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. 34950-82-8, name is 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, A new synthetic method of this compound is introduced below., Computed Properties of C7H7BrN2O

To a solution of 7-bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (1.50 g, 6.98 mmol) in THF (10.0 mL) was added dropwise NaH (307 mg, 7.67 mmol, 60% purity) at 0C. After addition, the mixture was stirred at 0C for 30 mins, and then CH3I (1.09 g, 7.67 mmol, 478 uL) was added dropwise at 0C. The resulting mixture was stirred at 0C for 30 mins. The reaction mixture was extracted with EtOAc (10.0 mL x 3) and H2O (10.0 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give intermediate (G2.D) (1.78 g, crude) as a yellow solid which was without purfication

The synthetic route of 34950-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GenKyoTex Suisse SA; MACHIN, Peter; CHAMBERS, Mark; HODGES, Alastair; SHARPE, Andrew; WISHART, Grant; PERRY, Benjamin; CELANIRE, Sylvain; HEITZ, Freddy; (94 pag.)EP3628669; (2020); A1;,
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Reference of 61613-22-7, 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. 61613-22-7, name is 2-Bromo-N-phenylaniline, This compound has unique chemical properties. The synthetic route is as follows.

In a 200 mL three-neck flask equipped with a reflux tube, BrDPA (4.96 g, 20 mmol), di-tert-butyl dicarbonate (7.7 ml, 35 mmol), N, N-dimethyl-4-aminopyridine (0.37 g) , 3 mmol) and 150 ml of dehydrated tetrahydrofuran. The mixture was heated to reflux for about 20 hours. When the progress of the reaction was confirmed by TLC, consumption of the raw materials and spots that seemed to be the target substance were confirmed. The reaction was terminated, and the temperature was returned to room temperature. After returning to room temperature, concentration was performed. Thereafter, purification was performed by column chromatography (developing solvent ratio: n-hexane: dichloromethane = 1: 1) to obtain 5.89 g (yield = 85%) of the desired product. Identification was performed by 1H-NMR.

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

Reference:
Patent; Flask Co., Ltd.; Sasabe, Hisahiro; Kido, Junji; Arai, Hiroki; Nakao, Kohei; (21 pag.)JP2020/26399; (2020); A;,
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Application of 6274-57-3,Some common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

The synthetic route of 6274-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
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These common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, 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: 1-(4-Bromophenyl)-N-methylmethanamine

Compound 2 (1.486 g, 5.04 mmol), 4-bromo-N-methylbenzylamine (1.00 mL, 5.00 mmol) and triethylamine (1.40 mL, 10.0 mmol) were dissolved in anhydrous dimethylformamide (10 mL) and placed in a pressure bottle, under an N2 atmosphere. The reaction was heated to 130 C. for 3 days. The reaction was cooled to room temperature and diluted into deionized water (250 mL), yielding a fluffy white precipitate with a few brown clumps. After cooling briefly and sonicating and crushing the clumps, the precipitate was collected by vacuum filtration, washing with deionized water, and dried under vacuum. The crude product was dissolved in ethyl acetate and adhered to silica gel (20 g). The silica adhered compound was purified by flash silica gel chromatography (200 g silica, 3:2 hexanes:ethyl acetate) to yield 1.67 g (81%) of 14 as a white solid. ESI-MS m/z 414.1/416.1 [M+H]+. Analysis: Calcd for C20H17BrFN3O: C, 57.98; H, 4.14; N, 10.14. Found: C, 57.82; H, 4.20; N, 10.01. 1H NMR (500 MHz, DMSO-d6) delta 10.04 (s, 1H), 8.72 (s, 1H), 8.07 (d, J=9.3 Hz, 1H), 7.77-7.75 (m, 2H), 7.53 (d, J=7.0 Hz, 2H), 7.20-7.16 (m, 4H), 6.76 (d, J=9.7 Hz, 1H), 4.86 (s, 2H), 3.11 (s, 3H).

The synthetic route of 1-(4-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Syntrix Biosystems Inc.; US2012/46243; (2012); A1;,
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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. 65185-58-2, name is 2-Bromophenethylamine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromophenethylamine

General procedure: To a cooled (0 C) solution of CH2Cl2 (25 mL) and pyridine (10 mL) was added 5 (1 g, 5 mmol).The solution was stirred for five minutes followed by the addition of the acyl chloride (5 mmol, 1eq). The resulting mixture was warmed to room temperature and stirred one hour, then the solvent was removed under reduce pressure. The crude product was purified by flash chromatography with CH2Cl2.

According to the analysis of related databases, 65185-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Balieu, Sebastien; Toutah, Krimo; Carro, Laura; Chamoreau, Lise-Marie; Rousseliere, Helene; Courillon, Christine; Tetrahedron Letters; vol. 52; 22; (2011); p. 2876 – 2880;,
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Electric Literature of 1435-53-6, 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. 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 28.5 g (0.1 12 mol) 1 ,3-dibromo-4-fluorobezene, 23.5 g (0.1 12 mol) N-phenyl-1 H- benzimidazol-2-amine and 59.6 g (0.281 mol) potassium phosphate tribasic in 250 ml DMA are stirred at 160 C for 20 h under nitrogen. The reaction mixture is poured on water. The product is filtered off washed with water and ethanol. Yield 38.9 g (97.6 %). 1H NMR (400 MHz, CDCI3): delta =7.78-7.83 (m, 4H), 7.64-7.70 (m, 4H), 7.48-7.52 (m, 2 H), 7.40 (dt, 1 H), 7.33 (dt, 1 H).

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

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; KAWAMURA, Masahiro; NAGASHIMA, Hideaki; (314 pag.)WO2017/56052; (2017); A1;,
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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. 960203-41-2, name is (2-Bromophenyl)(2,4-dimethylphenyl)sulfane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of (2-Bromophenyl)(2,4-dimethylphenyl)sulfane

Intermediate 1 (Formula IV) obtained in the manner of Example 1 (10.0 g, 34 mmol),N-Boc-piperazine (7.0 g, 38 mmol) was dissolved in 50 ml of toluene.The mixture was stirred under nitrogen for 10 minutes at room temperature (25 C). To the mixture was added tris(dibenzylideneacetone)dipalladium (312 mg, 0.34 mmol),Racemic 2,2-bis(diphenylphosphino)-1,1-biphenyl (637 mg, 1.02 mmol),Sodium tert-butoxide (3.9 g, 41 mmmol),Re-nitrogen replacement.Heat to reflux under nitrogen and react for 12 h.After the reaction was completed, it was cooled to room temperature and filtered through celite.The filtrate was washed with saturated brine and toluene was removed under reduced pressure.Obtained a brown oil(N-Boc-fluoxetine) 14.2 g.

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 960203-41-2.

Reference:
Patent; Shandong Jingwei Pharmaceutical Co., Ltd.; Guo Xiao; Liu Qun; Sang Wei; Qu Aicun; Sun Huifeng; (13 pag.)CN110054600; (2019); A;,
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Application of 15155-41-6,Some common heterocyclic compound, 15155-41-6, name is 4,7-Dibromo-2,1,3-benzothiadiazole, molecular formula is C6H2Br2N2S, 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 500 ml three-necked flask equipped with a refluxing condenser, 10.0 g (FW: 293.96; 34 mmole) of 4,7-dibromobenzothiadiazole and 400 ml of ethanol as the solvent were placed. Under cooling with ice, 24.2 g (FW: 37.83; 640 mmole) of sodium borohydride was added, and the resultant mixture was sufficiently stirred for about 2 hours. When generation of a gas (hydrogen sulfide) was not observed any more, the temperature was adjusted at the room temperature, and the reaction mixture was left standing for one night (about 14 hours). Then, the solvent was completely removed under a reduced pressure, and about 400 ml of water was added to dissolve the residue. The resultant solution was left standing for one night, and the object product was recrystallized (7.17 g). The obtained product was treated by extraction with ethyl ether three times, washed with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. After diethyl ether was removed by distillation, 0.88 g of the object compound (3,6-dibromo-1,2-diaminobenzene) was obtained. The overall yield was 82%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dibromo-2,1,3-benzothiadiazole, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1749823; (2007); A1;,
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Related Products of 937046-98-5, 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 937046-98-5 as follows.

A mixture of 7-bromopyrrolo[2,l-f][l,2,4]triazin-4-amine (670.0 mg, 3.15 mmol), palladium acetate (70.6 mg, 0.31 mmol), l,3-bis(diphenylphosphino)propane (142.7 mg, 0.35 mmol), potassium carbonate (652.0 mg, 4.72 mmol), and 1-butanol (4 mL) in DMF (4 mL) was stirred under carbon monoxide at 80 0C for 4 h. The solid was filtered away and the filtrate was purified by HPLC using a gradient of 25 – 50% of MeCN in water to yield 107.3 mg (15%) of the title compound as a white solid. 1H-NMR (DMSO-J6) delta 8.28 (bs, 1 H), 8.17, (bs, 1 H), 8.05 (s, 1 H), 7.25 (d, J = 4.7 Hz, 1 H), 7.00 (d, J = 4.6 Hz, 1 H), 4.24 (t, 7 = 6.6 Hz, 2 H), 1.694.62 (m, 2 H), 1.45-1.36 (m, 2 H), 0.92 (t, J = 7.3, 3 H); MS [MH-H]+ = 235.2; LCMS RT = 2.73 min.

According to the analysis of related databases, 937046-98-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
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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. 4549-33-1, name is 1,9-Dibromononane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,9-Dibromononane

Take a 50 mL flask and install a reflux condenser.Add 2.0 mL (12.56 mmol) of 2,3,3-trimethyl-3H-indole,2.55mL1,9-dibromodecane (12.56 mmol) and 20 mL of tetrahydrofuran,Heating under reflux for 24 hours;Stop heating and allow the reaction system to cool to room temperature;1534 mg (12.56 mmol) was sequentially added to the above system.4-dimethylaminopyridine and 2.1 g (12.56 mmol) of 5-nitrosalicylaldehyde,Continue the reaction for another 5 minutes and spin dry the solvent.The product was purified by silica gel column chromatography (eluent petroleum ether / ethyl acetate).A yellow solid was obtained in an amount of 3.03 g, yield 47%.

According to the analysis of related databases, 4549-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qingdao University of Science and Technology; Deng Yawen; Xie Congxia; Wu Zhongtao; Zhang Lei; (6 pag.)CN110041341; (2019); A;,
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