Tag: M.W=200-300

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. 22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromobenzo[c][1,2,5]thiadiazole

After reacting lithium diisopropylamide (LDA) with N-Boc-3-methylindole in tetrahydrofuran (THF) at -20 ° C.,Triisopropyl borate was added and reacted for 1.5 hours to obtain N-Boc-3-methylindole-2-boronic acid.As shown by the following formula (8), “Boc” represents a tert-butoxycarbonyl group.Next, without isolating the obtained boronic acid, in the presence of tetrakis (triphenylphosphine) palladium (20 molpercent),The reaction was allowed to proceed at 95 ° C. for 4 hours in a mixed solvent of 4-bromo-2,1,3-benzothiadiazole and dioxane / potassium carbonate aqueous solution to obtain an indolylbenzothiadiazole derivative 1a in a yield of 84percent

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; YOKOHAMA NATIONAL UNIVERSITY; ITO, SUGURU; ASAMI, MASATOSHI; YAMADA, TAKESHI; TAGUCHI, TOMOHIRO; (23 pag.)JP2017/57191; (2017); A;,
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Electric Literature of 103273-01-4, These common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, 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 2-bromo-4-tert-butylaniline (2.28 g, 10 mmol), 2,5-dimethoxytetrahydrofuran (4.2 g, 30 mmol) and glacial acetic acid (150 mL) in a 250 mL three-necked RB flask was refluxed under nitrogen for 17 h. Then it was cooled, poured into aq. HCl (200 mL) and extracted with CH2Cl2, then combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was purified by column chromatography (PE) to afford 3ac as a white powder (1.97 g, 52 %); Rf = 0.28 (PE); m. p. 138 -140 C; 1H-NMR (CDCl3, 300 MHz) delta: 8.18 (d, J = 7.5 Hz, 2H), 7.85 (d, J = 11.4 Hz, 1H), 7.55 (d, J = 10.8 Hz, 1H), 7.42 (m, 3H), 7.29 (m, 2H), 7.12 (d, J = 7.8 Hz, 2H), 1.45 (s, 9H); 13C-NMR (CDCl3, 100 MHz) delta: 153.85, 141.01, 133.88, 131.20, 130.45, 126.03, 125.89, 123.42, 123.20, 120.35, 119.89, 110.18, 36.06, 31.32.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
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These common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-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. Recommanded Product: 5-Bromo-N1-methylbenzene-1,2-diamine

To a stirred solution of 5-bromo-N1-methylbenzene-1,2-diamine (38 g, 189 mmol) in THF (800 mL) was added CDI (37 g, 228 mmol) at room temperature under nitrogen atmosphere. The resulting mixture was refluxed for 16 h. The mixture was cooled to room temperature. The mixture was diluted with water (1 L) and stirred at room temperature for 30 min. The precipitated solids were collected by filtration and washed with water (200 mL). The filter cake was dried under vacuum to afford 6-bromo-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one (40 g, 93%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d 11.02 (br s, 1H), 7.35 (d, J = 1.9 Hz, 1H), 7.14 (dd, J = 8.2, 1.9 Hz, 1H), 6.92 (d, J = 8.2 Hz, 1H), 3.27 (s, 3H). LC/MS (ESI, m/z): [(M + 1)]+ = 227.10, 229.10

The synthetic route of 5-Bromo-N1-methylbenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); A1;,
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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. Computed Properties of C6H3BrN2S

5-bromobenzo[c][1,2,5]thiadiazole (5.00 g, 23.3 mmol), 2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (9.80 g, 34.9 mmol), potassium carbonate (8.03 g, 58.1 mmol), Dimethoxyethane (DME) (100 mL), and Water (25 mL) were combined in a flask. The solution was purged with nitrogen for 15 min then palladium tetrakis (1.34 g, 1.16 mmol) was added. The reaction was heated to reflux under nitrogen overnight. The reaction mixture was extracted with ethyl acetate (3 times), then washed with Brine and Water. The crude solid was purified with silica gel using 60/40 heptanes/Ethyl Acetate as the solvent system to afford a 4.70 g (70% yield) of a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1753-75-9, its application will become more common.

Reference:
Patent; Universal Display Corporation; BOUDREAULT, Pierre-Luc T.; ALLEYNE, Bert; XIA, Chuanjun; (154 pag.)US2018/13077; (2018); A1;,
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Synthetic Route of 1195-33-1, A common heterocyclic compound, 1195-33-1, name is 4-Bromobenzenesulfinic acid, molecular formula is C6H5BrO2S, 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: To a mixture of alkynyliodine 1 (0.1 mmol), sulfinic acid 2 (0.2 mmol) in DME (2 mL) at room temperature under air. The reaction vessel was sealed and allowed to stir for 12 h at 100 C. After completion of the reaction, the resulting mixture was concentrated under vacuum and the residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 3.

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:
Article; Wang, Leilei; Wei, Wei; Yang, Daoshan; Cui, Huanhuan; Yue, Huilan; Wang, Hua; Tetrahedron Letters; vol. 58; 51; (2017); p. 4799 – 4802;,
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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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-4-isobutylbenzene

A mixture of 5.0 g (23.5 mmol) of 1-bromo-4-isobutylbenzene, 3.14 g (26.7 mmol) of zinc cyanide, 963 mg (2.35 mmol) of dicyclohexyl-(2′,6′-dimethoxybiphenyl-2-yl)phosphane and 1.08 g (1.17 mmol) of tris(dibenzylidene-acetone)dipalladium in 230 ml of DMF/water (99:1) was heated at 120 C. under inert, oxygen-free conditions for 1 h. After cooling to RT, the mixture was diluted with approx. 1,000 ml of water and extracted three times with approx. 150 ml of ethyl acetate each time. The combined organic extracts were washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the filtrate was freed from the solvent on a rotary evaporator. The residue obtained was purified by means of filtration with suction over silica gel with cyclohexane/ethyl acetate 10:1 as the mobile phase. 3.04 g (81% of th.) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 7.56 (d, 2H), 7.23 (d, 2H), 2.53 (d, 2H), 1.94-1.83 (m, 1H), 0.90 (d, 6H).GC/MS (method K, EIpos): Rt=4.05 min, m/z=159 [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; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/301122; (2011); A1;,
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Application of 73918-56-6, These common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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: Procedure A: The reaction mixture of 7 (17 mg, 0.05 mmol), an appropriate amine (0.3 mmol), acetic acid (17.2 muL, 0.3 mmol), and sodium cyanoborohydride (0.16mmol) in MeOH (1 mL) was stirred in a sealed pressure tube at 50C for overnight. The reaction was then cooled to room temperature and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography.

The synthetic route of 73918-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Hao; Bruhn, David F.; Maddox, Marcus M.; Singh, Aman P.; Lee, Richard E.; Sun, Dianqing; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4070 – 4076;,
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Reference of 67567-26-4,Some common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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.

4-bromo-2,6-difluoroaniline (0.300g, 1.44mmol) was weighed into a vial, THF (3mL) was added. Intermediate H (407 mg, 1.44mmol) was added as a solid, followed by TEA (0.437g, 4.37 mmol). The vial was capped and the reaction was heated at 60 0C overnight. Product was precipitated by the addition of hexanes. The solids were rinsed with 2: 1 hexanes/ether to yield clean product (66%). 1H-NMR (DMSO-J6) delta 10.0 (s, IH), 9.27 (s,lH), 8.51 (d, J = 5.4 Hz, IH), 7.91 (s, IH), 7.55 (m, 2H) 7.37 (m, IH), MS [M+H]+ = 396.0, LCMS RT = 3.62 min.

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
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Reference of 626-40-4, 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. 626-40-4, name is 3,5-Dibromoaniline, This compound has unique chemical properties. The synthetic route is as follows.

It was diluted with dioxane and EtOAc, filtered through celite, concentrated and subjected to flash column with 0-5% MeOH in DCM to isolate 3-bromo-5-(2H-1,2,3-triazol-2-yl)aniline (273 mg), 3,5-di(2H-1,2,3-triazol-2-yflaniline (559 mg), 3-(1H-1,2,3-triazol-1-yl)-5-(2H-1,2,3-triazol-2-yl)aniline (636 mg), and 3,5-di(1H-1,2,3-triazol-1-yl)aniline (100 mg). The mixture of tert-tutyl ((1S,2R)-2-((6-chloro-5-cyanopyrazin-2-yl)amino)cyclohexyl)carbamate (90 mg, 0.26 mmol), 3,5-di(2H-1,2,3-triazol-2-yl)aniline (88 mg, 0.39 mmol), powder cesium carbonate (340 mg, 1.04 mmol), BINAP (31 mg, 0.05 mmol), Pd(OAc)2 (12 mg, 0.05 mmol) in 15 mL dioxane was degassed with argon stream. It was stirred in argon atmosphere at 110 C. for 16 h. The mixture was cooled, diluted with 100 mL EtOAc, vigorously stirred, and filtered through celite. The filtrate was concentrated and subjected to silica flash column with 0-55% EtOAc in hexane to isolate the coupling product. It was then stirred in 5 mL TFA and 1 mL conc. H2SO4 at 80 C. for 20 m.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
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Application of 51554-93-9, 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 51554-93-9 as follows.

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.

According to the analysis of related databases, 51554-93-9, the application of this compound in the production field has become more and more popular.

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;,
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