties of C3H2BrN3

To a solution of compound S3 (400 mg, 2.5 mmol) in CHCl3(10 mL) was added 1-(cyclopent-1-en-1-yl)pyrrolidine (516 mg, 3.8 mmol). The reaction was stirred at 45 C. for 16 hrs. The reaction mixture was diluted with DCM and washed water, brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel column (eluted with EtOAc/PE=1/10) to give the title compound (170 mg, 34.3% yield) as a gray solid.

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; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
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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;,
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. 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;,
Bromide – Wikipedia,
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Reference of 3814-30-0, 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. 3814-30-0, name is (Bromomethyl)cyclopentane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1-9-1 Preparation of N-(cyclopentylmethyl)-2-[1 -(cyclopentylmethyl)-1 H-indazol-3-yl]-5- methoxypyrimidin-4-amine 610 mg 2-(1 H-indazol-3-yl)-5-methoxypyrimidin-4-amine (2.5 mmol, 1 .0 eq.) was dissolved in 4 mL DMF and treated with 1 1 1 mg sodium hydride (60 %, 2.9 mmol, 1 .1 eq.) at room temperature under Argon atmosphere. It was stirred for 15 minutes, then the 93 mg Tetra-n-butylammoniumiodid (0.25 mmol, 0.1 eq.) was added and the mixture was cooled down to 0. 453 mg (bromomethyl )cyclopentane (2.9 mmol, 1 .1 eq), dissolved in 1 mL DMF, was added dropwise. It was stirred in the ice bath for 10 minutes and at room temperature for 2 days. The reaction mixture was diluted with dichloromethane and water, extracted three times with dichloromethane. The collected organic layers washed once with water and brine, filtered through a silicone coated filter and concentrated in vacuo. The crude product was treated with hexane and stirred. The unsolved residue was filtered off. The residue was treated with Methanol and stirred. The unsolved residue was filtered off: 375 mg, 99% pure, 1 .2 mmol, 45%. 1 H-NMR (400 MHz, DMSO-d6) delta [ppm] = 1 .26 – 1 .40 (m, 2H), 1 .44 – 1.72 (m, 6H), 2.53 – 2.58 (m, 1 H), 3.90 (s, 3H), 4.37 (d, 2H), 6.87 (br. s, 2H), 7.16 – 7.24 (m, 1 H), 7.35 – 7.44 (m, 1 H), 7.70 (d, 1 H), 8.00 (s, 1 H), 8.58 (d, 1 H).

The synthetic route of (Bromomethyl)cyclopentane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HITCHCOCK, Marion; MENGEL, Anne; MUeLLER, Thomas; BAeRFACKER, Lars; CLEVE, Arwed; BRIEM, Hans; SIEMEISTER, Gerhard; BONE, Wilhelm; FERNANDEZ-MONTALVAN, Amaury, Ernesto; SCHROeDER, Jens; MOeNNING, Ursula; HOLTON, Simon; PREUSSE, Cornelia; (165 pag.)WO2017/157991; (2017); A1;,
Bromide – Wikipedia,
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Synthetic Route of 39478-78-9, 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. 39478-78-9 name is 5-Bromo-2-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.

General procedure: To a solution of 3-bromo-5-methoxyaniline (11b) (150.0 mg, 0.74 mmol) and a catalyticamount of DMAP in anhydrous CH2Cl2 (8 mL) was added pyridine(0.08 mL, 0.55 mmol) and 2-propanesulfonyl chloride (0.09 mL,0.82 mmol) under an argon atmosphere. The mixturewas stirred atroom temperature for 40 h. After being quenched with 1 N HCl(aq)(0.5 mL) and water, CH2Cl2 were added, and the layers wereseparated. The combined organic phases were washed with brine,dried over anhydrous Na2SO4, filtered and concentrated. The residuewas purified by column chromatography on silica gel (EtOAc/hexane,10:90 to 20:80) to give 13e (67.8 mg, 30%) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-methylaniline, and friends who are interested can also refer to it.

Reference:
Article; Bufton, Joshua C.; Bullock, Alex N.; Cuny, Gregory D.; Dai, Bing; Degterev, Alexei; Duddupudi, Anantha Lakshmi; Gyrd-Hansen, Mads; Hu, Ming; Li, Li; Pinkas, Daniel M.; Schlicher, Lisa; Suebsuwong, Chalada; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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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;,
Bromide – Wikipedia,
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Reference of 7745-91-7, 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. 7745-91-7, name is 3-Bromo-4-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 3-(trifluoromethyl) benzoic acid (511mg, 2.69mmol) was stirred in a solvent of 58 dimethyl formamide (10mL).The reaction solution was added with 59 HATU (1.12g, 2.96mmol), 72 DIPEA (890mul, 5.37mmol) and the appropriate substituted aromatic amine (500mg, 2.69mmol), followed by stirring for about 8h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting mixture was concentrated to give the crude product, which was purified by silica gel column chromatography (eluting with 0-5% EtOAc in 82 petroleum ether) to afford the 110 product as a white solid (815mg, 84%). 1H NMR (400MHz, Methanol-d4) delta 8.27 (s, 1H), 8.21 (d, J=8.4Hz, 1H), 8.06 (d, J=1.8Hz, 1H), 7.91 (d, J=7.4Hz, 1H), 7.75 (t, J=8.0Hz, 1H), 7.59 (dd, J=8.3, 1.8Hz, 1H), 7.30 (d, J=8.4Hz, 1H), 2.40 (s, 3H). MS m/z: 358.12 ([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, 3-Bromo-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Qi; Dai, Yang; Ji, Yinchun; Shi, Huanyu; Guo, Zuhao; Chen, Danqi; Chen, Yuelei; Peng, Xia; Gao, Yinglei; Wang, Xin; Chen, Lin; Jiang, Yuchen; Geng, Meiyu; Shen, Jingkang; Ai, Jing; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 671 – 689;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7051-34-5,Some common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, molecular formula is C4H7Br, 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 methyl 3-hydroxy-4-methoxybenzoate (5 g, 27.47 mmol) in DMF (30 mL) were added anhydrous potassium carbonate (7.58 g, 54.95 mmol) and (bromomethyl) cyclopropane (3.8 mL, 41.20 mmol) in turn. The mixture was stirrred in a sealing tube at 60 for 4.5 h. The reaction mixture was diluted with saturated aqueous NaCl solution (20 mL) . The resulting mixture was extracted with EtOAc (25 mL × 3) . The combined organic layers were washed with water (30 mL × 3) , dried over anhydrous Na2SO4 for 1 h and concentrated to give the title compound as a white solid (6.26 g, 96.5) 1H NMR (400 MHz, CDCl3) : delta ppm 7.66 (d, J 8.4 Hz, 1H) , 7.52 (s, 1H) , 6.87 (d, J 8.4 Hz, 1H) , 3.92 (s, 3H) , 3.89 (d, J 7.0 Hz, 2H) , 3.87 (s, 3H) , 1.32-1.36 (m, 1H) , 0.62-0.67 (m, 2H) , 0.34-0.38 (m, 2H) and MS-ESI: m/z 237.1 [M+H] +.

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LIU, Bing; YU, Tianzhu; ZHANG, Xiangyu; ZHANG, Shiguo; ZHANG, Jiancun; CHENG, Changchung; (426 pag.)WO2016/34134; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary