Tag: M.W=200-300

Application of 69321-60-4, 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 69321-60-4 as follows.

A 100-mL three-neck round-bottomed flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet was charged with 102b (1.00 g, 5.37 mmol), (2.69 g, 10.7 mmol), cesium carbonate (3.49 g, 10.7 mmol), N,N’-dimethylethylenediamine (473 mg, 5.37 mmol) and 1 ,4-dioxane (45 mL). After bubbling nitrogen through the resulting suspension for 30 min, copper iodide (510 mg, 2.69 mmol) was added, and the reaction mixture was heated at 105 C (oil bath temperature) for 14 h. After this time, the mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (200 mL) and water (40 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 62% yield (1.18 g) of 102c as an off-white solid: mp 178-180 C; ]H NMR (300 MHz, CDC13) delta 7.74 (dt, 1H, / = 8.2, 1.0 Hz), 7.58 (dd, 1H, / = 7.8, 1.2 Hz), 7.37 (m, 3H), 7.19 (m, 3H), 4.45 (m, 2H), 4.21 (m, 1H), 3.95 (m, 1H), 2.38 (s, 3H); MS (ESI+) m/z 355.0 (M+H).

According to the analysis of related databases, 69321-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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 73918-56-6, Quality Control of 2-(4-Bromophenyl)ethanamine

(1835) [00528] Into an 8 mL reaction vial was added methyl 3-amino-6-cyclopropylthieno[2,3- ¡ê]pyridine-2-carboxylate (0.100 g, 0,403 mmol) and 2-(4-bromophenyl)ethanamine (0,121 g, 0,604 mmol) followed by a mixture of toluene/THF (10: 1; 2.2 mL), A solution of trimethy 3 aluminum (2 M in toluene, 0,604 mL, 1.21 mmol) was added and the reaction mixture was heated to 80 C overnight. The reaction was quenched with a saturated solution of NaHCO, (2 mL), heated at 50 C for 30 minutes, and then extracted with ethyl acetate (2 x 3 mL). The combined organic layers were washed with brine (3 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide a crude product that was suspended in ethyl acetate (2 mL) and sonicated for 15 minutes. The resulting white precipitate was filtered, washed with ethyl acetate (3 mL), and dried in vacuo overnight to afford 3-amino-Ar-(4-bromophenethyl)-6- cyclopropyithieno[2,3-/ ]pyridine-2-carboxamide (139 mg, 83 % yield), LCMS (ESI, m/z): 416

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; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 118527-30-3, 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. 118527-30-3, name is 2-Bromo-1,3-bis(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 50 mL round bottomed flask fitted with a rubber septum was charged with a stir bar, Pd(OAc)2 (74.8 mg, 0.33 mmol, 3 mol %, Johnson Matthey), SPhos (275.1 mg, 0.67 mmol, 6 mol %, Strem), 2-bromo-1,3-bis(trifluoromethyl)benzene (3.25 g, 11.1 mmol, 1.0 equiv, Synquest Laboratories) and K3PO4 (4.71 g, 22.2 mmol, 2.0 equiv, Strem). The flask was evacuated and backfilled with N2 (¡Á3). Toluene (20 mL) and degassed DI H2O (2 mL) were added followed by 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (5.82 g, 16.6 mmol, 1.5 equiv). The rubber septum was quickly replaced with a yellow polyethylene cap and secured with electrical tape. The reaction was heated at 100 C. in an oil bath for 16 h, at which time it was allowed to cool to room temperature and quenched with water (10 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3¡Á10 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica (300 mL) eluting with 5% EtOAc/hexanes afforded the title compound in approximately 61% yield with some minor impurities resulting from protodeboronation of the pinacol borane. The product was taken on to subsequent synthetic steps during the course of which, the impurities were removed.

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, 2-Bromo-1,3-bis(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Board of Trustees of the University of Illinois; White, M. Christina; Gormisky, Paul E.; (58 pag.)US9925528; (2018); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

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.

99.7 g (0.437 mol) of Intermediate 41 and 997 ml of tetrahydrofuran were added. 100.2 g (0.454 mol) of Intermediate 122 was dissolved in 506 ml of tetrahydrofuran and then, was slowly added thereto, followed by stirring for about 2 hours. After finishing the reaction, solvents were removed by distillation under a reduced pressure. The resultant product was extracted using EA and a sodium carbonate aqueous solution, and water was removed with MgSO4. Solvents were removed by distillation under a reduced pressure, and the resultant product was solidified to obtain 155.6 g (86.4%) of ivory Intermediate 123.

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

Reference:
Patent; SAMSUNG DISPLAY CO., LTD.; LAPTO CO., LTD.; BAE, Sung-soo; CHO, Hwanhee; OH, Eu-gene; JEONG, Hyein; KIM, Gyuri; HAN, Kap-jong; KIM, Namho; KIM, Hyejeong; MAENG, Juwan; PARK, Yongpil; YOON, Jeunghun; (531 pag.)US2019/181358; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 445303-69-5,Some common heterocyclic compound, 445303-69-5, name is 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, molecular formula is C7H4BrF3, 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 10 mL microwave vial was added 4-(4-fluorophenyl)-l-(l-methyl-lH-imidazol-4- ylsulfonyl)pyrrolidin-3 -amine hydrochloride (100 mg, 0.277 mmol) and premixed tris(dibenzylidene- acetone)dipalladium(0)/sodium tert-butoxide/ 2,2′-bis(diphenylphosphino)-l ,1 ‘-binaphthyl (100 mg, 0.05:0.15:2), aldrich 715530). The solids were suspended in 1 ,2-dimethoxyethane, and 4-bromo-2- (difluoromethyl)-l -fluorobenzene (74.8 mg, 0.333 mmol) was added. The reaction vessel was capped and the reaction mixture was heated in a microwave (Biotage Initiator, maximum 400 Watts) for 15 min at 130C. The mixture was filtered through celite, concentrated, dissolved in 2 ml 50% methanol/dimethylsulfoxide, and purified by HPLC to provide the title compound. MS (ESI) m/z 469 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, its application will become more common.

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; ABBVIE INC.; AMBERG, Wilhelm; POHLKI, Frauke; LANGE, Udo; WANG, Ying X.; ZHAO, Hongyu H.; LI, Huan-Qiu; BREWER, Jason T.; ZANZE, Irini; DIETRICH, Justin; VASUDEVAN, Anil; DJURIC, Stevan, W.; LAO, Yanbin; HUTCHINS, Charles W.; WO2014/140310; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 91319-54-9, 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. 91319-54-9, name is 1-(2-Bromoethyl)-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 134 Synthesis of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline 1-(Piperidin-4-yl)-6-acetamidomethylindoline (250 mg) and 2-fluorophenethyl bromide (220 mg) were treated as in Example 2 to give the title compound (190 mg) as a white-powder (yield: 52%). m.p.: 160-161 C. 1H-NMR (400 MHz, CDCl3): delta(ppm) 1.51-1.68(2H, m), 1.81-1.92(2H, m), 2.00(3H, s), 2.20-2.40(2H, m), 2.70-2.89(4H, m), 2.91(2H, t, J=8Hz), 3.01-3.10(2H, m), 3.40-3.48(3H, m), 4.32(2H, d, J=6Hz), 6.39(1H, s), 6.51(1H, d, J=8Hz), 6.98-7.10(3H, m), 7.18-7.30(2H, m). FAB-Mass: 396(MH+).

The synthetic route of 1-(2-Bromoethyl)-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); 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. 53398-55-3, name is 1-Bromo-3,5,7-trimethyladamantane, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H21Br

Example 6: l-Acetamido-3.5.7-dirnethyladamantane (Ac-NH-TMAD) synthesis; 4 g of l-bromo-3,5,7-trimethyladamantane, 12 g (15 ml) of acetonitrile, and 7 g of 75% phosphoric acid are added to a 50ml reactor equipped with condenser, mechanical stirrer, thermometer at 20-250C and under nitrogen. After addition, the internal temperature rises to 30-320C. The obtained biphasic system is warmed to 87+/-2C over about 30 min (slight reflux) and the temperature maintained for 17 hrs. During the course of the reaction, a monophasic system is obtained. At this point, the reaction is complete. n-butanol (15ml), toluene (15ml) and water (15ml) are added and the resulting biphasic system is cooled to 20-250C. Sodium hydroxide 30% is added to reach pH 6-7 and the temperature rises to 40-450C. Phases are separated at 35-400C and the aqueousphase is discarded. Water (15ml) is loaded to the organic phase and, after stirring and standing, the phases are separated at 40-45. The organic phase is concentrated under vacuum (res. pressure 45-50 mmHg, external temperature 80-850C, internal temperature 40-700C) until a residual volume of 6-6.5ml is obtained. After cooling to 55-600C, acetone (30ml) is added. The resulting suspension is warmed to reflux (62-63C) until complete dissolution is obtained. After cooling to 500C, water (50ml) is slowly added and crystallization of l-acetamido-3,5,7-dimethyladamantane occurs. After 1.5-2hrs at 18+/-3C, the solid is filtered, washed with water and dried at 45-500C for 15hrs. Dry weight: 3.3g 1H NMR is reported: 1H-NMR in CDCl3 (298K)

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; TEVA PHARMACEUTICAL FINE CHEMICALS S.R.L.; TEVA PHARMACEUTICALS USA, INC.; WO2007/126886; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 89359-54-6, These common heterocyclic compound, 89359-54-6, name is 9-Bromo-1-nonene, 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 flame dried 500 mL RB flask, freshly activated Mg turnings (9 g) were added and the flask was equipped with a magnetic stir bar, an addition funnel and a reflux condenser. This set-up was degassed and flushed with argon and 100 mL of anhydrous ether was added to the flask via syringe. The bromide 3 (51.3 g, 250 mmol) was dissolved in anhydrous ether (100 mL) and added to the addition funnel. About 5 mL of this ether solution was added to the Mg turnings while stirring vigorously. An exothermic reaction was noticed (to confirm/accelerate the Grignard reagent formation, 5 mg of iodine was added and immediate decolorization was observed confirming the formation of the Grignard reagent) and the ether started refluxing. The rest of the solution of the bromide was added dropwise while keeping the reaction under gentle reflux by cooling the flask in water. After the completion of the addition the reaction mixture was kept at 35 C for 1 hour and then cooled in ice bath. Ethyl formate (9 g, 121 mmol) was dissolved in anhydrous ether (100 mL) and transferred to the addition funnel and added dropwiseto the reaction mixture with stirring. An exothermic reaction was observed and the reaction mixture started refluxing. After the initiation of the reaction the rest of the ethereal solution of formate was quickly added as a stream and the reaction mixture was stirred for a further period of 1 h at ambient temperature. The reaction was quenched by adding 10 mL of acetone dropwise followed by ice cold water (60 mL). The reaction mixture was treated with aq. H2S04 (10 % by volume, 300 mL) until the solution became homogeneous and the layers were separated. The aq. phase was extracted with ether (2×200 mL). The combined ether layers were dried (Na2S04) and concentrated to afford the crude product which was purified by column (silica gel, 0-10% ether in hexanes) chromatography. The product fractions were evaporated to provide the pure product 249 as a white solid (30.6 g, 90%). 1H NMR (400 MHz, CDC13) delta 7.26 (s, 1H), 5.81 (ddt, J = 16.9, 10.2, 6.7 Hz, 8H), 5.04 – 4.88 (m, 16H), 3.57 (dd, J = 7.6, 3.3 Hz, 4H), 2.04 (q, J = 6.9 Hz, 16H), 1.59 (s, 1H), 1.45 (d, J = 7.5 Hz, 8H), 1.43 – 1.12 (m, 94H), 0.88 (t, J = 6.8 Hz, 2H). 13C NMR (101 MHz, cdcl3) delta 139.40, 114.33, 77.54, 77.22, 76.90, 72.21, 37.70, 34.00, 29.86, 29.67, 29.29, 29.12, 25.85.

The synthetic route of 89359-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALNYLAM PHARMACEUTICALS, INC.; MAIER, Martin; JAYARAMAN, Muthusamy; AKINC, Akin; MATSUDA, Shigeo; KADASAMY, Pachamuthu; RAJEEV, Kallanthottathil, G.; MANOHARAN, Muthiah; WO2013/86354; (2013); A1;,
Bromide – Wikipedia,
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Related Products of 445-02-3, 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. 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

Step A: N-(4-Bromo-2-trifluoromethyl-phenyl)-3,3-dimethylbutanamide 3,3-Dimethylbutanoyl chloride (617 mg, 0.64 mL, 4.6 mmol) was added to a solution of 4-Bromo-2-trifluoromethyl-phenylamine (1.0 g, 4.16 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature overnight. Water was added to the mixture and the precipitate formed collected to give the title compound as a powder (1.1 g, 79% yield).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-(trifluoromethyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Valeant Pharmaceuticals North America; US2008/139610; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

73918-56-6, name is 2-(4-Bromophenyl)ethanamine, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 2-(4-Bromophenyl)ethanamine

Intermediate 991 ,1 -Dimethylethyl [2-(4-bromophenyl)ethyl]carbamate Bis(1 ,1 -dimethylethyl) dicarbonate (240 mg, 1.100 mmol) was added to a mixture of [2-(4- bromophenyl)ethyl]amine 2-(4-bromophenyl)ethanamine (200 mg, 1 .000 mmol) and DIPEA (0.524 mL, 3.00 mmol) in dichloromethane (DCM) (5 mL). The resulting mixture was stirred under nitrogen at room temperature for 2 h then concentrated in vacuo. The residue was partitioned between AcOEt (20 mL) and water (15 mL) and the layers were separated. The aqueous phase was extracted with AcOEt (15 mL). The combined organic phases were washed with brine (15 mL), dried over MgS04 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 5 to 25% AcOEt in hexanes) gave 1 ,1 -dimethylethyl [2-(4-bromophenyl)ethyl]carbamate (256mg, 0.853mmol, 85%) as a white solid.LCMS (method G): Retention time 1.22 min, [M+H-t-Bu]+ = 244.0 (1 Br)

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

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary