Month: March 2021

These common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, 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. Recommanded Product: 64115-88-4

2.0 g of 1~bromo-2-(trifluoro-methoxy)benzene (8.3 mmol) were dissolved in 30 ml of dichloromethane. At 0-50C, 1.06 g of chlorosulfonic acid (9.13 mmol), dis? solved in 3 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature. Additional 5.5 equivalents of chloro? sulfonic in dichloromethane were added to drive the reaction to completion. Standard work-up was followed and silica gel chromatography with n-heptane- dichloromethane (6:4) as eluent gave 2.19 g of the title compound.1H-NMR (CDCI3, 400 MHz): delta [ppm] 8.3 (d, 1 H), 8.05 (dd, 1 H), 7.5 (dd, 1 H).

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

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2006/40180; (2006); A1;,
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Reference of 366-99-4,Some common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

Cyanuric chloride (11. 07g, 60 mmol) was dissolved in 40 mL CH3CN and was cooled toabout-20 C. To this was added DIEA (11.5mL, 60 mmol) followed by3-fluoro-4-methoxyaninline (8.47g, 60 mmol) in 20 mLCH3CN (reaction froze). The reaction was allowed to warm to room temperature after about1 hour at-20 C. TLC (2percent CH3OH/CH2Cl2) and mass spectroscopy indicated the presence of the compound 124. The reaction mixture was cooled to about 0 c before adding DIEA (11.5 mL, 66mmol).2-Aminomethyl-l-ethylpyrrolidine (7.77 g, 60 mmol) in CH3CN (10 mL) was added. The reaction was allowed to warm to rt and stirred overnight. Then DIEA (11.5 mL, 66 mmol) andS- (+)-2-methoxyethylpyrrolidine (6.91 g, 60 mmol) in 20mL 1,4-dioxane were added. The reaction was heated at about50 C overnight. The solvent was removed in vacuo, and the resulting residue was purified by flash chromatography on silica gel packed in ethyl acetate. The front running impurities were removed and subsequently the eluent was increased in polarity to 10percent CH30H: ethyl acetate. The material collected from the column was then dissolved in water and extracted inCH2C12 (4 times), dried overMgSO4, and concentrated to dryness to give a brown solid145 (9.7 g, 27.6percent yield),71-72 C ; HPLC: Inertsil ODS-3V C18, 40: 30: 30[KH2PO4 (O.O1M, pH 3.2) :CH30H : CH3CN], 264nm, Rt 5.37 min, 90.3 percent purity ; 1H NMR (600 MHz, CDC13,55 C) No. 7.69 (s, 1H), 7.08 (d, J= 7.8 Hz, 1H), 6.86 (t, J = 9 Hz, 1H), 4.29 (s, 1H), 3.90-3. 96 (m, 1H), 3.84 (s, 3H), 3.63-3. 81 (m,6H), 3.35 (s, 3H), 3.23-3. 25 (m, 1H), 2. 85(broad s, 1H), 2.78 (broad s 1H), 2.14 (broad s, 2H), 1.89-2. 04 (m, 6H), 1.37 (apparent t, J= 7.2 Hz, 3H) ; 13C NMR(150. 8 MHz, CDC13, 55 C)8 165. 8, 163.8 (2C), 152.3 (d,Jc-f= 243.5 Hz), 143.0 (142.9, rotamer or diastereumer), 133.7 (133.67, rotamer or diastereomer), 115.0, 114.4, 109.1 (108. 9, rotamer or diastereomer), 72.8, 66.6, 59.0,. 57. 0,56. 6,53. 7,51. 0,46. 8, 42.2, 28.4 (28. 2, rotamer or diastereomer), 23.1(23. 0, rotamer or diastereomer), 10.9 ; MS (ESI)inlz 460.2 (M+H, 44.7), 251.1 (47.7), 235.1 (27.5), 231.1 (37.4), 230.6 (100), 214.6 (36.5).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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Related Products of 910251-11-5, A common heterocyclic compound, 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, molecular formula is C2H5BF3KO, 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 pressure vial was charged with Intermediate 47 (350 mg, 0.969 mmol), potassium (methoxymethyl)trifluoroborate (295 mg, 1.94 mmol), RuPhos-Pd G2 (37.6 mg, 0.048 mmol) and cesium carbonate (947 mg, 2.91 mmol). The mixture was degassed (3x, vacuumlAr). Then dioxane (10 mL) and water (1.000 mL) were added, and the reaction mixture was degassed again. The pressure vial was capped, and the reactionmixture was stirred at 100 C for 18 h. Additional amounts of potassium (methoxymethyl)trifluoroborate (295 mg, 1.938 mmol), SPhos-Pd G2 (34.7 mg, 0.048 mmol), and cesium carbonate (947 mg, 2.91 mmol) were added. The reaction mixture was degassed (3x vacuumlAr), the pressure vial was capped, and the reaction mixture was stirred at 100 C for 18 h. Additional amount of SPhos-Pd G2 (34.7 mg, 0.048 mmol) wasadded, the reaction mixture was degassed, and was stirred at 125 C for 18 h. The reaction mixture was diluted with EtOAc, and CELITE was added. Solvent was removed under reduced pressure, and the residue was purified by flash chromatography (solid loading on CELITE) to give Intermediate 56A (61 mg, 19% yield) as an off-white solid. MS(ESI) m/z: 327.0 (M+H) ?H NMR (500MHz, DMSO-d6) oe ppm 8.44 (s, 1H), 8.09 (d, J=9.6Hz, 1H), 7.81 (d, J=9.6 Hz, 1H), 7.51 – 7.46 (m, 2H), 7.44 – 7.38 (m, 2H), 7.37 – 7.31 (m,1H), 5.28 (s, 2H), 4.94 (s, 2H), 3.83 (s, 3H), 3.32 (s, 3H).

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; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
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Synthetic Route of 645-36-3, 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 645-36-3 as follows.

2,2-diethoxyethan-1-amine 8 (3.63 g; 34.15 mmol) was dissolved in dry DCM (100 ml) and cooled to 0 C, then1,4-cyclohexanedione monoethylene acetal 7 (5.0 g; 31.05 mmol) was added dropwise. After10 min NaBH(OAc)3 (7.89 g; 37.26 mmol) was added in one portion and stirred for 2h atroom temp. The reaction mixture was diluted with DCM and saturated aq. NaHCO3 wasadded slowly, and then stirred for additional 15 min at rt. The layers were separated, theDCM layer was washed couple of times with saturated aq. NaHCO3, water, brine solutionand dried over anhydrous Na2SO4. After concentration the crude residue was filtered throughsilica column to afford pure compound 9a 7.2 g (85% yield).

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Annamalai, Murali; Hristeva, Stanimira; Bielska, Martyna; Ortega, Raquel; Kumar, Kamal; Molecules; vol. 22; 5; (2017);,
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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. 1535-73-5, name is 3-Trifluoromethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6F3NO

The title compound was prepared according to procedures similar to those described in Example 1 starting from 2-bromo-5-trifluoromethoxy-aniline, which was obtained as follows:A solution of 3-trifluoromethoxy-aniline (1.77 g) in toluene (20 ml) was treated with Lambda/-bromosuccinimide (1.87 g) at ambient temperature and the reaction mixture was stirred for 2 hours at ambient temperature, quenched by addition of water and the mixture extracted with ethyl acetate (3x 50 ml). The combined organic extracts were washed with aqueous sodium hydrogen carbonate (saturated), dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate 95:5) to afford 4-bromo-3-trifluoromethoxy-aniline (270 mg) and 2-bromo-5- trifluoromethoxy-aniline (1.45 g), which were both characterized by mass and NMR spectra. 4-bromo-3-trifluoromethoxy-aniline: MS (ES+) 256 / 258 (MH+); IH NMR (400 MHz, CDCl3) 3.5 (brs, 2H), 6.5 (d, IH), 6.7 (s, IH), 7.3 (d, IH). 2-bromo-5-trifluoromethoxy- aniline: MS (ES+) 256 / 258 (MH+); IH NMR (400 MHz, CDCl3) 4.2 (brs, 2H), 6.5 (d, IH), 6.6 (s, IH), 7.4 (d, IH).

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 1535-73-5.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CASSAYRE, Jerome Yves; PITTERNA, Thomas; CORSI, Camilla; MAIENFISCH, Peter; WO2011/3684; (2011); A1;,
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Related Products of 53087-13-1, A common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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.

Step-2: Synthesis of l-(benzyloxy)-3-(but-l-yn-l-yl)benzene sealed tubc/90 C/12 h To a stirred solution of l-(benzyloxy)-3-bromobenzene (2.5 g, 9.54 mmol) in 30 mL of MeOH:DMA:H20 (1: 1: 1) in a sealed tube, were added copper iodide (0.181 g, 0.95 mmol) and cesium carbonate (4.3 g, 13.3 mmol) at room temperature. This mixture was degassed with three vacuum/N2 cycles, and were added but-l-yn-l-yltrimethylsilane (2.4 g, 19 mmol, Example- 16, Step-2) followed by Pd(PPh3)2Cl2 (0.334 g, 0.479 mmol). The pressure tube was sealed and heated at 90 C for 12 h. Upon completion by TLC, the reaction mixture was diluted with water (250 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with water, brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography using 1% EtOAc in n-hexane to afford l-(benzyloxy)-3-(but-l-yn-l- yl)benzene (1.6 g, 72%).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (161 pag.)WO2016/196342; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2132-62-9, name is 1,2-Bis(4-methoxyphenyl)ethyne, 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 2132-62-9, HPLC of Formula: C16H14O2

In a clean quartz reactor, add acetophenone oxime (27.0 mg, 0.20 mmol), bis (4-methoxyphenyl) acetylene (57.1 mg, 0.24 mmol), and bis(2-methylallyl) (1,5-cyclooctadiene)ruthenium(II) (3.2 mg, 0.01 mmol), water (0.5 mL), polyethylene glycol 400 (0.5 mL), high-pressure mercury lamp as the photochemical reaction device of the light generating device Stir at room temperature for 24 hours. After the reaction was completed, saturated brine (10 mL) and ethyl acetate (5 mL ¡Á 3) were added for extraction. The ethyl acetate layer was collected, the solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate = 50/1, v / v) to obtain the target product 62.9 mg, a yellow solid in 89% yield .

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, 1,2-Bis(4-methoxyphenyl)ethyne, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan University; Hai Li; Wu Yong; Guan Mei; Lv Songyang; He Maoyao; Yang Zengbao; (8 pag.)CN111039867; (2020); 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. 1706-12-3, name is 1-Methyl-4-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-4-phenoxybenzene

A moderate stirrer was placed in a dry reaction tube (20 ml), palladium hydroxide/carbon (30 mol%), NaBH4 (1.5 equivalents) was added, and then the reaction tube was evacuated, filled with argon gas, and repeatedly replaced three times. A solution of 4-methyldiphenyl ether (0.2 mmol) and tetrahydropyrrole (0.7 mmol) dissolved in a solvent was slowly added to the reaction tube with a syringe under an argon atmosphere, and 10 uL was added to the reaction tube using a micro-injector. Water, then 1 mL of air was added to the reaction tube with a syringe, and the reaction tube was placed in an oil bath at 160 C to heat and stir the reaction. After 24 hours, the reaction was stopped, the reaction tube was taken out from the oil bath, cooled to room temperature, diluted with ethyl acetate, and then filtered over Celite, and the yield of benzene in the gas phase was 74%. The filtrate was concentrated and separated by an activated thin layer chromatography chromatography plate (eluent: n-hexane/ethyl acetate = 100/1).The final product was obtained in 5g and 4g. Product 5g (yield: 62%)

According to the analysis of related databases, 1706-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lanzhou University; Zeng Huiying; Cao Dawei; Li Chaojun; (19 pag.)CN109553592; (2019); A;,
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Synthetic Route of 175278-17-8, 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. 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 2-bromo-4-trifluoromethoxyaniline (0.500 g), cupper iodide (I) (18.6 mg), bis(triphenylphosphine)palladium (II) dichloride (68.5 mg), triethylamine (0.817 mL) and tetrahydrofuran (7.8 mL) was added phenylacetylene (0.279 mL) at room temperature under stirring, and the mixture was stirred at 80 C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with diethyl ether (30 mL) and then filtered through celite (registered trademark). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (206 mg).1H-NMR (CDCl3) delta ppm:4.32 (2H, br s), 6.70 (1H, d, J=8.8 Hz), 6.95-7.10 (1H, m), 7.20-7.30 (1H, m), 7.30-7.45 (3H, m), 7.45-7.60 (2H, m).

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

Reference:
Patent; KISSEI PHARMACEUTICAL CO., LTD.; US2012/129890; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, 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 104197-14-0, Formula: C7H5BrF2O

Example 27; Dicyclopropylmethyl [9-(3,5-difluoro-4-methoxyphenyl)-2,8-dimethyl-9H-purin-6-yl]-amine Dicyclopropylmethyl-^, 8-dimethyl-9H-purin-6-yl)-amine (0.05Og , 0.194 mmol), 4-bromo-2,6- difluoroanisole (0.087g , 0.388 mmol), Copper(l) Iodide (0.055g , 0.291 mmol), Cesium carbonate (0.158g , 0.485 mmol) and 1 ,10-Phenanthroline (0.070 g , 0.388 mmol) was dissolved in 2.0 ml of anhydrous DMF in a microwave vial with a septum cap. It was degassed alternatively with vacuum and nitrogen 3 times and then heated at 13O0C overnight in an oil bath. The crude was partitioned between 2 ml of water and 3 x 2 ml of DCM through a phase separating cartridge. Combined organics were dried under reduced pressure to yield a dark liquid which was purified by flash column chromatography in the ISCO system with 12g silica cartridge and a gradient of 0 to 40% EtOAc in heptane with sample loading in DCM. Fractions bearing product were combined to yield a transparent oil which was further purified by preparative HPLC method c. Fractions combined to yield the title compound as a solid (6.4mg, 8%).1H NMR (400MHz, CDCI3) delta = 0.39-0.60 (m, 8H), 1.07 (m, 2H), 2.47 (s, 3H), 3.52 (s, 3H), 4.90 (s, 3H),6.99 (d, 2H).LCMS (System 4): 2.90 mins m/z (APCI) = 401 [MH+], m/z (ES) = 401 [MH+]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroanisole, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; WO2009/144632; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem