Month: June 2021

Application of 32338-02-6, A common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-methoxyaniline, molecular formula is C7H8BrNO, 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 mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 °C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

The synthetic route of 32338-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Reference of 588-96-5, 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. 588-96-5 name is p-Bromophenetole, 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.

Example I.1 (S)-N-(1-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide 147 mg (0.60 mmol) (S)-N-[1-(Piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) are added to a mixture of 100 mg (0.50 mmol) 1-bromo-4-ethoxy-benzene, 197 mg (2.00 mmol) sodium tert-butyrat, 59 mg (0.20 mmol) 2-(di-tert-butylphosphino)biphenyl and 46 mg (0.05 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 2.0 mL 1,4-dioxane. The mixture is stirred for 4 h at 45 C. After that time, the mixture is filtered over celite. The solvent is removed in vacuo from the filtrate. The residue is purified by HPLC (column: Waters XBridge 5 muM; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product. C23H30N2O2 (M=366.5 g/mol) ESI-MS: 367 [M+H]+

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/157425; (2012); A1;,
Ether – Wikipedia,
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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. 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H9FO2

A 3-neck 1-liter flask equipped with a low temperature thermometer, N2 line, and dropping funnel was charged with 1,4-dimethoxy-2-fluorobenzene (20.42 g, 131 mmol). The solid was dissolved in distilled THF (450 mL) and cooled to an internal temperature of -74 C. A 2.5 M solution of n-BuLi in hexane (63 mL, 157 mmol) was subsequently added over 25 min. under N2 via a dropping funnel. The reaction was maintained at -75 C. for 30 min., before adding solid sulfur (5.01 g, 157 mmol) in one portion. Nitrogen sparging of the reaction mixture was begun at this time and continued throughout the reaction. The internal temperature rose to -65 C. but quickly recorded to -75 C. The reaction temperature was maintained at -75 C. for 30 min. At this time, the excess dry ice in the dry ice/acetone bath was removed and the reaction was allowed to slowly warm to -20 C. over 1.5 h. The reaction was quenched with 2 N HCl with vigorous N2 bubbling until the color of the reaction turned pale yellow. The internal temperature of the reaction rose to 10 C. The reaction was extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The yellow residue was purified by silica gel chromatography with 20% EtOAc/hexane as the eluant to give the desired product as a light yellow solid. 1H 600 MHz NMR(CDCl3) ppm(delta): 3.84 (s, 3H), 3.86 (s, 3H), 6.56 (dd, J=1.8 Hz, J=8.9 Hz, 1H), 6.70 (t, 1H).

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; DiNinno, Frank P.; Hammond, Milton Lloyd; US2003/225132; (2003); 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., Safety of (Trimethoxymethyl)benzene

General procedure: To a solution of 2′-hydroxy-2-nitroacetophenone (13.3 g, 0.074 mol) in trimethyl orthoformate (66.4 mL) was added concentrated sulfuric acid (0.36 g). The reaction mixture was then refluxed for 6 h and distilled to a dry residue. The solid that formed was washed with water and recrystallized from methanol to give a brown solid in 84% yield (11.7 g).

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 707-07-3.

Reference:
Article; Iaroshenko, Viktor O.; Mkrtchyan, Satenik; Gevorgyan, Ashot; Vilches-Herrera, Marcelo; Sevenard, Dmitri V.; Villinger, Alexander; Ghochikyan, Tariel V.; Saghiyan, Ashot; Sosnovskikh, Vyacheslav Ya.; Langer, Peter; Tetrahedron; vol. 68; 11; (2012); p. 2532 – 2543;,
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Related Products of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: An autoclave was filled with catalyst (1 molpercent based on the molar amount of amine), flushed with argon and topped up with a solution of amine (0.1 mol) and orthocarboxylic acid ester (0.11-0.3mol) in 10 ml of methanol (or ethanol) and 0.5 ml of a 0.2 M solution of anhydrous ptoluenesulphonic acid in methanol (or ethanol). The mixture was heated to 120°C and hydrogen was injected to 40 bar and then the mixture was stirred at a constant pressure until hydrogen absorption could no longer be detected (0.2 – 6 h). After being filtered off from the catalyst, the filtrate was distilled.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EVONIK DEGUSSA GMBH; KADYROV, Renat; (19 pag.)WO2017/133913; (2017); A1;,
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Electric Literature of 6851-80-5,Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

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-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3,5-Dimethoxyphenylacetylene

Compound 3-iodo-1-((2- (trimethylsilyl) ethoxy) methyl) -1H-pyrazole 4-formamidine 2c (2.7 g, 7.3 mmol), 1-ethynyl-3,5-dimethoxybenzene (1.78 g, 11 mmol), triethylamine (2.2 g, 21.9 mmol), bis (triphenylphosphonium) palladium chloride (512 mg, 0.73 mmol) and anhydrous tetrahydrofuran (70 mL) were mixed, deoxygenated, and stirred at room temperature under an argon atmosphere for 15 hours.The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate / petroleum ether = 10/1 to 2/1) to give the target product 3-((3,5-dimethoxyphenyl) acetylene Yl) -1-((2- (trimethylsilyl) ethoxy) methyl) -1H-pyrazole-4-carboxamide 2d (1.5 g, yellow solid), yield: 51%.

According to the analysis of related databases, 171290-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H11BrO2

Example 7 (+-)-3-{1-[2-(2-Methoxyethoxy)ethyl]-trans-3,4-dimethylpiperidinyl}phenol To a solution of (+-)-3-(trans-3,4-dimethylpiperidinyl)phenol (60 mg, 0.29 mmol) in N,N-dimethylformamide (5.0 mL) at room temperature was added sodium hydrogencarbonate (27 mg, 0.32 mmol), and 1-bromo-2-(2-methoxyethoxy)ethane (59 mg, 0.32 mmol). The solution was heated at 120 C. for 1 hour, cooled and then water (10 mL) was added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude oil. This was purified by preparative HPLC on a Dynamax column, 42*250 mm; flow 8.0 mL min-1; employing U.V. detection at 275 nm; eluant gradient of acetonitrile:0.05 M aqueous ammonium acetate solution (90:10 to 10:90) to afford the title compound (71 mg, 80%) as its acetate salt. 1H-NMR (data for the acetate salt): 0.82 (d, 3H), 1.35 (s, 3H), 1.72 (m, 1H), 2.03-2.10 (m, 4H), 2.38 (m, 1H), 2.81-3.13 (m, 6H), 3.40 (s, 3H), 3.50-3.63 (m, 4H), 3.70-3.78 (m, 2H), 6.68 (m, 1H), 6.81-6.82 (m, 2H), 7.18 (t, 1H). MS (TSI+): m/z [MH+] 308.3; C18H29NO3+H requires 308.2.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6518282; (2003); B1;,
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Electric Literature of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

A) [3-(trifluoromethoxy)phenyl]hydrazine hydrochloride 3-(Trifluoromethoxy)aniline (3.68 ml) was dissolved in 6 M hydrochloric acid (71 ml), and an aqueous solution (4.7 ml) of sodium nitrite (2.08 g) was added dropwise over 20 min at -5° C. Tin (II) chloride (1.954 ml) was dissolved in 6 M hydrochloric acid (25 ml), and the solution was cooled to -5° C., and added quickly to the above-mentioned reaction mixture at -5° C. The mixture was stirred at -5° C. for 2 hr, and the precipitated solid was collected by filtration, washed with 0.1M hydrochloric acid, and dried under reduced pressure to give the title compound (2.72 g). 1H NMR (300 MHz, CDCl3) delta 6.81-7.03 (3H, m), 7.41 (1H, t, J=8.3 Hz), 8.64 (1H, br. s.), 10.35 (2H, br. s.)

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

Reference:
Patent; Yoshikawa, Masato; Suzuki, Shinkichi; Hasui, Tomoaki; Fushimi, Makoto; Kunitomo, Jun; Kamisaki, Haruhi; Taniguchi, Takahiko; US2013/150344; (2013); A1;,
Ether – Wikipedia,
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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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