Tag: M.W=200-300

Application of 32338-02-6, A common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-methoxyaniline, molecular formula is C7H8BrNO, 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.

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 °C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

The synthetic route of 32338-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Electric Literature of 168268-00-6, A common heterocyclic compound, 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, molecular formula is C13H12FNO, 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 stirred mixture of 4-benzyloxy-3-fluoro-phenylamine (155.3 mmol, 33.7 g), 1- (4-FLUORO-PHENYLCARBAMOYL)-CYCLOPROPANECARBOXYLIC acid (170.8 mmol, 38.13 g) and anhydrous dichloromethane (600 ml) was added EDCI (233.9 mmol, 44.7 g) in portions. After stirring at RT for 1 hr, the reaction mixture was diluted with saturated sodium bicarbonate (400 ml) and stirred for 30 minutes. The precipitate was filtered and air dried to give the 1ST CROP of product. The biphasic filtrate was separated, and the organic phase was washed with brine (300 ml), dried over sodium sulfate, and concentrated. The residue was taken up in DCM (100 ml), stirred for 15 minutes, and filtered to give a 2ND crop of product. The combined yield of cyclopropane-1, 1- dicarboxylic acid (4-benzyloxy-3-fluoro-phenyl) -amide (4-fluoro-phenyl) -amide was 64.5 g (98%).

The synthetic route of 168268-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; WO2005/30140; (2005); A2;,
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Related Products of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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 24 Synthesis of (1R,10R,11S,16S)-1,11,15,15-tetramethyl-3,5-bis(propan-2-yloxy)-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene To a solution of (35) (15.0 g, 69.0 mmol) in CH2Cl2 (40 mL), cooled to 0 C., a 1 M BBr3 solution in CH2Cl2 (140 mL, 140 mmol) was added dropwise. The ice bath was removed and the reaction was stirred at room temperature for 18 h. The reaction was quenched with MeOH and concentrated. The residue was dissolved in EtOAc (500 mL) and washed with water (300 mL). The organic layer was separated, dried (Na2SO4) and concentrated to give 5-bromobenzene-1,3-diol (45) (13.03 g, >99%) as an orange oil.

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aquinox Pharmaceuticals Inc.; US2011/136802; (2011); A1;,
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Synthetic Route of 17061-62-0, 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. 17061-62-0, name is Bis(4-methoxybenzyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0407j N,N-bis(4-methoxybenzyl)methanesulfonamide, Example 13.0. To a solution of bis(4-methoxybenzyl)amine 12.01 (100 g, 0.389 mol, 1 eq) in DCM (1 L) was added TEA (71 mL, 0.506 mol, 1.3 eq) followed by dropwise addition of methanesulfonyl chloride (36 mL, 0.46 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the methane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. Water (1 L) was added to the reaction. The layers were separated and the aqueous layer was extracted with DCM (2x 500 mL). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was absorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10-80% EtOAc in hexanes) to provide 120 g (0.36 mol, 92%) of the title compound Example 13.0 as white solid. ?H-NMR(400 MHz, CDC13) 7.26 (dd, J= 2.12, 6.60 Hz, 4H), 6.91 (dd, J= 2.12, 6.62 Hz, 4H), 4.28 (s, 4H), 3.83 (s, 6H), 2.75 (s, 3H). GC-MS (ESI p05. ion) mlz: = 335 (M+H).

The synthetic route of Bis(4-methoxybenzyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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These common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)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. Recommanded Product: 5-Bromo-2-(trifluoromethoxy)aniline

General procedure: To a solution of N-tosylhydrazone (0.6mmol, 1.1 eq) in distilled dioxane (8mL) was added bis(acetonitrile)palladium(II) chloride (0.05mmol, 5mol %), and dppp (0.1mmol, 10mol %). The resulting suspension was stirred RT for 2min, and cesium carbonate (1.5mmol, 3.0 eq) was added. Then, the reaction mixture was stirred for additional 2min, and aryl bromide (0.5mmol, 1.0 eq) was added in one portion. The mixture was then heated at 100C for 3h. The crude reaction mixture was allowed to cool to rt. EtOAc was added, and the mixture was filtrated through Celite. The solvent was evaporated under reduced pressure, and the crude product was purified by flash chromatography on silica gel.

The synthetic route of 5-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naret, Timothee; Bignon, Jerome; Bernadat, Guillaume; Benchekroun, Mohamed; Levaique, Helene; Lenoir, Christine; Dubois, Joelle; Pruvost, Alain; Saller, Francois; Borgel, Delphine; Manoury, Boris; Leblais, Veronique; Darrigrand, Romain; Apcher, Sebastien; Brion, Jean-Daniel; Schmitt, Etienne; Leroux, Frederic R.; Alami, Mouad; Hamze, Abdallah; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 473 – 490;,
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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. 588-63-6, name is (3-Bromopropoxy)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C9H11BrO

2,4-diamino-5-hydroxy -1, 3, 5-tri-aza-9-oxa-spiro [5.5] undecane -1,3-diene-hydrochloride (0.47g, 0 . 002mol), sodium hydroxide (0.08g, 0 . 002mol), methanol 10 ml in mixed in the round-bottom flask, heating to reflux 30 minutes, the heat filters, concentrating the filtrate. By adding 1-bromo-3-phenoxy-propane (0.52g, 0 . 0024mol) and DMF2ml, stirring the mixture at room temperature. When consumes TLC monitoring raw materials, into a small amount of thick hydrogen PH value in order to adjust the bromate 2-3. Remove the solvent under reduced pressure, to obtain white solid, with ethanol: water = 10:1 ( volume ratio ) recrystallization, get white crystal 0.26g, yield 31.7percent, HPLC purity measured 99.6percent.

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; Shanghai Institute Of Pharmaceutical Industry(China State Institute of Pharmaceutical Industry); zhou, xiaotian; lin, kuaile; zhou, Weicheng; (41 pag.)CN103664972; (2016); B;,
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Reference of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.

Step3. 4-(4-morpholinyl)-1-{3-[(phenylmethyl) oxy] phenyl}-1-butanone Under argon, to a solution of 1-bromo-3-[(phenylmethyl) oxy] benzene (2.04 g, 7.76 mmol) in THF (30 mL) at-78 C, was added dropwise n-BuLi (5.1 mL, 1.6 M in Hexanes), 20 min after the addition, this solution was added to a solution the product from Step 3 (1.68 g, 7.76 mmol) in THF (30 mL) under argon at-78 C. 15 min later, the reaction mixture was slowly warmed to 0 C. The reaction mixture was poured into a mixture of EtOAC and NH4C1, then extracted with EtOAC (2X), organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was then purified with flash chromatography (hexanes/ethyl acetate 1: 4), to afford the title compound as a colorless oil (932 mg, 35%).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/37197; (2005); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H13BrO

Magnesium (317.2 mg, 13.05 mmol) was suspended in 5 mL of ether, a solution of 2.30 mL (13.0 mmol) of 3-benzyloxypropyl bromide in 7 mL of ether was dropped into the suspension over 10 minutes, a flake of iodine was added thereto and the mixture was heated to reflux for 1 hour. The reaction mixture was cooled with an ice-methanol bath, a solution of 5.1 mg (0.011 mmol) of N-methoxy-N-methyl-(1-methylindole)-2-carboxamide in tetrahydrofuran was added thereto and the mixture was stirred at 0°C for 2 hours. Ice water was added to the reaction solution and the mixture was acidified with 6 mol/L hydrochloric acid and extracted with ether. The organic layer was washed with water and a saturated aqueous saline solutio dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate = 8/1) to give 0.79 g (54percent) of 2-(4-benzyloxy-1-oxobutyl)-1-methylindole.1H-NMR(270MHz, DMSO-d6, delta); 2.09(m, 2H), 3.10(t, J=7.3Hz, 2H), 3.58(t, J=6.1Hz, 2H), 4.05(s, 3H), 4.50(s, 2H), 7.15(m, 1H), 7.26-7.39(m, 8H), 7.69(dd, J=1.0Hz, 8.3Hz, 1H). Fab-MS(m/z); 308[M+1]+

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 54314-84-0.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1464645; (2004); A1;,
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Synthetic Route of 886762-08-9, The chemical industry reduces the impact on the environment during synthesis 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General procedure: Triphosgene (0.74 g, 2.5 mmol) was dissolved in anhydrousCH2Cl2 (20 mL) and the mixture was stirred on the ice-bath for15 min. A solution of the [3-bromo-5-(trifluoromethyl)phenyl]amine (1.66 g, 6.9 mmol) in anhydrous CH2Cl2 (10 mL) was addeddropwise to the above mixture and stirring continued for 30 min.Then triethanolamine (0.75 mL, 5.5 mmol) diluted with CH2Cl2(10 mL) was then added into the mixture. Stirring was continuedfor 20 min, a solution of triethanolamine (0.75 mL, 5.5 mmol) andintermediate (4a) (1.50 g, 6.3 mmol) in anhydrous CH2Cl2 (10 mL)was added. After completion of the action, the reaction wasquenched with dilute NaHCO3. The organic layer was washed withwater and brine, and dried over Na2SO4. After filtration and concentrationin vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt 5:1) gave as white solid (5a) (1.36 g,43%).

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-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shan, Yuanyuan; Gao, Hongping; Shao, Xiaowei; Wang, Jinfeng; Pan, Xiaoyan; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 80 – 90;,
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Electric Literature of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

A flask containing tetrahydrofuran (5.0 niL) was charged with sodium amide (109 mg, 2.65 mmol; Alfa Aesar), chilled to 0 0C, and treated with 2,1 l-dimethyl-5,6,7,8,9,10- hexahydro-7,10-epiminocyclohepta[delta]indole (300 mg, 1.326 mmol; Example IA), added in portions. After 5 minutes, the ice bath was removed and the mixture was heated to 60 0C for 15 minutes. The solution was cooled to room temperature and l-(2-bromoethoxy)-4- fluorobenzene (348 mg, 1.591 mmol; Aldrich) was added slowly. The reaction mixture was stirred overnight at room temperature, then diluted with water (5 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated in vacuo, and the resulting residue was purified by reverse- phase HPLC (Phenomenex Luna C8(2) 5 mum IOOA AXIA column, 30×75 mm, 10-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid, flow rate 50 mL/minute) to afford the title compound as the trifluoroacetic acid salt: 1H NMR (300 MHz, methanol-^) delta ppm 1.79 – 2.07 (m, 1 H), 2.12 – 2.30 (m, 1 H), 2.34 – 2.50 (m, 4 H), 2.50 – 2.66 (m, 1 H), 2.93 (s, 3 H), 3.02 – 3.20 (m, 1 H), 3.66 (d, J=17.1 Hz, 1 H), 4.13 – 4.37 (m, 3 H), 4.42 – 4.58 (m, 2 H), 4.93 – 5.12 (m, 1 H), 6.61 – 6.84 (m, 2 H), 6.81 – 7.01 (m, 2 H), 7.01 – 7.14 (m, 1 H), 7.31 (s, 1 H), 7.34 – 7.43 (m, 1 H); MS (ESI) m/z 365 (M+H)+.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; SCHRIMPF, Michael R.; LEE, Chih-Hung; LI, Tao; GFESSER, Gregory A.; MORTELL, Kathleen H.; FAGHIH, Ramin; NERSESIAN, Diana L.; SIPPY, Kevin B.; BUNNELLE, William H.; SCANIO, Marc; SHI, Lei; GOPALAKRISHNAN, Murali; DONNELLY-ROBERTS, Diana; HU, Min; WO2010/36998; (2010); A2;,
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