Month: March 2021

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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-6-methoxynaphthalene

Step 21.2: 6-methoxy-naphthalen-2-ylamine A solution of 2-bromo-6-methoxy-naphthalene (237 mg, 1 mmol), Pd (dba)2 mg, 0.05 mmol), tri-t-buthylphosphonium tetrafluoroborate (14 mg, 0.05 mmol), and lithium bis (trimethylsilyl)amide (1 M in hexane, 1.1 mL, 1.1 mmol) is stirred in toluene (2.5 mL) under argon for 6 h. The reaction mixture is taken in diethyl ether (20 mL), and quenched with 1 M HCI. The organic phase is extracted with water, the combined aqueous phases are treated with 1 M sodium hydroxide and extracted with DCM. The combined organic phases are dried over magnesium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (ethyl acetate) to afford 6-methoxy- naphthalen-2-ylamine (110 mg, 64 %), HPLC tR : 3.07, (M+H) + = 173.9.

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 5111-65-9.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H8FNO

Step C: 2,5-Difluoro-lambda/-{3-[(2-{[3-fluoro-4-(methyloxy)phenyl]amino}-4- pyrimidinyl)acetyl]phenyl}benzamide; To a solution containing 2.4 g (6.2 mmol) of lambda/-{3-[(2-chloro-4- pyrimidinyl)acetyl]phenyl}-2,5-difluorobenzamide and 60 mL of i-PrOH was added 0.92 g (6.5 mmol) of 3-fluoro-4-(methyloxy)phenyl amine and 0.1 mL of cone HCI. The reaction mixture was heated at 80 0C for 20 min, then diluted with an additional 60 mL of i-PrOH and heated at 90 0C for 13 h. The reaction mixture was allowed to cool to rt, then filtered. The filter cake was collected, slurried in DCM, and neutralized by the addition of aqueous NaHCO3. The organic layer was separated and the aqueous layer was further extracted with DCM. The combined organic layers were dried over MgSO4, filtered, and concentrated under recduced pressure. The residue was subjected to silica gel chromatography to give 1.76 g (59percent) of the title compound of Step C as a yellow solid: 1H-NMR (d6-DMSO, 400 MHz) delta 10.64 (s, 1 H), 9.83 (s, 1 H), 8.31 (d, 1 H1 J = 5.3 Hz), 8.25 (s, 1 H), 7.77 (d, 1 H1 J = 8.4 Hz), 7.65-7.69 (m, 1 H), 7.61 (d, 1 H1 J = 7.7 Hz), 7.53-7.59 (m, 1 H)1 7.42-7.47 (m, 4 H), 7.27 (d, 1 H, J = 9.2 Hz)1 7.13 (dd, 1 H1 J = 9.5 Hz and 9.5 Hz), 6.64 (d, 1 H, J = 5.3 Hz), 6.20 (s, 1), and 3.80 (s, 3 H), ; ESIMS: 561.07 (M+H+).

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 366-99-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/76140; (2009); A1;,
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Related Products of 1758-46-9, A common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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 2.45mmol of carboxylic acid derivatives (47) dissolved in 0.7mL of dry pyridine were added 0.1mL of phosphorous oxychloride. The mixture was led to?10¡ãC and then was added 39.2mmol of the appropriate amine or alcohol. The reaction was stirred at room temperature for 16h, then was added water and the product extracted with ethylacetate. The organic layer was washed with a NaHCO3 solution, dried and concentrated. The residue was purified by flash chromatography (Ethyl acetate 9: Light Petroleum 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:
Article; Federico, Stephanie; Margiotta, Enrico; Salmaso, Veronica; Pastorin, Giorgia; Kachler, Sonja; Klotz, Karl-Norbert; Moro, Stefano; Spalluto, Giampiero; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 837 – 851;,
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Related Products of 1163-19-5, 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 1163-19-5 as follows.

Using CdSe quantum dots as photocatalyst, take 10 mL of quantum dot stock solution, add appropriate amount of hydrochloric acid, centrifuge, discard the supernatant to retain solids, and redistribute the quantum dot solids to 4 mL of N,N-dimethylformamide (DMF). The concentration of the quantum dots was 2.47¡Á10-5 M; decabromodiphenyl ether (0.05 mmol) and triethylamine (2.5 mmol) were added to DMF, the rubber stopper was sealed, and the atmosphere was degassed for 20 min to remove the system. The oxygen in the room was irradiated for 24 hours at room temperature with an LED lamp (lambda > 460 nm). After the reaction, the yield and selectivity of diphenyl ether were determined by GC (FID) using diphenylacetonitrile as an internal standard. The debromination efficiency of decabromodiphenyl ether was determined by ion chromatography using sodium chloride as an internal standard. The experimental results show that decabromodiphenyl ether can be completely removed by quantum dot photocatalytic reduction and dehalogenation hydrogenation. The debromination efficiency is 65%, the yield of diphenyl ether is 54%, and the selectivity is as high as 83%.

According to the analysis of related databases, 1163-19-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Zhang Liping; Huang Maoyong; Wu Lizhu; Li Xubing; Xin Zhikun; (9 pag.)CN110204425; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 24988-36-1, name is 1,5-Dibromo-2,4-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 24988-36-1, Computed Properties of C8H8Br2O2

2,4-dibromo-1,5-dimethoxybenzene (88.8 g, 300 mmol), 2-fluorophenyl boric acid (100.7 g, 720 mmol), 2 M aqueous solution of Na2CO3 (600 mL), Pd[PPh3]4 (6.73 g, 6 mmol), DME (150 mL), and toluene (150 mL) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 36 hours. After the completion of the reaction, the obtained solution was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with toluene. The extract was dried with MgSO4, and was then filtered and concentrated. The resultant sample was purified by silica gel column chromatography. The purified product was concentrated to dryness, and was then recrystallized, whereby a white solid was obtained in an amount of 86.5 g in 88% yield. FD-MS analysis C20H16F2O2: theoretical value 326, observed value 326

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; Idemitsu Kosan Co., Ltd.; EP2301926; (2011); A1;,
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Reference of 36805-97-7, 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.

1 ,1-Di-tert-butoxy-W,A/-dimethylmethanamine (1.03 ml, 4.30 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1 -ethyl-1 H-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 39 (380 mg, 1.08 mmol) in toluene (10 ml). The reaction was heated at 80 C for 2 h then allowed to cool to RT. 1 ,1-Di-tert-butoxy-A/,/v- dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 80 C for 3 h then allowed to cool to RT. 1 ,1-Di-terf-butoxy-A/,W-dimethylmethanamine (1.03 ml, 4.30 mmol) was added then the reaction was heated at 110 C for 1 h then allowed to cool to RT. The reaction mixture was diluted with EtOAc (20 ml) then washed with water (2 x 20 ml), saturated aq. NaHC03 solution (2 x 20 ml) and brine (10 ml), then dried over Na2S04, filtered and evaporated to afford an orange solid (510 mg). The crude material was purified by flash column chromatography on a silica column (25 g). The column was eluted with EtOAc: heptane, increasing the gradient linearly from 0:100 to 50:50 over 10 column volumes. The desired fractions were combined and evaporated to yield the product as a white solid (320 mg, 72%).1H NMR (500 MHz, DMSO-de) delta 8.07 (s, 1 H), 7.98 (t, J = 5.8 Hz, 1 H), 7.77 (dd, J = 8.4, 1.3 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.41 – 7.12 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 5.9 Hz, 2H), 4.38 – 4.24 (m, 2H), 1.58 (s, 9H), 1.29 (t, J = 7.1 Hz, 3H). LC/MS (System A): m/z (ESI+) = 4 0 [MH+], R, = 1.17 min, UV purity = 99%.

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; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
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Reference of 105404-89-5, A common heterocyclic compound, 105404-89-5, name is 2,7-Dibromo-3,6-dimethoxynaphthalene, molecular formula is C12H10Br2O2, 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.

Into a 200-mL three-neck flask were put 3.0 g (8.7 mmol) of3,6-dibromo-2,7-dimethoxynaphthalene, 1.2 g (8.7 mmol) of 2-fluorophenylboronic acid, 2.4 g(17 mmol) of potassium carbonate, and 0.13 g (0.43 mmol) of tris(2-methylphenyl)phosphine.5 To this mixture was added 90 mL of toluene. The resulting mixture was degassed by beingstirred while the pressure was reduced. To the mixture was added 19 mg (87 IJ.mol) ofpalladium(II) acetate, and stirring was performed under a nitrogen stream at 110 oc for 7 hours.After the stirring, toluene was added to the mixture, and the resulting mixture wassuction-filtered through Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog10 No. 540-00135), Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No.531-16855), and alumina to give a filtrate. The filtrate was concentrated to give a solid. Thissolid was purified by silica gel column chromatography (as the developing solvent, first, tolueneand hexane in a ratio of 1:2 were used, and then toluene and hexane in a ratio of 1:1 were used)to give 1.1 g of a white solid which was an objective substance in a yield of 34 %. A synthesis15 scheme of Step 1 is shown below

The synthetic route of 105404-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; TAKEDA, Kyoko; OSAKA, Harue; SEO, Satoshi; SUZUKI, Tsunenori; HASHIMOTO, Naoaki; TAKITA, Yusuke; (225 pag.)WO2018/167612; (2018); A1;,
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Some common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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. name: 4-Bromo-2-methoxyaniline

a) tert-Butyl N-(4-bromo-2-methoxyphenyl)carbamate. A mixture of 4-bromo-2-methoxyaniline (34.0 g, 0.17 mol) and di-tert-butyl dicarbonate (44.5 g, 0.20 mol) in tetrahydrofuran (350 ml) was heated at reflux for 22 h. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (350 ml) and washed with 1 N citric acid (200 ml), dried over magnesium sulfate, filtered and evaporated to give tert-butyl N-(4-bromo-2-methoxyphenyl)carbamate as a yellow oil (80% pure, 57.10 g, 0.15 mol): 1H NMR (DMSO-d6, 400 MHz) delta 8.01 (s, 1H), 7.63 (d, 1H), 7.17 (d, 1H), 7.07 (dd, 1H), 3.82 (s, 3H), 1.45 (s, 9H); TLC (n-heptane/ethyl acetate=2:1) Rf 0.67.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59557-91-4, its application will become more common.

Reference:
Patent; CALDERWOOD, DAVID; ARNOLD, LEE; MAZDIYASNI, HORMOZ; HIRST, GAVIN C.; DENG, BOJUAN B.; JOHNSTON, DAVID N.; RAFFERTY, PAUL; TOMETZKI, GERALD B.; TWIGGER, HELEN L.; MUNSCHAUER, RAINER; US2003/187001; (2003); A1;,
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Reference of 19500-02-8, 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. 19500-02-8, name is 3-Methoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Part A Preparation of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. A solution of 44.4 g (344 mmol) of 3-methoxy-2-methylaniline and 75 g (344 mmol)of di-tert-butyl dicarbonate in 400 mL of THF was heated to maintain reflux for 4 hours. After concentrating at reduced pressure, the residue was taken up in ethyl acetate, washed with iN citric acid, water and dried (MgSO4). After removing the solvent at reduced pressure, the residue was crystallized from hexane to give 64.5 g (84percent yield) of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline, mp, 56-57¡ã C. Analysis for C13H19NO3: Calculated: C, 65.80; H, 8.07; N, 5.90 Found: C, 63.32; H, 7.83; N, 5.56.

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; Eli Lilly and Company; US6274578; (2001); B1;,
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Related Products of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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.

3,5-dimethoxyphenylacetylene 81 mg (0.50 mmol), silver nitrite 154 mg (1 mmol), N-bromosuccinimide 178 mg (1 mmol)10 mL of a pressure-tight sealed container was sequentially added, and 5 mL of 1,2-dichloroethane was further added.The mixture was stirred at room temperature, and the reaction was checked by TLC. The reaction was completed in 8 hours.The reaction solution was diluted with 10 mL of dichloromethane, and filtered to give a clear liquid.Separation by column chromatography (extraction of petroleum ether/ethyl acetate in a volume ratio of 100:1)The eluate containing the desired product were collected and the solvent was evaporated to give a white solid 3,5-dimethoxy-benzonitrile 42.4mg (52% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxyphenylacetylene, its application will become more common.

Reference:
Patent; Zhejiang University of Technology; Liu Yunkui; Zhang Jian; Bao Hanyang; (9 pag.)CN107641088; (2018); A;,
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