Tag: M.W=100-200

Some common heterocyclic compound, 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, molecular formula is C10H10O2, 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: C10H10O2

General procedure: 1 ethynyl 2-methoxybenzene (2a) (265 mg, 2 mmol) and phenylazide (238 mg, 2 mmol) were added in 8 mL of a water and tertbutanol(1:1) mixture. Then 200 mL of freshly prepared 1 M aq.solution of sodium ascorbate (0.2 mmol) was added, following theaddition of 65 mL of aq. CuSO4*5H20 (5 mg, 0.02 mmol) solution. Thereaction mixture was stirred for approximately 14 h at room temperatureand reaction progress was monitored by TLC until its reactantswere completely consumed. Then 30 mL of ice cold waterwas poured into the reaction mixture and flask put in ice bath for15 min following the filtration to get white precipitate that werethoroughly rinsed with cold water (2 x 15 mL). The collected solidwas dried under vacuum to get pure product [23,24].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 126829-31-0, its application will become more common.

Reference:
Article; Jabeen, Sobia; Khera, Rasheed Ahmad; Iqbal, Javed; Asgher, Muhammad; Journal of Molecular Structure; vol. 1206; (2020);,
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Electric Literature of 454-90-0, The chemical industry reduces the impact on the environment during synthesis 454-90-0, name is 3-(Trifluoromethyl)anisole, I believe this compound will play a more active role in future production and life.

A flame-dried 100 mL Schlenk tube was charged with bis(pinacolato)diboron (350 mg, 1.38 mmol), [Ir(COD)Cl]z (12 mg, 0.018 mmol), sodium methoxide (5 mg, 0.09 mmol), and 4,4′-di-tert-butyl-2,2′-dipyridyl (8 mg, 0.03 mmol). The flask was evacuated, placed under argon, and 3-trifluoromethylanisole (2.5 mL) was added. The flask was restoppered and evacuated (full vacuum, 2 minutes). The flask was sealed under vacuum and maintained at 90 C. (oil bath) for 96 h. Thereafter, the contents were transferred to a round bottom flask with the aid of ethyl acetate and purified by Kugelrohr distillation. The product, a viscous oil, distills at 120 C. 10 p.m. Isolated yield 497 mg (1.65 mmol, 60%). 1H NMR (400 MHz, CDCl3) delta 7.62 (s, 1H); 7.43 (s, 1H); 7.18 (s, 1H); 3.82 (s, 1H); 1.32 (s, 1H).

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, 3-(Trifluoromethyl)anisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Regents of the University of California; Tanaka, Masahiro; Zhang, Chao; Shokat, Kevan M.; Burlingame, Alma L.; Hansen, Kirk; Bateman, Raynard L.; DiMagno, Stephen G.; (81 pag.)US2016/168151; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4344-55-2, name is 4-Butoxyaniline, 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 4344-55-2, name: 4-Butoxyaniline

Example 303-(4-Butoxyphenyl)-2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one; Ethyl 2-isothiocyanato-1H-pyrrol-3-carboxylate (400 mg) obtained by the method of Reference Example 36, or a method pursuant to thereto, and 4-butoxyaniline (330 mg) obtained by the method of Reference Example 12, or a method pursuant to thereto, were added to acetonitrile (5 ml). The resulting mixture was stirred for 4 hours at 70 C., and then was concentrated under reduced pressure, to obtain a crude solid. This crude solid was added to a solution of potassium tert-butoxide (440 mg) in ethanol (5 ml), and the resulting mixture was stirred for 24 hours at room temperature. Subsequently, 1 M hydrochloric acid was added thereto until the pH value reached 6. A solid precipitated therefrom was collected by filtration, washed with water and petroleum ether, and then dried under reduced pressure, and thus the title compound (254 mg) was obtained.MS(ESI+):316(M+H).

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

Reference:
Patent; Suzuki, Hideo; Fujimoto, Takuya; Yamamoto, Takeshi; US2010/190747; (2010); 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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

General procedure: In an oven-dried Schlenk tube 2-iodophenol 6 (0.5 mmol), terminalalkyne 4 (0.5 mmol), PdO/MWCNT (5 mol%), K2CO3(1 mmol) and solvent (DMSO) (1.0 mL) were added. Theresulting reaction mixture was stirred at 120 C for 24 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was allowed to coolto room temperature, then diluted with (10 mL) ethyl acetateand NH4Cl (10 mL) was added fallowed by extraction withethyl acetate. The organic layers were dried (Na2SO4) andconcentrated in vacuum. Purification of the residue by silicagel column chromatography using petroleum ether/ethylacetate as the eluent furnished the benzofuran 7.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lakshminarayana, Bhairi; Mahendar, Lodi; Chakraborty, Jhonti; Satyanarayana, Gedu; Subrahmanyam, Ch; Journal of Chemical Sciences; vol. 130; 5; (2018);,
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Synthetic Route of 20781-20-8, 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 20781-20-8 as follows.

To a solution of ethyl (4aS)-l-(4-fluorophenyl)-6-oxo-4,5,7,8-tetrahydrobenzo[f]indazole-4a- carboxylate (lg) (3.16 g, 8.92 mmol) and (2,4-dimethoxyphenyl)methanamine (2.68 mL, 17.8 mmol) in DCE (40 mL) was added acetic acid (1.54 mL, 26.8 mmol). After the reaction was stirred at rt for 5 min and cooled down in an ice-bath, sodium triacetoxyborohydride (5.l0g, 24.1 mmol) was added in portions. 5 Minute later, the reaction solution was allowed to warm to rt and continued stirring for 30 min. The solution was quenched (sat. aq. NaHCCE) and extracted (EtOAc). The organic layers were washed (brine), dried (Na2SC>4) and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (0%-75% EtO Ac/hexanes, a gradient elution) to provide the title compound (4a) (4.15 g, 92% yield) as an off-white solid m/z (ESI, +ve ion) = 506.3 [M+H]+

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; REW, Yosup; SUN, Daqing; YE, Qiuping; ZHOU, Haiying; KAWAI, Hiroyuki; MOORE, Jared; PHAM, Johnny; WU, Kejia; ZHU, Liusheng; (116 pag.)WO2020/76999; (2020); A1;,
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Related Products of 4342-46-5, These common heterocyclic compound, 4342-46-5, name is 4-Methoxycyclohexanamine, 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: To a solution of 7a-d (1.0 equiv.) and amine (2.0 equiv.) in dioxane was added glacial acetic acid (0.2 equiv.), then the mixture was stirred and heated at 110 C in a sealed tube for 10-20 h. The mixture was concentrated under vacuum, and the residue was purified by column chromatography on silica gel, using petroleum ether/ethyl acetate to afford target products 8-25.

The synthetic route of 4342-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Dongfeng; Liu, Yang; Zhang, Chunlin; Zhang, Hao; Wang, Bin; Xu, Jian; Fu, Lei; Yin, Dali; Cooper, Christopher B.; Ma, Zhenkun; Lu, Yu; Huang, Haihong; Molecules; vol. 19; 4; (2014); p. 4380 – 4394;,
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Application of 578-57-4, These common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, 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 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 × 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.

Statistics shows that 1-Bromo-2-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 578-57-4.

Reference:
Article; Yi, Zhou; Huang, Manna; Wan, Yiqian; Zhu, Xinhai; Synthesis; vol. 50; 19; (2018); p. 3911 – 3920;,
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Reference of 1535-73-5, These common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 solution of corresponding aniline (9.32mmol) and diethyl ethoxymethylenemalonate (9.32mmol) in ethanol (20mL) was heated at 90C for 18h. After the solvent was removed under reduced pressure, the residue was extracted with ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by open column chromatography (eluent: n-hexane/ethyl acetate=4 : 1) to give corresponding compound 16-27.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mori, Shuichi; Iinuma, Hiroto; Manaka, Noriaki; Ishigami-Yuasa, Mari; Murayama, Takashi; Nishijima, Yoshiaki; Sakurai, Akiko; Arai, Ryota; Kurebayashi, Nagomi; Sakurai, Takashi; Kagechika, Hiroyuki; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 837 – 848;,
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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. 34967-24-3, name is 3,5-Dimethoxybenzyl amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H13NO2

General procedure: Synthesis of (2R, 3R, 4S, 5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl) tetrahydrofuran-3,4-diol, 2. In a 7 mL MW vessel, 6-chloropurinoriboside 3 (20 mg, 0.07 mmol), benzylamine 4 (7.5 mg,0.07 mmol, 7.7 muL) and triethylamine (7.08 mg, 0.07 mmol, 9.8 muL)were mixed. The solid mixture was stirred in CEM Explorer. MWMethod: T = 210 C, Power: 300 W, Hold Time: 1 min, P = 250 PSI,Power Max activated. After cooling, the solvent was removed in vacuoand the crude was dissolved in methanol and then purified on PTLC(DCM/MeOH 9:1) to afford compound 2 as white solid (24 mg, 94%).C17H20N5O4: 358.1510; Found 358.1515. Rt: 8.92 min.

According to the analysis of related databases, 34967-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abate, Mario; Bifulco, Maurizio; Buonocore, Michela; Ciaglia, Elena; Covelli, Verdiana; D’Ursi, Anna Maria; Gazzerro, Patrizia; Grimaldi, Manuela; Randino, Rosario; Rodriquez, Manuela; Scrima, Mario; Stillitano, Ilaria; Tosco, Alessandra; Bioorganic Chemistry; (2020);,
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22236-08-4, name is 3-(Difluoromethoxy)aniline, 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. SDS of cas: 22236-08-4

General procedure: The synthesis was carried out by using the synthetic method a. To a solution of 2-picolinic acid (0.871 g,7.08 mmol), N-hydroxybenzotriazolehydrate (HOBt.H2O,1.084 g, 7.08 mmol), diisopropylethylamine(DIPEA, 1.83 g, 14.17mmol) and N-(3-methylaminopropyl)-N?-ethylcarbodiimidehydrochloride (EDCHCl, 2.036 g, 10.63mmol) in anhydrous 1,4-dioxane (60 mL) was added 3-fluoro-3-methoxyanilline (1.00 g, 7.08 mmol) at room temperature. The mixture was heated to 50 oC and stirred overnight. To the reaction mixture was added 300 mL of dichloromethane, and sequentially washed with water (3 x100 mL). After the organic layer was separated and concentrated, the reaction mixture was purified by silica-gel chromatography (hexane/ethyl acetate) to give the product as a pale-yellow solid (1.559 g, 6.33mmol, 89.4% yield).

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Zhaoda; Kil, Kun-Eek; Poutiainen, Pekka; Choi, Ji-Kyung; Kang, Hye-Jin; Huang, Xi-Ping; Roth, Bryan L.; Brownell, Anna-Liisa; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 3956 – 3960;,
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