Tag: M.W=200-300

Some common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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. Formula: C5H10Br2O2

3 ,3 -dimethoxy- 1 – [4-(trifluoromethoxy)phenyl]cyclobutanecarboxamide [1291] 2-[4-(Trifluoromethoxy)phenyl]acetonitrile (7.86 mL, 50 mmol), 1,3- dibromo-2,2-dimethoxypropane (13.10 g, 50.0 mmol), and sodium tert-butoxide (10.57 g, 1 10 mmol) were dissolved in DMSO (100 mL) and water (5 mL), and the mixture was heated for 1 hour at 125 C. The reaction was cooled to ambient temperature and stirred overnight. The reaction mixture was diluted with water and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried with MgS04, filtered, and concentrated to give the title compound (17.02 g, 53.3 mmol, 107% yield). MS (DCI+): m/z 320.1 (M+H), 337.1 (M+NH4). XH NMR (300 MHz, DMSO-d6) ? 7.44 (d, J= 8.8 Hz, 2H), 7.34 (s, 1H), 7.31 (d, J= 8.8 Hz, 2H), 6.90 (s, 1H), 3.05 (s, 3H), 3.02 – 2.93 (m, 5H), 2.41 (d, J= 13.4 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22094-18-4, its application will become more common.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-2-(trifluoromethoxy)aniline

General procedure: A solution of substituted anilines (12.4 mmol) dissolved in 30 mL anhydrous THF was added very slowly into a stirred solution of triphosgene (1.40 g, 4.80 mmol) in 20 mL of THF. After stirringfor 15 min, triethylamine (2.90 mL, 20.6 mmol) was then added slowly to the reaction mixture. Stirring was continued for 20 min, various aromatic heterocyclic amines (12.0 mmol) in anhydrous THF (20 mL) was added directly to the above residue. After completion of the action, the reaction was quenched with dilute NaHCO3 and the solvent was subsequently removed in vacuo and extracted with ethyl acetate (3 30 mL). The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silicagel flash chromatography (PE/AcOEt = 5:1) gave as white solid (3a-3h) (yield: 30-50%).

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 886762-08-9.

Reference:
Article; Shan, Yuanyuan; Wang, Chen; Zhang, Lin; Wang, Jinfeng; Wang, Maoyi; Dong, Yalin; Bioorganic and Medicinal Chemistry; vol. 24; 4; (2016); p. 750 – 758;,
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These common heterocyclic compound, 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, 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. Formula: C8H9BrO2

EXAMPLE 214 1,2-Dihydro-9-methoxy-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 314, structure 41 of Scheme XI, where R1 =H, R2 =methoxy) 2,5-Dimethoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =methoxy) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 1-bromo-2,5-dimethoxybenzene (2.00 mL, 13.3 mmol), n-BuLi (2.5 M in hexanes; 5.34 mL, 13.3 mmol), and trimethylborate (4.5 mL, 40 mmol) to afford 2.43 g (99%) of 2,5-dimethoxyphenylboronic acid which was used without further purification.

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

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;,
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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. 7025-06-1, name is 1-Bromo-2-phenoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2-phenoxybenzene

31.7 g (127 mmol) of1-Bromo-2-diphenyl ether,Dissolve in 400 ml of anhydrous THF in a flask which has been dried by heating. Cool the reaction mixture to -78 ¡ã C. At this temperature 55 ml of a 2.5 M solution of n-BuLi in hexane (127 mmol) is slowly added dropwise.The batch was further heated at -70 ¡ã C.Stir for 1 hour.30 g of 2-bromofluorenone (116 mmol)Is dissolved in 100 ml of THF and added dropwise at -70 ¡ã C.Upon completion of the addition, the reaction mixture is warmed slowly to room temperature, warmed up using NH 4 Cl, then evaporated in a rotary evaporator.

The synthetic route of 7025-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; MUJICA-FERNAUD, TERESA; MONTENEGRO, ELVIRA; VOGES, FRANK; KROEBER, JONAS VALENTIN; STOESSEL, PHILIPP; (98 pag.)JP2016/505518; (2016); A;,
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36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, belongs to ethers-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. Product Details of 36449-75-9

Compound 12. l ,4-bis(2-methoxyphenethyl)piperidine A 250 mL round bottom flask was equipped with a magnetic stir bar, and then charged with 5 grams (0.0537 mol) of 4-picoline, 8.77 grams (0.0644 mol) of 2- methoxybenzaldehyde, and 50 mL of acetic anhydride. The reaction mass was heated to reflux and maintained at that temperature for 72 hours. The reaction mixture was then cooled to room temperature, and subjected to silica chromatography. Yield of (E)-4-(2- methoxystyryl)pyridine was 7.15 grams (63%). The 7.15 grams of (E)-4-(2- methoxystyryl)pyridine was then charged into a 500 ml hydrogenation flask, to which was added 100 mL of acetic acid as well as 50 mg of Pt02. The reaction mass was subjected to 45 psi of hydrogen gas, and allowed to react at room temperature for 16 hours. The reaction mixture was then basified, and extracted with dichloromethane, and excess extraction solvent was removed under reduced pressure via rotovap. The residue was then subjected to silica chi matography, yielding 6.1 grams (82.1% yield) of 4-(2-methoxyphenethyl)piperidine. A 100 mL round bottom flask equipped with a magnetic stir bar was then charged with 1.0 grams of 4-(2-methoxyphenethyl)piperidine (0.0046 mol), 1.25 grams of 2- methoxyphenethylbromide (0.0064 mol), 1.87 grams of K2CO3 (0.0135 mol), and 20 mL of DMF as solvent. The reaction mass was then heated to 70 C for 24 hours. The excess DMF was removed via reduced pressure, extracted with water and dichloromethane, the organic layer separated; excess solvent removed under reduced pressure and the residue was subjected to silica chromatography. Yield of l,4-bis(2-methoxyphenethyl)piperidine was 1.04 grams (64.0% yield). 1H NMR (300 MHz, CDC13) delta 1.33-1.59 (m, 7H), 2.35-2.80 (m, 10H), 3.82 (s, 6H), 6.83-7.21 (m, 8H) ppm.

The synthetic route of 36449-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; CROOKS, Peter, A.; DWOSKIN, Linda, P.; CULVER, John; NICKELL, Justin, R.; ZHENG, Guangrong; WO2014/144064; (2014); 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. 15268-07-2, name is 3,3′-Oxydianiline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 15268-07-2

To a suspension of p-toluenesulfonic acid hydrate (30.8 g, 162 mmol) in tert-butylalcohol (110 mL) and water (5 mL) was added 3,3?-oxydianiline (3.6 g, 17.9 mmol) and the reaction mixture cooled to 10 C. in an ice/water bath. A solution of sodium nitrite (7.4 g, 108 mmol) and potassium iodide (22.4 g, 135 mmol) in water (30 mL) was added dropwise over 1 hour, keeping the temperature below 15 C. The cold bath was removed and the reaction mixture allowed to warm to room temperature and stirred for another 3 hours. To the reaction mixture was added 15 g NaHCO3 to pH 8 followed by 35 g Na2S2O3 and the mixture stirred for 30 minutes before being poured into 300 mL of water. The mixture was extracted 2¡Á100 mL with ether and 3¡Á100 mL DCM. The combined extracts were washed with 2¡Á100 mL water, dried over sodium sulfate and evaporated leaving 4.5 g of a dark liquid. The crude oil was chromatographed on silica with hexane to give 4.8 g (79%) of 3,3?-oxybis(iodobenzene) as a white solid. The product was confirmed by GC/MS and NMR.

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 15268-07-2.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; Tsai, Jui-Yi; Kottas, Gregg; Brooks, Jason; Yeager, Walter; Ansari, Nasrin; Barron, Edward; Xia, Chuanjun; (126 pag.)US9461254; (2016); B2;,
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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 886762-08-9 as follows. Computed Properties of C7H5BrF3NO

10.74 g (93.75 mmol) of tert-butyl nitrite and 28.5 g (150 mmol) of copper iodide are suspended in 270 ml of acetonitrile and heated to 60 C. A solution of 15 g (62.5 mmol) of 5-bromo-2-trifluoromethoxyaniline in 130 ml of acetonitrile is slowly added dropwise to this suspension and the mixture is left to stir at 60 C. for another hour. The reaction solution is then poured on to a mixture of 250 ml of 2 N aqueous HCl and 250 ml of ethyl acetate. The organic phase is washed twice more with aqueous NaCl solution, filtered through a little silica gel and concentrated. The residue is separated by chromatography on silica gel (ethyl acetate/n-heptane=1/18). This affords 12.2 g (52% yield) of product 96 as a colorless oil.

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2011/59910; (2011); A1;,
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Some common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, molecular formula is C7H6BrFO, 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: 446-59-3

2-Bromo-3-fluoro anisole (10 g, 48.77 mmol) was dissolved in DCM (200 mL) and cooled to about -78 C. To the solution was added BBr3 (11.53 mL, 121.9 mmol) in one portion. The mixture was warmed to r.t. and stirred overnight. The mixture was partitioned between water and DCM (50 mL), and the aqueous layer was back extracted with DCM (200 mL). The combined organics were dried (NaSO4), filtered and concentrated to give about 9.32 g of the product as a dark oil. MS found 188.9 (M-1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 446-59-3, its application will become more common.

Reference:
Patent; Briner, Karin; Doecke, Christopher William; Mancuso, Vincent; Martinelli, Michael John; Richardson, Timothy Ivo; Rothhaar, Roger Ryan; Shi, Qing; Xie, Chaoyu; US2004/82590; (2004); A1;,
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Reference of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Intermediate 8 (1.70 g, 8.015 mmol) was dissolved in N, N-dimethylformamide (20 mL)Placed in a sealed tube,2,2′-dibromodiethyl ether (1.4 mL, 8.816 mmol) and N, N-diisopropylethylamine (2.7 mL, 16.03 mmol) were added.The reaction was heated to 100 C,Stir for 16 hours.Cooled to room temperature,Ethyl acetate was added,Washed,The organic phase is dried,Filtered and concentrated under reduced pressure,The crude product was purified by column chromatography,To give intermediate 9 (2.23 g) in 42% yield.

Statistics shows that 1-Bromo-2-(2-bromoethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 5414-19-7.

Reference:
Patent; Shanghai Hansoh BioMedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Zhao, Zhiming; Wu, Chenchen; Yu, Hongping; Xu, Yaochang; Pan, Zhongzong; Bao, Rudi; (26 pag.)CN106349180; (2017); A;,
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Related Products of 89521-55-1, A common heterocyclic compound, 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, molecular formula is C13H14N2O, 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 solution of Compound (6) (1.0 g), 3-(benzyloxy)-1,2-benzenediamine (817 mg) and 1-hydroxybenzotriazole (567 mg) in N,N-dimethylformamide (19 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (804 mg). After stirring for 6 hrs, saturated aqueous NaHCO3 (20 mL) and water (80 mL) were added to the reaction mixture. The resulting precipitate was collected by filtration and washed with water. To a mixture of this product in acetic acid (7 mL) was added a solution of hydrogen chloride in acetic acid (13 mL). After stirring at 100 C. for 1 hour, the resulting mixture was cooled to 4 C. and diluted with ethyl acetate (40 mL). The resulting precipitate was collected by filtration and washed with ethyl acetate. To a solution of this product, O-tetrahydro-2H-pyran-2-ylhydroxylamine (1.5 eq.) and 1-hydroxybenzotriazole (1.5 eq.) in N,N-dimethylformamide (11 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.5 eq.) at 4 C. The mixture was warmed to ambient temperature and stirred for 8 hrs. The reaction mixture was added saturated NaHCO3 (11 mL) and water (44 mL). A resulting precipitate was filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was treated with trifluoroacetic acid to give Compound E120 (52 mg). 1H-NMR (300 MHz, DMSO-d6, delta): 4.43 (2H, s), 6.46 (1H, d, J=16 Hz) 6.86 (1H, d, J=8 Hz), 7.12(1H, d, J=8 Hz), 7.23-7.30 (1H, m), 7.39-7.62 (5H, m);

The synthetic route of 89521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; US2004/229889; (2004); A1;,
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