Tag: M.W=100-200

55289-36-6, name is 3-Bromo-2-methylaniline, 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. 55289-36-6

To a solution of 10.0 g (53.7 mmol, 1.0 eq.) of 3-bromo-2-methylamine (LXXXVIIa) in 200 mL of acetonitrile at 0 C was added 42 mL of cone. HC1 followed by 42 mL of glacial acetic acid and a solution of 4.4 g (63.9 mmol, 1.1 eq.) of sodium nitrite in 12 mL of water. The mixture was purged with SO2 gas for 15 mm and a solution of 9.1 g (53.7 mmol, 1.0 eq.) ofcopper (II) chloride in 12 mL of water was added dropwise at 0 C. The mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was concentrated in vacuo, diluted with 500 mL of water and extracted with 3 x 500 mL of ethyl acetate. The combined organic extracts were washed with 200 mL of sat. aqueous sodium bicarbonate solution, 200 mL of brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue waspurified by trituration with pentane to provide 8.0 g (29.7 mmol, 55%) of 3-bromo-2- methylbenzene-1-sulfonyl chloride (LXXXVIIIa). ?H NIVIR (400 MFIz, CDC13): 8.07 (d, 1H), 7.92 (d, 1H), 7.28 (t, 1H), 2.88 (s, 3H).

Statistics shows that 55289-36-6 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-methylaniline.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
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These common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, 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. 1647-23-0

The first step, weighed indole acetic acid (1.05g),Added to DMF (5 mL) and stirred to dissolve,Cooling to 0 ~ 5 C stirring;60% sodium hydride (0.72 g) was added,Stirring for 10min,3,3-dimethyl-1-bromobutane(1.5 g) was added,0 ~ 5 C reaction 0.5h,Slowly rose to room temperature reaction 2h;Add ethyl acetate (40mL), water (40mL); rapid mixing, 2min drop 6N hydrochloric acid solution 10mL,Stirring for 5 min; the phases were separated and the aqueous phase was extracted with ethyl acetate (20 mL). The phases were separated and the ethyl acetate phases were combined. Saturated brine(30 mL) for 5 min,The ethyl acetate phase was removed at 50 C under reduced pressure to give the crude product of the first step2- [1- (2-tert-butylethyl) -1H-indol-3-yl] acetic acid.

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 1647-23-0.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Shi Jiangong; Guo Ying; Xu Chengbo; Chen Qing; Chen Minghua; Ba Mingyu; Zhu Chenggen; Tang Ke; Jiang Jiandong; Guo Jiamei; Guo Qinglan; Lin Sheng; Yang Yongchun; (44 pag.)CN107151223; (2017); A;,
Bromide – Wikipedia,
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39478-78-9, name is 5-Bromo-2-methylaniline, 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. 39478-78-9

General procedure: An equimolar mixture of isatin/5-bromoisatin and an aromatic primary amine were introduced into an Erlenmeyer flask. Ethanol (1 mL) and a few drops of acetic acid were added. The Erlenmeyer flask was placed in an ultrasonic bath filled with water (80 Hz,100%), the temperature was adjusted at 40C. At the end of the reaction (monitored by TLC), the product obtained by filtration was recrystallized from ethanol. For the reactions carried out in microwave Biotage, the reagents in 4 mL of ethanol were put in a magnetic stir bar for 2-5 mL vial and the temperature was set at 150C, 160C then 180C.

Statistics shows that 39478-78-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methylaniline.

Reference:
Article; Chemchem, Meryem; Menacer, Rafik; Merabet, Naima; Bouridane, Hamida; Yahiaoui, Samir; Moussaoui, Sadjia; Belkhiri, Lotfi; Journal of Molecular Structure; vol. 1208; (2020);,
Bromide – Wikipedia,
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Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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. 55289-36-6

To a solution of compound 298a (8g, 43mmol) in dichloromethane (80ml) at 0 C was added compound 298b (16ml, 113.5mmol). The reaction solution was stirred at 0 C for 30 minutes, and then solid potassium nitrate (5.43g, 53.7 mmol), the ice bath was removed, and the reaction solution was stirred at room temperature for 4 hours. LCMS monitored the reaction of the raw materials. The reaction solution was concentrated and dried under vacuum. The residue was added with water and extracted twice with dichloromethane (2 * 200 ml). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered with suction.It was dried and the crude product was passed through the column to obtain a yellow solid compound (Example 298c, 4.0972g, yield 28.57%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 55289-36-6, its application will become more common.

Reference:
Patent; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
Bromide – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 461-96-1, name is 1-Bromo-3,5-difluorobenzene, 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 461-96-1. 461-96-1

Under a nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (7.3 g) was dissolved in THF (30 mL) and cooled to -70 C. or lower.To the solution, a 1.6 M butyl lithium / hexane solution (32 mL) was added dropwise at a rate such that the internal temperature did not reach -65 C. and then stirred at -70 C. or lower for 30 min.Subsequently, a solution prepared by dissolving 3,5-difluorobromobenzene (10 g) in THF (50 mL) was added dropwise to the stirring reaction solution at a rate such that the internal temperature did not exceed -65 C., At room temperature for 1 hour to prepare phenyllithiums.In a separate reaction vessel, difluorodibromomethane (16.3 g) was dissolved in THF (160 mL)The dissolved solution was cooled to -70 C. or lower, and a solution of phenyllithium prepared in advance was added to the solution using a cannula, followed by stirring at -70 C. or lower for 1 hour, then cooled to room temperature .Water and hexane were added to the reaction solution to separate the organic layer, and the organic layer was washed twice with saturated brine.Sodium sulfate was added to the organic layer after washing and dried, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-bromo-2,6-difluoro- (bromodifluoromethyl) benzene and 1,4 – dibromo-2,6-difluorobenzene (13.7 g).When the ratio of each compound in the mixture was measured by gas chromatography,81.6% of 4-bromo-2,6-difluoro- (bromodifluoromethyl) benzene and 18.4% of 1,4-dibromo-2,6-difluorobenzene.

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 1-Bromo-3,5-difluorobenzene.

Reference:
Patent; DIC Corporation; Tojo, Kenta; Kusumoto, Tetsuo; Takatsu, Haruyoshi; (11 pag.)JP6047884; (2016); B2;,
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553-94-6,Some common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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: In a typical run, in the air atmosphere, a reaction tube was charged with aryl halide (1.0 mmol), phenylboronic acid (1.0 mmol), ionic Pd-NHC complex (0.001 mmol), and K2 CO3 (1 mmol). Solvent (2-propanol/H2 O, 1:2 v/v) (3 mL) was added to tube and the mixture was vigorously stirred at room temperature for a specific time. After the desired reaction time, 5 mL of diethyl ether was added to the reaction mixture, and the organic phase was extracted with the appropriate volume of water and dried over MgSO4 . Next, the organic phase (1 L ) was injected to GC. The reactions were monitored with a Shimadzu GC-2010 Plus (FID) (Kyoto, Japan). The results were the average of the 2 runs. The yields were determined by GC with use of undecane as the internal standard. All of the coupling products were previously reported. The turn over frequency (TOF) was calculated using the following equations: TOF = TON/time of reaction and TON = moles of desired product formed/moles of the catalyst.

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

Reference:
Article; Ya?ar, Sedat; Akkoc, Mitat; Oezdemir, Nam?k; Oezdemir, ?smail; Turkish Journal of Chemistry; vol. 43; 6; (2019); p. 1622 – 1633;,
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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 55289-36-6 as follows. 55289-36-6

General procedure: To a cooled solution of the chosen 2-methylaniline dissolved in HBF4 (50% solution in water; 15-30 mL) was added at 0 C dropwise a cooled aqueous solution of NaNO2 (1 equiv in the minimum of water). After the end of the addition, the mixture was stirred 1 h at 0 C and 2 h at room temperature. Then, the resulting precipitate was filtered, washed with Et2O (3 ¡Á 100 mL) and dried to obtain the corresponding 2-methylphenyldiazonium tetrafluoroborate salts which were directly added in one portion under nitrogen to a stirred mixture of KOAc (2 equiv) and 18-crown-6 (0.05 equiv) in dry CHCl3 (350-700 mL). After 2 h at room temperature, the mixture was filtered, washed with CHCl3 (3 ¡Á 100 mL) and the organic filtrate was finally concentrated in vacuo. The residual gum was purified by column chromatography on silica gel (EtOAc/cyclohexane 1:3) to give the desired indazoles 1 and 2a.

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lohou, Elodie; Sopkova-De Oliveira Santos, Jana; Schumann-Bard, Pascale; Boulouard, Michel; Stiebing, Silvia; Rault, Sylvain; Collot, Valerie; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5296 – 5304;,
Bromide – Wikipedia,
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3814-30-0, Name is (Bromomethyl)cyclopentane, 3814-30-0, 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.

Weigh 165.7mg (1.02mmol) of bromomethylcyclopentane and dissolve it in DMF, add it dropwise to the reaction flask and stir for 5min, and dropwise add 73mg (1.12mmol) of sodium azide solution ( DMF solution), argon protection, 100 C reflux stirring reaction for 12h, complete reaction was detected by TLC, add pure water, extract with EtOA, wash with water, dry with MgSO4, filter with suction and concentrate the dried product, then dissolve its EtOAc and add dropwise to the reaction flask During stirring for 5 min, 110 mg (1.02 mmol) of p-benzoquinone (EtOAc dissolved) was added dropwise, protected by argon, and the reaction was stirred at 70 C under reflux for 24 h. The reaction was completed by TLC, the reaction was terminated, and the crude product was obtained by concentration and drying. The crude product was separated by Combiflash (RediSep Column: Silica 20g, column retention volume was 78ml), and the elution gradient was EtOAc: PE = 20:80. The fractions were analyzed by TLC, combined and dried to obtain 22.5mg of compound ZY011901 and 22.5mg of compound ZY011903

Statistics shows that (Bromomethyl)cyclopentane is playing an increasingly important role. we look forward to future research findings about 3814-30-0.

Reference:
Patent; Guangzhou University Of Traditional Chinese Medicine (Guangzhou Traditional Chinese Medicine Institute); Liu Jiawei; Yu Qiang; Zheng Yangqing; Zhang Qing; Ma Hongyan; Zeng Xinling; Zhou Qing; Wen Liangxi; Liu Jingli; Li Min; Xia Fan; (49 pag.)CN110872299; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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 111721-75-6, 111721-75-6

To a solution of 2-bromo-3-fluoroaniline (2.0 g, 11 mmol) in CH2Cl2 (50 mL) was added butyryl chloride (1.3 g, 13 mmol) and pyridine (1.7 g, 21 mmol) at 0 C. The mixture was stirred at room temperature for 24 h. Water (20 mL) was added and the mixture was extracted with CH2Cl2 (50 mL¡Á3). The organic layers were dried anhydrous over Na2SO4 and evaporated under vacuum to give N-(2-bromo-3-fluorophenyl)butyramide (2.0 g, 73%), which was directly used in the next step.

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-3-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hadida Ruah, Sara S.; Grootenhuis, Peter D.J.; Van Goor, Frederick; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel; US2007/244159; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 5433-01-2, name is 1-Bromo-3-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. 5433-01-2

General procedure: The boronic acid pinacol ester (1 equiv.), aryl halide (1 equiv.) and Pd(dppf)Cl2¡¤CH2Cl2 adduct (0.1 equiv.) were dissolved in a mixture of DME and aqueous sodium carbonate (1M) in a microwave vial. The vial was sealed, evacuated and backfilled with N2. The reaction mixture was heated in the microwave at 120C for 45min and monitored by LCMS. The reaction mixture was concentrated in vacuo to give the crude material which was purified by Biotage column chromatography (see individual compounds for details of the eluent used).

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 5433-01-2.

Reference:
Article; Le Bihan, Yann-Vai; Lanigan, Rachel M.; Atrash, Butrus; McLaughlin, Mark G.; Velupillai, Srikannathasan; Malcolm, Andrew G.; England, Katherine S.; Ruda, Gian Filippo; Mok, N. Yi; Tumber, Anthony; Tomlin, Kathy; Saville, Harry; Shehu, Erald; McAndrew, Craig; Carmichael, LeAnne; Bennett, James M.; Jeganathan, Fiona; Eve, Paul; Donovan, Adam; Hayes, Angela; Wood, Francesca; Raynaud, Florence I.; Fedorov, Oleg; Brennan, Paul E.; Burke, Rosemary; van Montfort, Rob L.M.; Rossanese, Olivia W.; Blagg, Julian; Bavetsias, Vassilios; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 316 – 337;,
Bromide – Wikipedia,
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