Month: October 2020

1535-73-5, 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 1535-73-5 as follows.

General procedure: Two mmol 5b1?5b20 was added to a dichloromethane solution containing 0.3 mL triethylamine at 0 ¡ãC. Then 1.2 equiv. 3-chloropropionyl chloride was dissolved in dry dichloromethane, and the obtained mixture was slowly added to the aniline solution at 0 ¡ãC. The reaction mixture was allowed to slowly warm up to room temperature, extracted with dichloromethane and finally washed with 2 M HCl. The organic phase was combined and dried with anhydrous MgSO4. Filtration and removal of the solvent under reduced pressure gave the crude product. The desired product was further purified by flash column chromatography with petroleum ether-EtOAc (20:1 to 10:1) to produce 6b1?6b20.

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

Reference:
Article; Zhu, Kongkai; Song, Jia-Li; Tao, Hong-Rui; Cheng, Zhi-Qiang; Jiang, Cheng-Shi; Zhang, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3693 – 3699;,
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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 126-38-5 as follows. 126-38-5

To a solution of 4-bromopyridin-2-amine (1.08 g, 6.24 mmol) in H20 (20 mL) were added l-bromo-2,2-dimethoxypropane (5.59 g, 30.5 mmol) and 4-methylbenzenesulfonic acid (209.4 mg, 1.216 mmol). The reaction mixture was heated to reflux and stirred for 12 hours and then adjusted to pH = 10 with saturated Na2C03 aqueous solution, the resulting mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc(v/v) = 3/1) to give the title compound as a yellow solid (750 mg, yield 57%).MS (ESI, pos. ion) m/z: 211.1 [M+H]+.

According to the analysis of related databases, 126-38-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
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366-99-4, 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.

To cyanuric chloride(0. 368 g, 2 mmol) inCH3CN atabout-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.39mL, 2.2 mmol) and stirred for about1 hour. The reaction mixture was then stirred at room temperature for about1 hour. Then cyclopropylamine (1.39 mL, 20 mmol) and DIEA (0.39 mL, 2.2 mmol) were added and the reaction mixture was stirred overnight at rt. The reaction mixture was worked up as usual, diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, concentrated under reduced pressure, and compound 157 was purified by silica gel column chromatography (200 mg,30percent), mp91-92 C ; HPLC : Inertsil ODS-3V C18, 40: 30: 30[KH2PO4(0. 01 M, pH3. 2):CH30H : CH3CN], 264nm, Rt 8.6 min, 99.1percent purity; MS(ESI) : m/z 331 (M+H, 100), 305 (0.8), 151 (. 3).

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; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2062-98-8

Put 0.51 g (4.2 mmol) of 4-ethylphenol into a three-necked flask, add 20 mL of dichloromethane, and add 1.99 g (6 mmol) of hexafluoropropylene oxide dimer (CF3CF2CF2OCF (CF3 ) COF, provided by Zhejiang Huanxin Fluorine Materials Co., Ltd., recorded as FEOCOF), after the addition, add 0.05mL (0.0007mmol) N, N-dimethylformamide (DMF), and slowly add 0.4mL ( 0.003 mmol) dry triethylamine,After the dropwise addition was completed, the reaction was stirred at 40 C. for 2 h.After the reaction, 20 mL of deionized water was added and extracted with dichloromethane (20 mL ¡Á 3). The organic phases were combined and dried over MgSO 4, filtered, and rotary evaporated to obtain a crude product. The crude product was separated by silica gel column chromatography (eluted with petroleum ether). Agent) to obtain a colorless slightly viscous liquid, that is, the target product, with a yield of 99.1%.

The synthetic route of 2062-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi Normal University; Yang Le; Chen Jiangang; Liu Zhaotie; Zhang Qiyu; Li Ruiqing; Shen Shukun; Liu Zhongwen; (11 pag.)CN110776426; (2020); A;,
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1579-40-4, The chemical industry reduces the impact on the environment during synthesis 1579-40-4, name is Di-p-tolyl Ether, I believe this compound will play a more active role in future production and life.

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

The chemical industry reduces the impact on the environment during synthesis Di-p-tolyl Ether. I believe this compound will play a more active role in future production and life.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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22236-08-4, 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 22236-08-4 as follows.

Reference Example 353-{[3-(Difluoromethoxy)phenyl]hydrazono}pentane-2,4-dione To a solution of 3-(difluoromethoxy)aniline (1000 mg, 6.25 mmol) in 10 mL of acetic acid and 2 mL of concentrated hydrochloride solution, sodium nitrite (518 mg, 7.50 mmol) in 4 mL of water was added dropwise at 0 C., and the mixture was stirred at 0 C. for 1 h. Then to the reaction mixture was added dropwise a solution of sodium acetate (1538 mg, 18.75 mmol) and acetylacetone (812 mg, 8.12 mmol) in 10 mL of ethanol and 6 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1:1) and hexane, and dried to give 3-{[3-(difluoromethoxy)phenyl]hydrazono}pentane-2,4-dione (1500 mg, 89%).LCMS: m/z=271 [M++H].

According to the analysis of related databases, 3-(Difluoromethoxy)aniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taniguchi, Takahiko; Kawada, Akira; Kondo, Mitsuyo; Quinn, John F.; Kunitomo, Jun; Yoshikawa, Masato; Fushimi, Makoto; US2010/197651; (2010); A1;,
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5473-01-8, Name is 2-Bromo-6-methoxyaniline, 5473-01-8, 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.

To a solution of 2-bromo-6-methoxyaniline (AK-90829) (1.000 mL, 7.55 mmol) in tetrahydrofuran (10 mL) was added Pd-PEPPSI-IPent-Cl (dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II), 0.208 g, 0.242 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.4 M in tetrahydrofuran solution of isopropylzinc(II) bromide (52 mL, 20.80 mmol) was added dropwise over 5 minutes, with nitrogen flushing through the system and the internal temperature rising slowly from 21¡ã C. to 32¡ã C. The reaction mixture was stirred for 15 hours at ambient temperature, at which point it was quenched with saturated aqueous ammonium chloride (50 mL), diluted with methyl tert-butyl ether (400 mL), and the layers were separated. The organic layer was filtered through a pad of silica gel and concentrated in vacuo. The crude material was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-40percent ethyl acetate/heptanes over 40 minutes to provide the title compound. 1H NMR (400 MHz, chloroform-d) delta ppm 6.89-6.66 (m, 3H), 3.87 (s, 3H), 3.86 (s, 2H), 2.96 (hept, J=6.8 Hz, 1H), 1.28 (d, J=6.9 Hz, 6H)+

Statistics shows that 2-Bromo-6-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 5473-01-8.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
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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. 6876-00-2 name is 1-Bromo-3-phenoxybenzene, 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. 6876-00-2

EXAMPLE 20 2-Fluoro-4-methyl-1-(3-phenoxyphenyl)-4-(4-trifluoromethoxyphenyl)pent-2-ene The method of Example 16 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.3 g), tetrahydrofuran (2 ml) and magnesium (22 mg), and 2-fluoro4-methyl-4-(4-trifluoromethoxyphenyl)pent-2-enyl acetate (Example 15) (0.1 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) to give the title compound (56 mg, 42%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-phenoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; British Technology Group, Ltd.; US5880162; (1999); A;,
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Adding a certain compound to certain chemical reactions, such as: 458-50-4, name is 4-Bromo-3-fluoroanisole, 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 458-50-4, 458-50-4

l-bromo-2-fluoro-4-methoxybenzene (750 mg, 3.658 mmol), potassium acetate (718 mg, 7.32 mmol), l,l’-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (300 mg, 0.367 mmol), bis(pinacolato)diboron (984 mg, 4.39 mmol) and 1,4-dioxane (10 ml) were sealed and subject to microwave irradiation at 140 ¡ãC for a total of 50 minutes (40 min + 10 min). LCMS of aliquot indicated complete consumption of starting material. The reaction crude was filtered through a pad of Celite (521). The filtrate was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated to afford a dark oil as the crude mixture of the title compound. To be used as it was for next step. LCMS (ESI) calc. = 252.13; found = 253.09 (M+l)+.

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, 4-Bromo-3-fluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
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60792-79-2, 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 60792-79-2 as follows.

In a typical run, sodium hydroxide (400 mg, 10 mmol) is dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) is added. The resulting reaction mixture is stirred at room temperature for 30 min. A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) is then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture is stirred at room temperature for 18 h. It is then concentrated under reduced pressure. The resulting residue is taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture is filtered and the filtrate is concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate.

According to the analysis of related databases, 2,2′-Oxybis(ethylamine) dihydrochloride, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; US2012/252810; (2012); A1;,
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