Month: June 2021

171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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. category: ethers-buliding-blocks

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 × 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Formula 2 for the general method in accordance with, 1:1 t-BuOH/H2O (3 mL) in a compound 7c (80.8 mg, 300 mumol), 1-ethynyl -3,5-dimethoxybenzene (121 mg, 750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. Using ascorbate (60.0 mg, 300 mumol) was prepared in the desired compound. After stirring at room temperature for 5.5 hours the reaction mixture was purified by column chromatography (5: 1 hexane / EtOAc ? 20: 1 CH2Cl2 / MeOH) Compound 2c was obtained using as a brown solid (104mg, 80%).

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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Electric Literature of 22236-08-4, These common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)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.

General procedure: A round bottom flask was charged under argon with aniline 3(1.0 equiv.), aldehyde 4 (1.0 equiv.), and tetronic acid 5 (1.0 equiv.) in2-pentanol or ethanol [0.3 M]. Reaction was refluxed (at 125 C or 80 C respectively) for 1 h, then the solvent was evaporated undervacuum and the crude product purified by recrystallization inethanol or by flash chromatography on silica gel

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

Reference:
Article; Jeedimalla, Nagalakshmi; Flint, Madison; Smith, Lyndsay; Haces, Alberto; Minond, Dmitriy; Roche, Stephane P.; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 167 – 179;,
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These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, 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. category: ethers-buliding-blocks

To a stirred light brown solution of 10.0 g (49.6 mmol) 3-Fluoro-4-methoxy aniline in 56 ml DCM was added rapidly a solution of 4.38 g (52 mmol, 1.05 eq.) NaHCO3 in 70 ml of water. To the resulting biphasic mixture was added under vigorous stirring 5.72 ml (74.4 mmol, 1.5 eq.) methyl chloroformate over a period of 30 min. The light brown reaction mixture was stirred for 1.5h at RT. The organic phase was separated and washed twice with a total amount of 50 ml water, and the combined aqueous phases were washed twice with a total amount of 100 ml DCM. The combined organic phases were dried over 2 g Na2SO4 and filtered with suction on a funnel with a fritted disk. The cake was washed in total with 50 ml DCM. The DCM was partially removed under reduced pressure to about 1/3 of its original volume and then 70 ml heptane was added dropwise under stirring within 30 min, whereby the product precipitated. From this suspension, DCM was completely removed under reduced pressure. Finally, the suspension was stirred in an ice bath for 1h, the crystals were filtered off with suction on a funnel with a fritted disk and washed with three 10 ml portions, in total with 30 ml ice cold heptane. The wet off-white crystals were dried at 50°C in vacuo to yield 9.65 g (97.7percent of theory) of the title compound as off-white crystals (m.p. = 96.1-96.5°C) 1H-NMR data (CDCl3, 300 MHz): delta 7.29 (m, 1H), 6.98 (m, 1H,), 6.89 (dd, 1H), 6.44 (br s, 1H), 3.86 (s, 3H), 3.77 (s, 3H). MS m/e (percent): 200 ([M+H]+, 100).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. Hoffmann-La Roche AG; EP2011783; (2009); A1;,
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767-91-9, name is 2′-Methoxyphenyl acetylene, 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. COA of Formula: C9H8O

General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 mol%) and perfluorooctane sulfonateacid (2 mol%) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample.

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dong, Qizhi; Li, Ningbo; Qiu, Renhua; Wang, Jinying; Guo, Cancheng; Xu, Xinhua; Journal of Organometallic Chemistry; vol. 799-800; (2015); p. 122 – 127;,
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Adding a certain compound to certain chemical reactions, such as: 589-10-6, name is (2-Bromoethoxy)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 589-10-6, Computed Properties of C8H9BrO

(E)-ethyl 3-(l-(2-phenoxyethyl)-lH-pyrazol-4-yl)acrylateCesium carbonate (0.490g, 1.5 mmol) and l-(2-bromoethoxy)benzene (0.261 g, 1.30 mmol) were added to a solution of (E)-ethyl 3-( H-pyrazol-4-yl)acrylate (0.167 g, 1 mmol) in ACN (8 mL) at room temperature. The suspension was stirred overnight at 80C. The reaction mixture was then cooled down to room temperature and the precipitated solids were filtered off. The filtrate was concentrated and purified by silica gel column chromatography using a gradient of 0-60% of EtOAc in hexanes to provide the title compound (0.203g, 71%) as a colorless oil. ES+ (M+H)+ 287

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; REPLIGEN CORPORATION; JACQUES, Vincent; RUSCHE, James R.; PEET, Norton P.; SINGH, Jasbir; WO2012/118782; (2012); 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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of (Trimethoxymethyl)benzene

General procedure: To a stirred solution of the respective N-carbamate-protected aminovicinal diol 4 (0.50 mmol, 1 equiv) in CH2Cl2 (10 mL, 0.05 M) were added BF3·OEt2 (50 muL, 0.050 mmol, 0.1 equiv, 1.0 M solution in CH2Cl2) and trimethyl orthobenzoate (0.13 mL, 0.75 mmol, 1.5 equiv) at r.t. The resulting mixture was refluxed or stirred at r.t. under N2 until TLC showed complete conversion of the substrate. The reaction was quenched with sat. aq NaHCO3 and extracted with EtOAc (2 ×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane/EtOAc) to give the desired product 5.

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Park, Heemin; Kwon, Yongseok; Shin, Jae Eui; Kim, Woo-Jung; Hwang, Soonho; Lee, Seokwoo; Kim, Sanghee; Synthesis; vol. 49; 12; (2017); p. 2761 – 2767;,
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Electric Literature of 19500-02-8, The chemical industry reduces the impact on the environment during synthesis 19500-02-8, name is 3-Methoxy-2-methylaniline, I believe this compound will play a more active role in future production and life.

The imidate salt 2g2 (1.5g, 7.65mmol) was combined with 2-methyl-3-aminoanisole 2a2 (1.05g, 7.65mmol, 1 eq.) in ethanol (15 ml) under an N2atmosphere. The reaction mixture was stirred at R.T. (24 h) and monitored by HPLC.The reaction mixture was concentrated and then ether was added and the mixturefiltered. The solids were washed with ether and the combined ether washesconcentrated in vacuo. The resulting adduct 2m1 was purified by chromatography(SiO2, 15percent EtOAc/hexanes) to obtain as a yellow oil (2.11g, 99percent). MS electrospray:(M + H)+; 280 and (M – H)-; 278.

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-Methoxy-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, 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 37895-73-1, Formula: C8H8Br2O2

A 10 mL of a 1.6 M n-BuLi solution and 50 mL ofabsolute tetrahydrofuran were charged into a Schlenk flask (250 mL), the flask was cooled down to -20C,and a solution of 4.7 g (15.9 mmol) of 1,2-dibromo-5,6-dimethoxybenzene in 30 mL of absolute tetrahydrofuranwas added within half an hour ensuring thatthe temperature of the mixture did not exceed -20C.After stirring, a preliminarily prepared solution of3.53 g (16 mmol) of chlorodiphenylphosphine in20 mL of absolute tetrahydrofuran was added dropwisewithin an hour. Then the cooling was removed,and it was allowed to warm up to room temperature. A sample for GC-MS was collected (having preliminarytreated the mixture by a solution of sodium bicarbonate).The analysis showed the presence of 81% targetproduct of the total weight of the dry organic residuein the mixture. The solution was evaporated to dryness,and methanol was added to the residue. A viscousyellow precipitate was formed. The solvent wasevaporated, and diethyl ether was added. A fine whiteprecipitate was formed. The formed precipitate wasground, filtered off, and dried. Yield 3.82 g (60%). 1H NMR spectrum (300 MHz,CD2Cl2): delta (ppm) 7.42 (t, J = 3.5 Hz, 8H, Ar-H),7.08-7.03 (m, 12H, Ar-H), 6.82 (s, 2H, Ar-H), 3.18(s, 6H, OCH3). 31P{1H} spectrum (121.49 MHz,CDCl3): delta (ppm) -12.73 (s, PPh2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Dibromo-4,5-dimethoxybenzene, and friends who are interested can also refer to it.

Reference:
Article; Cheredilin; Sheloumov; Senin; Kozlova; Afanas?ev; Bespalova; Petroleum Chemistry; vol. 59; (2019); p. S72 – S87; Neftekhimiya;,
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Reference of 36865-41-5, These common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, 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 solution of [2], X=Br (1 wt, 1 mol eq.) in DMF (5 vol.) was added (0229) portionwise CS2CO3 (2.34 wt, 1.5 mol eq.) at room temperature, and then the reaction mixture was continued on stirring for 10 min. Then, l-bromo-3-methoxypropane (0.65 wt, 1.2 mol eq.) was added dropwise to the reaction mixture at room temperature and stirred for 16 h at the same temperature. The reaction was monitored by TLC. After completion of reaction, the resultant reaction mixture was diluted with water (3.2 vol.), and stirring was continued for 30 min to produce the solid, which was filtered, washed with water and dried under reduced pressure to obtain the product 5-bromo-2-chloro-3-(3-methoxypropoxy)pyridine [3], X=Br as off-white solid. 1H-NMR [300MHz, DMSO-d6]: d 8.10 (d, 1H, J= 1.5 Hz), 7.87 (d, 1H, J= 1.5 Hz), 4.15 (t, 2H, J= 6.0 Hz), 3.45(t, 2H, J= 6.4 Hz), 3.22 (s, 3H), 1.95 (quint, 2H, 7=6.4, 12.4 Hz).

Statistics shows that 1-Bromo-3-methoxypropane is playing an increasingly important role. we look forward to future research findings about 36865-41-5.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; CHEN, Shuai; DORSEY, Bruce D.; GOTCHEV, Dimitar B.; NGUYEN, Duyan; PALLERLA, Mahesh Kumar; PAMULAPATI, Ganapati Reddy; (76 pag.)WO2019/200109; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5, Safety of p-Bromophenetole

General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product.

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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ma, Hengchang; Bao, Zhikang; Han, Guobin; Yang, Ningning; Xu, Yufei; Yang, Zengming; Cao, Wei; Ma, Yuan; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 3; (2013); p. 578 – 584;,
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