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. 4863-91-6, name is 3-Chloro-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

A mixture of Example A47 (200 mg, 0.363 mmol), DIEA (188 mg, 1.452 mmol) and 3-chloro-5-fluoroaniline (211 mg, 1.452 mmol) in dioxane (5 mL) was heated at 80 C. overnight. The mixture was cooled to RT, treated with EtOAc and satd. NaHCO3 and the resulting solid collected via filtration and dried to afford crude 1-(4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-chloro-5-fluorophenyl)urea (91 mg, 39% yield) which was carried on to the next step without further purification. MS (ESI) m/z: 638.2 [M+H]+.

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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. Recommanded Product: 220227-21-4

A solution of ferf-butyl thiazol-4-ylcarbamate (3.46 g, 17.3 mmol) in tetrahydrofuran (150 mL) at -78 C was treated with lithium 6/’s(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 20.8 mL, 20.8 mmol). The resulting mixture was stirred at -78 C for 0.5 h, allowed to warm to ambient temperature and stirred for a further 0.5 h. The reaction mixture was cooled to -78 C and treated with a solution of 2,4,5- trifluorobenzene-1-sulfonyl chloride (3.99 g, 17.3 mmol) in tetrahydrofuran (30 mL). The resulting mixture was stirred at -78 C for 4 h, allowed to warm to ambient temperature and stirred for a further 16 h. The reaction mixture was diluted with ethyl acetate (300 mL) and washed with saturated aqueous ammonium chloride (2 x 150 mL) and brine (2 x 150 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a gradient of ethyl acetate in hexanes to afford terf-butyl thiazol-4-yl((2,4,5- trifluorophenyl)sulfonyl)carbamate as a beige solid in 62% yield (4.23 g): 1H NMR (300 MHz, CDCI3) 6 8.79-8.75 (m, 1 H), 8.06-7.96 (m, 1 H), 7.53-7.48 (m, 1H), 7.15-7.04 (m, 1 H), 1.34 (s, 9H); MS (ES+) m/z 394.7 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 220227-21-4, its application will become more common.

Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); 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. 146447-18-9, name is 5-Bromo-2-chloro-4-fluoroanisole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5BrClFO

1.0 g (4.2 mmol) of 5-Bromo-2-chloro-4-fluoroanisole, 47 mg (0.21 mmol) of palladium acetate, 180 mg (0.29 mmol) of binap, 0.65 g (6.7 mmol) of sodium tert-butoxide, and 3.6 g (42 mmol) of piperazine in 3 mL of dry toluene werw heated at 110 C. for 24 hours. The reaction was partitioned between ethyl acetate and water, and the phases were separated. The ethyl acetate phase was washed once each with water and brine, and was concnentrated. The residue was purified by chromatography to give 1-(4-Chloro-2-fluoro-5-methoxy-phenyl)-piperazine.

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 146447-18-9.

Reference:
Patent; ChemoCentryx, Inc.; US2004/162282; (2004); A1;,
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Application of 14752-66-0,Some common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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 the sodium arylsulfinate (1 mmol), Cu(OAc)2 (0.5 mmol)and CH3CN (1 mL) was stirred at 60 C in air for 3 h. After this, themixture was cooled to room temperature and filtered through a filterpaper. The organic phases were evaporated under reduced pressure andthe residue was subjected to flash column chromatography (silica gel,ethyl acetate/petroleum ether = 1/10) to obtain the desired product.All products are known compounds and were characterised by 1HNMR, 13C NMR and HRMS.

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Peng, Yao; Journal of Chemical Research; vol. 38; 5; (2014); p. 265 – 268;,
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Synthetic Route of 53531-69-4, 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. 53531-69-4, name is (4-Bromophenyl)methanesulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Various alkyl halides 23a-k (2.5 mmol) and thiourea (0.19 g, 2.5 mmol) were refluxed together in EtOH (2.5 mL) for 1 h. Afterr emoval of EtOH at reduced pressure, the obtained solid was slowly added to a mixture of NCS (1.33 g, 10 mmol), 2 M HCl (0.68 mL) and MeCN (4 mL) over 15 min. Upon completion of the reaction (TLC monitoring), the solvent was removed under vacuum. Then H2O(5 mL)was added to the residue and stirred for 15 min, the resulting solid was filtered and dried under an infrared lamp to afford the corresponding sulfonyl chlorides 24a-k. Without further purification, 24a-k was added in portions to a solution of NaN3 (195 mg ,3 mmol) in acetone/H2O (10 mL, acetone/H2O = 1:1) at 0 C. After being stirred at room temperature for 4 h, the reaction mixtur ewas concentrated in vacuo and H2O (10 mL) was added to the residue. The aqueous solution was extracted with CHCl3 (3 x 10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford sulfonyl azides 25a-k.

The synthetic route of (4-Bromophenyl)methanesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fang, Sen-Biao; Li, Hui-Jing; Nan, Xiang; Wu, Rui; Wu, Yan-Chao; Zhang, Jing; Zhang, Zhi-Zhou; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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Synthetic Route of 2687-12-9, These common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, 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.

A flame dried 100 mL round-bottomed flask under Ar was charged with chlorotrioctylstannane (2.0 g mL, 4.05 mmol), cinnamyl chloride (0.8 g, 5.3 mmol),magnesium powder (0.14 g, 5.7 mmol), a crystal of iodine and dry THF (50 mL). The resulting mixture was sonicated at 50 C for 6 h and was then stirred overnight at room temperature. Water (50 mL) was added and the mixture was transferred to a separating funnel. The water layer was separated and the remaining organic layer was diluted with heptane (100 mL), washed with acetonitrile (2 x 50 mL), water (50 mL) and finally againwith acetonitrile (3 x 50 mL). Drying on MgSO4, filtration and concentration in vacuo afforded a crude product, which was purified by column chromatography on silica gel using petroleum ether as the eluent, providing trioctyl(3-phenylallyl)stannane (1.42 g, 2.5 mmol, 62 %) as a faint yellow oil. ?H-NMR (CDC13, 400 MHz) & 7.40-7.26 (m, 2H), 7.25-7.20 (m, 2H), 7.12-7.06 (m, 1H),6.39 (dt, 1H, I = 15.5, 8.8 Hz), 6.17 (dt, 1H, I = 15.5, 1.0 Hz), 2.04-1.84 (m, 2H), 1.68-1.40 (m, 6H), 1.36-1.16 (m, 30H), 0.98-0.82 (m, 15 H); ?3C-NMR (100 MHz, CDC13):138.9, 131.3, 128.5, 125.8, 125.3, 125.1, 34.5, 32.0, 29.4, 29.3, 27.0, 22.8, 16.3, 14.2, 10.0;?9Sn-NMR (149.2 MHz, CDC13) & -12.8.

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; KUVSHINOV, Alexandr; FRANCK, Philippe; DEPRAETERE, Stefaan; MAES, Bert; DE HOUWER, Johan; WYBON, Clarence; STERCKX, Hans; SERGUEEV, Serguei; WO2013/167585; (2013); A2;,
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These common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, 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. SDS of cas: 108-41-8

General procedure: Under N2 atmosphere, KOtBu (1.0 mmol), NHC-Pd(II)-Im 2a (1.0 mol %), dry dioxane (1.0 mL), morpholine 3 (0.8 mmol), and aryl chloride 4 (0.7 mmol) were successively added into a Schlenk reaction tube. The mixture was stirred at 70 C for 3 h. The solvent was removed under reduced pressure and the residue was purified by a flash chromatograph on silica gel to give the pure products 5.

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Lei; Gao, Ting-Ting; Shao, Li-Xiong; Tetrahedron; vol. 67; 29; (2011); p. 5150 – 5155;,
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Synthetic Route of 112-26-5, A common heterocyclic compound, 112-26-5, name is 1,2-Bis(2-chloroethoxy)ethane, molecular formula is C6H12Cl2O2, 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.

A mixture of 3.2 g (10.1 mmol) of sodium 2-(diphenylphosphoryl) phenolate [10] and 0.93 g (5.0 mmol) of 1,8-dichloro-3,6-dioxaoctane in 7 mL of anhydrous dioxane was placed into the laboratory system with focused microwave heating in hermetically closed glass vial. The mixture was heated at 150C (50 W) for 0.6 h. After cooling, the reaction mixture was poured into 50 mL of water, acidified with conc. HCl to pH 1, and extracted with CHCl3 (3 ¡Á 30 mL). The extract was washed with dilute HCl (2 ¡Á 30 mL), and water (3 ¡Á 35 mL), and evaporated ina vacuum. To the residue 20 mL of diethyl ether was added, and the precipitate was filtered off. The filtrate was chromatographed.

The synthetic route of 112-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baulin; Ivanova; Polyakova; Pyatova; Krivorot’ko; Tsivadze; Russian Journal of General Chemistry; vol. 85; 4; (2015); p. 899 – 905; Zh. Obshch. Khim.; vol. 85; 4; (2015); p. 899 – 905,7;,
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Electric Literature of 13078-79-0, 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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under nitrogen atmosphere, ethanol (30 mL), immediate III (3 mmol) and titanium (IV) isopropoxide (9 mmol) were added to a three-necked round bottom flask and stirred for 0.5 h, then the substituted ethylamine (3 mmol) was dropped into the solution and stirred for 3 h at room temperature. Subsequently, sodium borohydride (4.5 mmol) was added to the flask slowly, the reductive amination reaction was maintained for 3 h. According to the TLC monitoring results, the ammonia water (2 mol L-1, 10 mL) was poured into the flask to quench the reaction. The resulting mixture was filtered in vacuum and evaporated on rota vapor (Buchi). Hereafter, dissolved the residue with ethyl acetate (50 mL), and the solution was washed with 2 mol L-1 hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively, dried over anhydrous Na2SO4 and filtered. Solvent was evaporated in vacuum, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate as eluents). Finally, the samples were recrystallized from ethyl acetate / petroleum ether to afford target compounds with higher purity.

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, 2-(3-Chlorophenyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cai, Nan; He, Lu; Wang, Kai; Feng, Zhihui; Cui, Zining; Ji, Mingshan; Qi, Zhiqiu; Qin, Peiwen; Li, Xinghai; Bioorganic and Medicinal Chemistry Letters; vol. 30; 4; (2020);,
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Synthetic Route of 461432-23-5, 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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 1.6 M n-BuLi in hexanes (0.1 mL, 0.158 mmol) was added dropwise at -78 C to a stirred solution of compound 15 (50 mg, 0.158 mmol) in dry THF (2.5 mL) and the mixture was stirred at this temperature for 45 min. Then, a solution of amide 22 (100 mg, 0.158 mmol, 1 eqiv.) in THF (1 mL) was added dropwise to this mixture at the same temperature, the resulting mixture was stirred at this temperature for another 1 h, and then left at ambient temperature for 2 days. Then, the mixture was cooled in an ice bath, a saturated aqueous solution of NH4Cl (3 mL) was added and the mixture was extracted with DCM (3 * 5 mL). The combined organic layers were dried over Na2SO4, the solvent was removed under reduced pressure and the residue was chromatographed on a silica gel column (hexane/ethyl acetate 10:1) to give product 2 (45 mg, 35%) as a colorless oil.

The synthetic route of 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Triantakonstanti, Virginia V.; Mountanea, Olga G.; Papoulidou, Kyriaki-Eleni C.; Andreou, Thanos; Koftis, Theocharis V.; Gallos, John K.; Tetrahedron; vol. 74; 39; (2018); p. 5700 – 5708;,
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