Author: Jessica.F

These common heterocyclic compound, 588-96-5, name is p-Bromophenetole, 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. COA of Formula: C8H9BrO

General procedure: CS127 was prepared using a modified literature procedure [16]. A solution of butyllithium (1. hexane, 0.15 mL) was added to a solution of 4-bromotoluene (8.52 mg, 0.050 mmol) in hexane (15 mL). After stirring for 1 h, N,N’-diisopropylcarbodiimide (6.29 mg, 0.050 mmol) was added dropwise. The solution was stirred for 1 h at room temperature and then the dimer [(FMeppy)2Ir(mu-Cl)]2 (30 mg, 0.025 mmol) was added. The mixture was heated overnight at 70 C. After being cooled to room temperature, the resulting precipitate was collected and washed with diethyl ether. The dried product was obtained as a yellow powder. Yield 65%.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sahin, Cigdem; Goren, Aysen; Varlikli, Canan; Journal of Organometallic Chemistry; vol. 772; (2014); p. 68 – 78;,
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Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, belongs to ethers-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 36805-97-7, Formula: C11H25NO2

Tert-butyl 4-bromo-3-hydroxybenzoate To a solution of 4-bromo-3-hydroxybenzoic acid (1.0 g, 4.6 mmol) in toluene (100 mL) was added di-tert-butoxy-N,N-dimethylmethanamine (935 mg, 4.6 mmol). Then the mixture was stirred at 85 C. overnight. The reaction mixture was poured into water (50 mL) and ethyl acetate (50 mL), the organic phase was washed with water (30 mL), dried over anhydrous sodium sulfate, evaporated and purified by column chromatography to give tert-butyl 4-bromo-3-hydroxybenzoate (1.0 g, 79.4%) as a white solid. LRMS (M+H+) m/z: calcd 273.00. found 273.

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, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US2015/315148; (2015); A1;,
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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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, A new synthetic method of this compound is introduced below., COA of Formula: C4H9BrO2

1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone (15.5 g, 83.8 mmol), Cs2CO3 (54.6 g, 167 mmol) and 2-bromo-1,1-dimethoxy-ethane (14.78 mL, 126 mmol) was dissolved in DMF (125 mL) under an atmosphere of nitrogen. The reaction was heated to 65 C. for 6 hours. The reaction was determined to be complete by LC/MS. The reaction was taken up in EtOAc (500 mL) and washed with 5% LiCl(aq) (3*250 mL). Organics were dried over Na2SO4, filtered and solvent removed under reduced pressure. 1-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone (12.99 g, 57%) was isolated by silica gel chromatography as a white solid. LC/MS=274 (M++1)

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; Gilead Sciences, Inc.; US2011/135599; (2011); A1;,
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Synthetic Route of 578-57-4, 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. 578-57-4, name is 1-Bromo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

In a reaction tube, dissolve palladium complex [Pd] (0.03 mmol) and o-methoxybromobenzene (1.0 mmol) in 3 mL of toluene,extract and ventilate three timesin a CO2atmosphere, and connect a CO2balloonunder normal pressure. The reaction was carried out at 60 C for 8 hours. After the reaction, the reaction mixture was acidified. The reaction solution was concentrated and separated by column chromatography to obtain the corresponding product C8H8O3(yield 91%).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Institute of Technology; Yao Zijian; Chen Jing; (9 pag.)CN110483581; (2019); A;,
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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 2132-62-9 as follows. Formula: C16H14O2

General procedure: A mixture of acetophenone oxime 1a (0.2 mmol), diphenylacetylene 2 (0.24 mmol, 1.2 equiv), [Cp*IrCl2]2 (3 mol%), PivOH (0.06 mmol, 0.3 equiv), Cu(OAc)2. H2O (0.4 mmol, 2 equiv) and MeOH (2 mL) in a 15mL glass vial [sealed with poly(tetrafluoroethylene)(PTFE) cap] was heated at 120 C with vigorous stirring for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through Celite. The filtrate was concentrated in vacuo and purified by column chromatography on silica gel to give the corresponding product 4.

According to the analysis of related databases, 2132-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Wei; Hu, Xiu-Xiu; Zhuang, Cang-Wei; Wang, Ya-Zhen; Tetrahedron; vol. 75; 22; (2019); p. 3015 – 3023;,
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Application of 1159512-64-7,Some common heterocyclic compound, 1159512-64-7, name is 2-Fluoro-3-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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 (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (1 equiv) in DMF (10 vol) at 0 C. under nitrogen atmosphere was added 2-fluoro-3-(trifluoromethoxy)aniline (1.2 equiv), HBTU (1.5 equiv) and DIPEA (3 equiv). The reaction mixture was stirred at room temperature for 12 h. After completion of the reaction, the reaction mixture was quenched with water. The resulting mixture was extracted with DCM. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and then concentrated. The residue was purified by column chromatography on silica gel using DCM/MeOH to give compound 1239.

The synthetic route of 1159512-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, belongs to ethers-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 54314-84-0, category: ethers-buliding-blocks

Reference Example 9[4-(3-Benzyloxypropoxy)-2-methylphenyl]methanol To a solution of 4-bromo-3-methylphenol (2.5 g) inN,N-dimethylformamide (10 mL) were added cesium carbonate (4.79 g), benzyl 3-bromopropyl ether (2.48 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 60 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(3-benzyloxypropoxy)-1-bromo-2-methylbenzene. This material was dissolved in tetrahydrofuran (100 mL). To the solution was added n-butyl lithium (2.46 mol/Ln-hexane solution, 6 mL) at -78°C under an argon atmosphere, and the mixture was stirred for 5 minutes. To the reaction mixture was added N,N-dimethylformamide (2.57 mL), and the mixture was allowed to warm to 0°C and stirred for 1 hour. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(3-benzyloxypropoxy)-2-methylbenzaldehyde. This material was dissolved in ethanol (40 mL). To the solution was added sodium borohydride (506 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added methanol, and the resulting mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 5/1 – 1.5/1) to give the title compound (3.33 g).1HNMR (CDCl3) delta ppm: 1. 37 (1H, t, J=5.7Hz), 2.0-2.15 (2H, m), 2.36 (3H, s), 3. 66 (2H, t, J=6.2Hz), 4.08 (2H, t, J=6.3Hz), 4.52 (2H, s), 4.63 (2H, d, J=5.7Hz), 6.65-6.8 (2H, m), 7.15-7.4 (6H, m)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1548024; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, belongs to ethers-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 89282-70-2, Recommanded Product: 89282-70-2

A mixture of phenyl 5-({trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}carbamoyl)-1 H-imidazole-4-carboxylate (150 mg, 0.309 mmol,) and 2-methoxy-2-methylpropan-1 -amine(160 mg, 1.55 mmol, GAS No 89282-70-2) in tetrahydrofuran (4.8 ml) was stirred at 600over night. For work-up, the reaction mixture was concentrated and the residue was purified by flash chromatography (25 g Snap Cartridge, ethyl acetate/ethanol gradient, 0% -> 5% ethanol) to yield the title compound (18.0 mg, 12 yield).[C-MS (Method 6): R = 1 .08 mm; MS (ESIpos) m/z = 494.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 13.20-12.45 (m, 1H), 11.43-1 0.70 (m, 1H), 9.52 (s,1H), 8.69-7.89 (m, 1H), 7.82 (s, 1H), 7.65-7.57 (m, 1H), 7.53-7.47 (m, 1H), 7.27-7.18 (m,1H), 3.89-3.66 (m, 1H), 3.37 (d, 2H), 3.15 (s, 3H), 2.48-2.38 (m, 1H), 2.10-1.75 (m, 4H),1.71 -1 .32 (m, 4H), 1.14 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methoxy-2-methylpropan-1-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

Step A: methyl 2-cyanoacetate (23 g, 232 mmol) was addeddropwise to a suspension of sodium hydride (60percent, 2.79 g,69.7 mmol) in DMF (100 mL) and THF (100 mL) at 0 C, and thereaction mixture was warmed to rt and stirred at rt for 30 min.((2-Bromoethoxy)methyl)benzene (10 g, 46.5 mmol) was added,and the reaction mixture was stirred at rt for 12 h. Water wasadded and the aqueous layer was extracted with ether (3). Thecombined organic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was evaporatedto give the crude product. Excessive methyl 2-cyanoacetate wasremoved by distillation under high vacuum at 120?130 C, andremaining residue was purified by silica gel chromatography elutingwith 0?50percent EtOAc/hexanes to give methyl 4-(benzyloxy)-2-cyanobutanoate (8 g, 74percent) as a colorless liquid. 1H NMR(300 MHz, CDCl3) d 7.3 (m, 5H), 4.51 (s, 2H), 3.70 (s, 3H), 3.6?3.9(m, 3H), and 2.3 (m, 2H). LC/MS m/z: (M+H)+ calcd forC13H16NO3, 234.11; found 234.4. Step B: To a suspension of sodiumhydride (60percent, 9 g, 225 mmol) in THF (170 mL) and DMF (170 mL)was added methyl 4-(benzyloxy)-2-cyanobutanoate (35 g,150 mmol) at 0 C, and the reaction mixture was stirred at rt for30 min. ((3-Bromopropoxy)methyl)benzene (37.8 g, 165 mmol)was added, and the reaction mixture was stirred at rt for 12 h.Water was added and the aqueous layer was extracted with ether(3). The combined organic layers were washed with brine, driedover anhydrous sodium sulfate, and filtered, and the filtrate wasevaporated to give the crude product. The crude product was purifiedby silica gel chromatography eluting with 0?40percent EtOAc/hexanesto give 22 (40 g, 70percent) as a colorless oil. 1H NMR (400 MHz,CDCl3) d 7.3 (m, 10H), 4.48 (2H, s), 4.47 (2H, s), 3.7 (m, 2H), 3.57(3H, s), 3.48 (m, 1H), 2.42 (m, 1H), 1.8?2.1 (m, 4H), and 1.6 (m,1H). LC/MS m/z: (M+H)+ calcd for C23H28NO4, 382.20; found 382.4.

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:
Article; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
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Adding a certain compound to certain chemical reactions, such as: 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, belongs to ethers-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 6851-80-5, Application In Synthesis of 1-(2-Methoxyphenyl)-N-methylmethanamine

General procedure FStep 1 / synthesis of substituted N-benzyl-4-chloro-N-methylbutanamide : Triethylamine (1 eq) and 4-chlorobutyryl chloride (1 eq) were added to a solution of the substituted N-methylbenzylamine (1 eq) in dichloromethane (1.3 ml_/ mmol). The mixture was stirred 3 hours at room temperature then water was added. The resulting mixture was extracted 3 times with dichloromethane, the combined organic layers were dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel) with the appropriate gradient determined by TLC to give the substituted N-benzyl-4-chloro-N-methylbutanamide. Step 2 / alkylation of thiols with substituted N-benzyl-4-chloro-N-methylbutanamide: Anhydrous potassium carbonate (1.5eq) and substituted N-benzyl-4-chloro-N- methylbutanamide (1 eq) were added to a solution of the thiol derivative (1 eq) in acetonitrile (6 mL / mmol). The mixture was refluxed overnight then water and ethyl acetate was added after cooling. The mixture was extracted 3 times with ethyl acetate, the combined organic layers were washed with brine, dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel) with the appropriate gradient determined by TLC to give the thio-ether.The following compounds were prepared according general procedure F :Example 138 : 4-[(3,4-Difluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamidePrepared from commercial 3,4-difluorothiophenol and commercial 2-methoxy-N- methylbenzylamine in 27% yield.NMR-1H (CDCI3) : delta (ppm) 7.32-6.85 (m, 7H) ; 4.55 (d, 2H) ; 3.84-3.82 (m, 3H) ; 3.03-2.92(m, 5H) ; 2.50 (t, 2H) ; 2.04-1 .94 (m, 2H) MS (ESI+) : m/z = 366 [M+H]+

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-(2-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELLVIR; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S); BENAROUS, Richard; BARBEY-TREVE, Sabine; PARIS, Jean-Marc; BERRUT, Sebastien; BERLIOZ-TORRENT, Clarisse; EMILIANI, Stephane; WO2010/66847; (2010); A1;,
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