Tag: M.W=200-300

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. Product Details of 103273-01-4

Example 7; N-{4-[7-tert-Butyl-5-(6-methoxy-2-oxo-1,2-dihydro-pyridin-3-yl)-quinoxalin-2-yl]-3-chloro-phenyl}-methanesulfonamide (I-12); step 1-; A microwave vial was charged with 58 (587 mg, 2.57 mmol), 5-fluoro-2-methoxy-pyridin-3-ylboronic acid (59, 660 mg, 3.86 mmol), Pd(PPh3)4 (148 mg, 0.12 mmol), Na2CO3 (818 mg, 7.8 mmol) and MeOH (0.7 mL)/DCM (3.5 mL), sealed and irradiated in a microwave synthesizer at 115 C. for 2 h. The reaction mixture was cooled to RT and diluted with EtOAc. The organic layer was washed with water, dried (MgSO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient to afford 460 mg (65%) of 60 as a brown oil.

The synthetic route of 2-Bromo-4-(tert-butyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; de Vicente Fidalgo, Javier; Li, Jim; Schoenfeld, Ryan Craig; Talamas, Francisco Xavier; Taygerly, Joshua Paul Gergely; US2010/311760; (2010); A1;,
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Related Products of 61613-22-7, These common heterocyclic compound, 61613-22-7, name is 2-Bromo-N-phenylaniline, 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.

10 g (42 mmol) of 2-bromo-N-phenylaniline and 150 ml of tetrahydrofuran were added to a reaction container, and the mixture was cooled to -78 C. using dry ice, After 3.323 g (52 mmol) of n-butyllithium was slowly dropwise added thereto, the resulting solution was stirred for 1 hour. 9.4 g (52 mmol) of 9H-fluorene-9-one was dissolved in 50 ml of tetrahydrofuran, and slowly dropwise added to the reaction container. After the reaction was completed, the solvent was evaporated and the resulting residue was thoroughly dried. 100 ml of acetic acid:hydrochloric acid (1:10 v/v) was added thereto, thereby obtaining 11.9 g (89%) of Intermediate I-16-1,

The synthetic route of 61613-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.; JEON, Soonok; KIM, Sangmo; KIM, Hyungjun; CHUNG, Yeonsook; JUNG, Yongsik; CHAE, Miyoung; HUH, Dalho; KIM, Joonghyuk; IHN, Sooghang; (87 pag.)US2017/5275; (2017); A1;,
Bromide – Wikipedia,
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Electric Literature of 90868-92-1,Some common heterocyclic compound, 90868-92-1, name is (4-Bromophenyl)(cyclopropyl)methanamine, molecular formula is C10H12BrN, 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.

Triphosgene (1.31 g) was added at once to a vigorously stirred mixture ofNaHCO3 (2.14 g) in water (50 ml.) and (4-bromo-phenyl)-cyclopropyl-methylamine (2.50 g) in dichloromethane (50 ml.) chilled in an ice bath. The cooling bath was removed and the mixture was stirred at room temperature for another 30 min. Then the organic phase was separated and dried (MgSO4) and the solvent was evaporated to afford the isocyanate as an oil that was directly submitted to the next reaction step. Yield: 2.88 g (quantitative); Mass spectrum (ESI ): m/z = 250/252 (Br) [M-H]”.

The synthetic route of 90868-92-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; WO2010/139673; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 138526-69-9, 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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

After adding iodine (10.0 mg, 40.0 mumol) to a tetrahydrofuran solution (190 ml) of magnesium (5.76 g, 237 mmol), 3,4,5-trifluorobromobenzene (50.0 g, 237 mmol) was added at room temperature Was slowly added dropwise.After stirring at the same temperature for 30 minutes, a tetrahydrofuran solution (160 ml) of iodine (66.1 g, 261 mmol) was added at 0 C., and the mixture was stirred at room temperature for 2 hours.The reaction mixture was poured into ice water, neutralized with concentrated hydrochloric acid, and extracted with hexane. The extract was washed with saturated aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/10) to give the title compound as a yellow oil (yield 45.0 g, yield 70%).

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, 1-Bromo-3,4,5-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hokko Chemical Industry Co., Ltd.; Suzuki, Jun; Wakabayashi, Jin; Murakami, Hideyuki; Onoue, Shinji; (19 pag.)JP2016/84348; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 25462-61-7, 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. 25462-61-7, name is 2,5-Dibromobenzene-1,4-diamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a Schienk flask, 2,5-dibromo-1,4-phenylenediamine (1 g, 3.76 mmol) and 2-(4,4,5,5-Tetramethyl-1,3,2-dioXaborolan-2-yl)-5-propylthiophene 10 (3.8 g, 15.04 mmol) were charged under the protection of nitrogen. After adding 75 ml toluene, 30 ml ethanol and 20 ml Cs2CO3 aqueous solution (2.0 mol/l), the mixture was degassed for 45 mm. Pd(PPh3)4 (435 mg, 0.376 mmol) was added. The mixture was thenheated to 80 C, stirred overnight, poured into brine and extracted by dichloromethane for several times. The organic phase was dried over Mg2SO4 and the solvent was evaporated in vacuo. The product was purified by chromatography on silica gel (CH2CI2) to give product 11 as yellow flaky crystal (860 mg, 63%). ?H NMR (400 MHz, CDCl3,. ppm): 1.00 (t, J 7.34 Hz, 6H), 1.73 (dd, .1= 15.00, 7.44 Hz, 4H), 2.80 (t, J = 7.36 Hz, 4H), 4.27-3.02 (br, 2H), 6.76 (m, 4H),7.02 (d, J = 1.96 Hz, 2H). 13C NMR (100 MHz, CDCl3, ppm): 145.9, 138.4, 136.2,125.8, 124.8, 121.9, 118.5, 32.4, 25.1, 14.0.

The synthetic route of 2,5-Dibromobenzene-1,4-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; ZHANG, Fan; WANG, Xinyang; TANG, Ruizhi; FU, Yubin; ZHUANG, Xiaodong; FENG, Xinliang; WU, Dongqing; WO2015/43722; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1753-75-9, The chemical industry reduces the impact on the environment during synthesis 1753-75-9, name is 5-Bromobenzo[c][1,2,5]thiadiazole, I believe this compound will play a more active role in future production and life.

A vial was charged with Ih (7 mg, 2 mol %) and LiCl (67.0 mg, 1.6 mmol) as necessary followed by a stirbar under an inert atmosphere. The vial was then sealed with a septum and purged under an inert atmosphere after which DME (0.8 mL) was added and the suspension was stirred until 1 h had dissolved. After this time, the organohalide (0.5 mmol) and the organomagnesium (0.8 mL, 1.0 M in THF or ether, 0.8 mmol) were added (active catalyst is indicated by the reaction solution turning orange). The septum was replaced with a Teflon-lined screw cap under an inert atmosphere and the reaction stirred at RT or warmed to 60 or 70 C. until complete. After this time, the mixture was diluted with a suitable organic solvent (15 mL) and washed successively with 1 M Na3EDTA solution (prepared from EDTA and 3 equiv of NaOH), water and brine. After drying (anhydrous MgSO4) the solution was filtered, the solvent removed in vacuo, and the residue purified by flash chromatography. A summary of the substrate scope that was explored is presented in Table 8.

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, 5-Bromobenzo[c][1,2,5]thiadiazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Total Synthesis, Ltd.; US2007/73055; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-4-(trifluoromethyl)aniline

To a 100-mLround-bottom flask was placed a solution of 2-bromo-4-(trifluoromethyl)aniline (4.8 g,20.00mmol) in THF (20 mL) then DMAP (488 mg,3.99 mmol) and Boc2O (8.72 g) were added. The reaction was heated to reflux overnight then concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtOAc/petroleum ether (1:50) affording 7.9 g of the title compound as a white solid. 1H NMR (300 MHz,CDCl3): oe 7.89 (s,1H ),7.62-7.59 (d,J = 9.0 Hz,1H ),7.38-7.35 (d,J = 9.0 Hz,1H ),1.42 (s,9H).

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 57946-63-1.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 345965-54-0, name is 1-(4-Bromophenyl)cyclopropanamine, 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 345965-54-0, name: 1-(4-Bromophenyl)cyclopropanamine

tert-Butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate In a 100-mL round bottom flask, 1-(4-bromophenyl)cyclopropan-1-amine (1 g, 4.48 mmol, 1.00 equiv) and di-tert-butyl dicarbonate (3.1 g, 13.49 mmol, 3.01 equiv) were mixed in tetrahydrofuran (20 mL), to which was added a solution of sodium bicarbonate (5 g, 59.5 mmol, 13.29 equiv) in water (10 mL) at room temperature. The resulting solution was stirred overnight at room temperature. After the reaction was done, the reaction mixture was extracted with ethyl acetate (3*10 mL) and the organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (10% to 50% gradient) to afford tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate (1.47 g, 99%) as light yellow solid. MS: m/z=255.7 [M+H-56]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)cyclopropanamine, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-52-6,Some common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

Example 4 Preparation of (3S)-methyl 3-(benzyloxycarbonyl amino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate 116.05 g trifluorobromobenzene and 400 ml tetrahydrofuran were added to a clean flask. The resulting mixture was cooled to -10 to -5 C., and then 864 ml (0.7 mol) methyl magnesium bromide was added thereto dropwisely. The mixture was stirred for 1 hour for use. 23.5 g (S)-methyl 3-(benzyloxycarbonylamino)-4-oxo n-butyrate was dissolved in 300 ml THF, and added dropwisely to the mixture mentioned above and kept at this temperature for 3 hours after completion of the addition. 400 ml solution of ammonium chloride was added dropwisely. Layers were separated. The aqueous layer was extracted with tetrahydrofuran (200 ml*2). The organic layer was dried and concentrated to get 31.4 g (3S)-methyl 3-(benzyloxycarbonylamino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate (yield: 78.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,4,5-trifluorobenzene, its application will become more common.

Reference:
Patent; Zhu, Guoliang; Zhang, Jian; Yang, Lljun; Yao, Qingdan; Ying, Jie; US2012/178957; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 57946-63-1,Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-bromo-4-(trifluoromethyl)benzenamine (1 g, 4.17 mmol, 1.00 equiv) in DMSO (20 mL), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.58 g, 6.22 mmol, 1.50 equiv), PdCl2(dppf) (91 mg, 0.12 mmol, 0.03 equiv), potassium acetate (1 g, 10.40 mmol, 2.57 equiv). The resulting solution was stirred overnight at 80¡ã C. in an oil bath. The resulting mixture was combined with the solution of the previous batch and then diluted with 100 mL of ethyl acetate. The resulting mixture was washed with 2*100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). This resulted in 1.2 g of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzenamine as a yellow solid.

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

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary