Month: August 2021

Application of 332-48-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 332-48-9 name is 1-(2-Bromoethoxy)-4-fluorobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A suspension of N-Boc- (L)-dopa 67.27 mmol), 2-(4- fluorophenoxy) ethyl bromide (0.95 eq) and potasium bicarbonate (1.1 eq) in DMA (100 mL) was stirred at 65 C overnight. The reacted mixture was diluted with EtOAc (750 mL), washed with water (2×200 mL) and saturated NaHC03 (2×200 mL), brined, dried over Na2S04, concentrated under reduced pressure, and purified by column chromatography on silica gel (60 A, 200-400 Mesh) eluting with 3:7 EtOAc/Hexane to give a clear oil. [00176] The oil was dissolved in a solution of HCl/1,4-dioxane (4.OM, 100 mL), and the mixture was stirred at room temperature for 1 hour before concentrating under reduced pressure to a solid. After dissolving the solid in a minimal amount of acetonitrile (100 mL), the solution was chilled to 4 C, and the resulting white precipitate was collected on a Buchner funnel, washed with diethyl ether (3×50 mL) and dried under high vacuum to afford the title compound as a solid: ¹H NMR (d6-DMSO) : No. 2.92 (m, 2H), 4.14 (m, 2H), 4.21 (t, J = 6.4 Hz, 1H), 4.42 (t, J = 4.4 Hz, 2H), 6.43 (d, J = 7.6 Hz, 1H), 6.59 (s, 1H), 6.60 (d, J = 8.0 Hz, 1H), 6.94 (m, 2H), 7.12 (3, 2H), 8.40 (s, 3H), 8.90 (m, 2H). MS (ESI) m/z 336 (M+H) (at) and 334 (M-H)-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethoxy)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; XENOPORT, INC.; WO2005/121070; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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 93919-56-3, name: (4-(Trifluoromethoxy)phenyl)methanamine

General procedure: To a solution of 4 (290mg, 1.02mmol) in DMF (1.5mL), CDI (198mg, 1.23mmol) was added under N2 protection. The resulting reaction was stirred 50C. After 2h, the mixture was cooled to room temperature, and the corresponding benzylamine (1.53mmol) was added. The resulting reaction was stirred 50C under N2 protection overnight. Then the mixture was cooled to room temperature, quenched with 1M hydrochloric acid, diluted with water (50mL), and extracted with CH2Cl2 (60mL×3). The combined organic layer were washed with saturated solution of NaCl (60mL×3), dried over MgSO4, concentrated and purified by flash chromatography eluting with 5-50% ethyl acetate in petroleum ether, to provide the desired products 5a-5d.

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

Reference:
Article; Liu, Siming; Jiang, Ying; Yan, Ruohong; Li, Zhonghuang; Wan, Shanhe; Zhang, Tingting; Wu, Xiaoyun; Hou, Ju; Zhu, Zhengguang; Tian, Yuanxin; Zhang, Jiajie; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 358 – 375;,
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Synthetic Route of 2132-62-9, 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. 2132-62-9, name is 1,2-Bis(4-methoxyphenyl)ethyne belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 5 Preparation of 3,4-Bis(4-methoxyphenyl)-1-ethoxybenz[c-1,2]oxaphosphinine 1-oxide 3,4-Bis(4-methoxyphenyl)-1-ethoxybenz[c-1,2]oxaphosphinine 1-oxide (57.0 mg, 90%) as a target compound was obtained under the condition of 90 C. for 12 hours, by the same reaction as the Example 1 above, except for using 1,2-bis(4-methoxyphenyl)ethyne (54.0 mg, 0.23 mmol) instead of using diphenylacetylene of the Example 1 above. 1H NMR (400 MHz, CDCl3) delta 7.95-7.89 (m, 1H), 7.48-7.43 (m, 1H), 7.41-7.37 (m, 1H), 7.19 (dt, J=9.17 Hz, 2.56 Hz, 2H), 7.14-7.10 (m, 2H), 7.00-6.96 (m, 1H), 6.93-6.89 (m, 2H), 7.19 (dt, J=9.20 Hz, 2.52 Hz, 2H), 4.30-4.15 (m, 2H), 3.84 (s, 3H), 3.75 (s, 3H), 1.31 (t, J=4.82 Hz, 3H)

The synthetic route of 1,2-Bis(4-methoxyphenyl)ethyne has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KNU-INDUSTRY COOPERATION FOUNDATION; Lee, Phil Ho; Park, Young Chul; Jeon, In Cheol; Seo, Jung Min; Seo, Bo Ram; US2015/344506; (2015); A1;,
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Reference of 2132-62-9,Some common heterocyclic compound, 2132-62-9, name is 1,2-Bis(4-methoxyphenyl)ethyne, molecular formula is C16H14O2, 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 a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Bis(4-methoxyphenyl)ethyne, its application will become more common.

Reference:
Article; Shu, Zhen; Guo, Yuntao; Li, Wei; Wang, Baiquan; Catalysis Today; vol. 297; (2017); p. 292 – 297;,
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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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6298-96-0

Example II (S)-4-(1-Amino-ethyl)-phenol hydrobromid To 11.0 g (72.7 mmol) (S)-1-(4-methoxy-phenyl)-ethylamine is added carefully 30 mL HBr (30% in HOAc). The mixture is stirred at 100 C. for 4 h. After cooling down to r.t., the solvent is removed in vacuo and the residue is dried in vacuo. The resulting product is used without further purification. C6H11NO*HBr (M=218.1 g/mol) ESI-MS: 121 [M+H-NH3]+Rt (HPLC): 0.50 min (method A)

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 6298-96-0.

Reference:
Patent; FLECK, Martin; NOSSE, Bernd; HEINE, Niklas; ROTH, Gerald Juergen; US2013/158004; (2013); A1;,
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These common heterocyclic compound, 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, 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: C5H13NO2

Preparation U N-[2-(2-Methoxyethoxy)ethyl]-1H-imidazole-1-carboxamide The title compound was prepared in 40% yield according to the procedure described in Preparation S above, using 2-(2-methoxyethoxy)ethylamine in place of 2-(4-morpholinyl)-1-ethanol.

The synthetic route of 2-(2-Methoxyethoxy)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bjorsne, Magnus; Ponten, Fritiof; Strandlund, Gert; Svensson, Peder; US2002/137766; (2002); A1;,
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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 36805-97-7 as follows. Product Details of 36805-97-7

Example 678-Amino-1 -methyl -4,5-dihydro-1 H-1 ,7,9-triaza-cyclopentafa1naphthalene-2,3- dicarboxylic acid 2-tert-butyl ester 3 -ethyl ester (N6) To a solution of i-methyl^-oxo^AthetaJ-tetrahydro-I H-indole^S-dicarboxylic acid 2-tert- butyl ester 3-ethyl ester XXVIA (4.67 mmol) in DMF (20 ml_), N,N-dimethylformamide di- tert-butyl acetal (2 mL) was added and the solution was stirred at 1000C overnight. After cooling to rt guanidine hydrochloride (14 mmol) and K2CO3 (14 mmol) were added and the mixture was heated at 1000C for 24 h. The organic solvent was evaporated to dryness. Chromatography on silica gel (AcOEt/hexane 1 :1 ) afforded the title compound (80% yield). ESI (+) MS: m/z 373 (MH+). 1H NMR: 1.28 (t, J=7.07, 3H), 1.55 (s, 9H), 2.68 (t, J=7.80, 2H), 2.79 (t, J=7.80, 2H), 4.18 (s, 3H), 4.23 (q, J =7.07, 2H), 6.40 (bs, 2H), 7.97 (s, 1 H).

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2008/65054; (2008); 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. 22483-09-6, name is 2,2-Dimethoxyethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 2,2-Dimethoxyethanamine

Preparation 22 [0100] [0101] A solution of aminoacetaldehyde dimethyl acetal (25 mL, 229 mmol) in toluene (120 mL) is treated at 0 C. with a 4.85 M sodium hydroxide solution (70.8 mL, 343.5 mmol). The mixture is stirred at 0 C. for 10 minutes and benzyl chloroformate (33.8 mL, 229 mmol) is added keeping the internal temperature below 20 C. during the addition. The mixture is warmed to room temperature over 4 hours. The organic layer is separated, washed with brine, dried over sodium sulfate, and concentrated to dryness to give the title compound (54 g, 98%). ES/MS (m/e): 240 (M+H).

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; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
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Synthetic Route of 37895-73-1, 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. 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 12 mL vial was charged with [Pd(cinnamyl)Cl]2(1,5 mol%), dppp (3 mol%). and a stirring bar. Then, 1,2-dibromo-benzene(0.5 mmol), DBU (4.0 eq) and toluene (3 mL) were injected by syringe underargon. The vial (or several vials) was placed in an alloy plate, which wastransferred into a 300 mL autoclave of the 4560 series from Parr Instrumentsunder argon atmosphere. After flushing the autoclave three times with CO, apressure of 10 bar of CO was adjusted at ambient temperature. Then, thereaction was performed for 16-24 h at 140 oC. After the reactioncompleted, the autoclave was cooled down with ice water to room temperature andthe pressure was released carefully. After evaporation of the organic solventthe residue was adsorbed on silica gel and the crude product was purified bycolumn chromatography using EA/pentane(1:1) for phthalimides and MeOH/EA (1:40) for the amides as eluent.

The chemical industry reduces the impact on the environment during synthesis 1,2-Dibromo-4,5-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Jianbin; Natte, Kishore; Wu, Xiao-Feng; Tetrahedron Letters; vol. 56; 2; (2015); p. 342 – 345;,
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Related Products of 101-55-3, These common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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 55-1 (16 g, 64 mmol) in TEA (160 mL) was added PPh3 (1.68 g, 6.4 mmol), cuprous iodide (0.6 g, 3.2 mmol), palladium acetate (0.72 g, 3.2 mmol) and trimethylchlorosilane (10.7 g, 96 mmol) and the reaction solution was stirred at 90 C. for 12 h, after which water (100 mL) was added and the resulting solution was extracted with EtOAc (100 mL×4). The organic phases were combined, dried over anhydrous Na2SO4, filtered and evaporated to give a crude product which was purified by column chromatography to afford the title compound 55-2 (yellow solid, 15 g, Yield 88%). 1H NMR (400 MHz, CDCl3): delta ppm 7.45 (d, J=8.78 Hz, 2H), 7.35-7.41 (m, 2H), 7.13-7.19 (m, 1H), 7.04 (d, J=7.78 Hz, 2H), 6.93 (d, J=8.78 Hz, 2H), 0.27 (s, 9H).

Statistics shows that 1-Bromo-4-phenoxybenzene is playing an increasingly important role. we look forward to future research findings about 101-55-3.

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
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