Month: July 2021

Synthetic Route of 29578-39-0, 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 29578-39-0 as follows.

A mixture of 1-bromo-3-fluoro-5-methoxy-benzene (80 g, 0.39 mol), TEA (118 g, 1.17 mol), Pd(OAc)2 (16 g, 20%) and DPPP (16 g, 20%) in MeOH (800 mL) is stirred under a 3 Mpa atmosphere of CO for 2 days. The mixture is filtered and the filtrate is concentrated under reduced pressure. The crude is purified by flash silica gel chromatography to afford compound D-9-1 (42 g, 59% yield).

According to the analysis of related databases, 29578-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; BRENNEMAN, Jehrod Burnett; GINN, John David; HOPKINS, Tamara Denise; LOWE, MIchael D.; SARKO, Christopher Ronald; WESTBROOK, John A.; YU, Maolin; ZHANG, Zhonghua; (233 pag.)US2016/24059; (2016); A1;,
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Related Products of 4393-09-3, 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. 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a typical reaction, the Wang resin (3, 2.0 g, 1.2 mmol/g, 100-200 mesh and 1% DVB) was swollen in CH2Cl2 (20 mL). 5-Bromopentanoic acid (4, 2.15 g, 12.0 mmol) and DIC (1.51 g, 12.0 mmol) were dissolved in the minimum volume of CH2Cl2/DMF (1:1) required for complete dissolution. The activated scaffold solution was added to the resin, followed by the addition of slurry of DMAP (4 mg, 10 mol %) in CH2Cl2 (0.5 mL). The reaction vessel was shaken at room temperature for 48 h. The resin was washed with CH2Cl2 (2 × 25 mL), DMF (2 × 25 mL), MeOH (2 × 25 mL) again followed by DMF (2 × 25 mL), CH2Cl2 (3 × 25 mL), and then further dried in vacuo overnight to afford the resin-bound 5-bromopentanoic acid in good yield (2.73 g, 81%). Next, to the resin-bound 5-bromopentanoic acid (2.70 g, 3.9 mmol), swelled in DMF (10 mL), K2CO3 (2.13 g, 15.6 mmol) was added at ambient temperature, and the reaction suspension was stirred for another 30 min. Later, methyl 2-azido-4-hydroxy-5-methoxybenzoate (5, 1.73 g, 7.8 mmol) was added to the resin. The reaction suspension was stirred at 50 C for 48 h. The solid-support was washed with water (3 × 20 mL), CH2Cl2 (2 × 20 mL), MeOH (3 × 15 mL), and then dried in vacuo to afford the resin-bound precursor 6a (3.07 g, 75%). To a suspension of this resin-bound ester in 1,4-dioxane (10 mL) was added 1 N NaOH solution (2.5 mL) and the reaction mixture was heated at 80 C for 12 h. On cooling, the resin was filtered and rinsed with water (2 × 15 mL), water/dioxane (1:9, 2 × 15 mL), MeOH (2 × 15 mL), CH2Cl2 (2 × 15 mL), Et2O (2 × 15 mL) and dried in vacuo to afford the resin-bound acid. Next, to the resin-bound 2-azido-4-(5-ethoxy-5-oxopentyloxy)-benzoic acid (2.81 g, 2.6 mmol) swelled in CH2Cl2 (10 mL), EDCI (0.99 g, 5.2 mmol), HOBt (0.71 g, 5.2 mmol) and l-proline methyl ester (7a, 0.84 g, 6.5 mmol) were added. This reaction mixture was stirred for 12 h at room temperature, then resin was filtered and washed with H2O (3 × 10 mL), CH2Cl2 (2 × 10 mL), MeOH (3 × 10 mL) and Et2O (3 × 10 mL) to afford the resin bound methyl 5-(5-azido-4-(2-formylpyrrolidine-1-carbonyl)-2-methoxyphenoxy) pentanoate 8a in good yield (2.89 g, 71%). To a suspension of this resin (0.110 g, 1.2 mmol) in CH2Cl2 (5 mL), AlCl3 (0.79 g, 6 mmol), NaI (0.22 g, 2 mmol) and 2-(4-methoxyphenyl)ethanamine (9a, 0.35 mL, 2.4 mmol) were added at room temperature and stirred for 6 h. Aqueous 1 M potassium carbonate solution (2 mL) was added to the reaction mixture followed by excess of NaI, quenched with saturated sodium thiosulfate (Na2S2O3), and then resin was separated by simple filtration and washed with CH2Cl2 (10 mL). The removal of excess amine impurities from the final resin cleaved crude product was achieved by solid-supported liquid-liquid extraction (SLE) with a fritted vessel previously packed with ?Varian?s Hydromatrix?. The crude compound 1a which contains excess of amine was passed through the Hydromatrix support into a collection plate below, while the amine salts were retained by the solid matrix, resulting in the effective removal of the amine impurities. This filtrate and washings were evaporated to dryness under reduced pressure. Finally, it was further purified by the preparative thin layer chromatography by using ethyl acetate:methanol (98:2) as eluent to afford the corresponding compound 1a in high purity (brown solid, 0.013 g, 56%).

The synthetic route of (2,3-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Prabhakar; Shankaraiah, Nagula; Markandeya, Nagula; Venkat Reddy; Srinivasulu, Vunnam; Sathish, Manda; Tetrahedron Letters; vol. 54; 33; (2013); p. 4435 – 4441;,
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Some common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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. category: ethers-buliding-blocks

To the reaction vessel of 3000 L was added the above-obtained 2,3-difluoro-5-bromoanisole and 215 kg of AlCl3,And then pumped into 1800L of toluene,Sealed reactor, heated to reflux after 5h sampling analysis,Raw materials have been basically complete.The material with nitrogen into the 5000L washing kettle,Pumped into 1000L water stirring washing, discard the water layer,And then repeated washing once a few layers into the distillation kettle,After the toluene was distilled off, it was distilled under reduced pressure to obtain 206.1 kg of 2,3-difluoro-5-bromophenol,The product content of GC was 99.4%.The recovered toluene can be reused after drying. The total yield of the two-step reaction was 82.2%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 261762-35-0, its application will become more common.

Reference:
Patent; Zhejiang Linjiang Chemical Industry Co., Ltd.; Yi, Miao; Yin, Xin; Chen, Huanjun; Wang, Qijin; Xu, Xin; (8 pag.)CN106478377; (2017); A;,
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Synthetic Route of 5905-69-1,Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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.

Copper iodide (54 mg, 0.283 mmol) and Tetrakis(triphenylphosphine) palladium (105 mg, 0.091 mmol) were added. Lastly 1-bromo-4-(difluoromethoxy)benzene (0.750 g, 3.36 mmol) was added, the vial was covered with a teflon septa, an aluminum cap was crimped in place, and the assembly was set on a Biotage Emrys microwave instrument to irradiate at 80 C. for 30 minutes. The crude reaction was diluted with diethylether, washed with saturated ammonium chloride, and purified via column chromatography on a Yamazen W-Prep 2XY using 25% EtOAc in hexanes. Concentration by rotary evaporation afforded 500 mg of oil (96%); 1H NMR (400 MHz, DMSO-d6) delta ppm 3.03 (t, J=4.6 Hz, 4H) 3.73 (t, J=4.6 Hz, 4H) 7.13-7.14 (m, 1H) 7.16 (d, J=2.6 Hz, 1H) 7.17-7.19 (m, 2H) 7.22 (d, J=8.8 Hz, 2H) 7.24 (t, J=73.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H); MS (ES) m/z 348.2 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-(difluoromethoxy)benzene, its application will become more common.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
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These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)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. Quality Control of 1-Bromo-4-(difluoromethoxy)benzene

Step 4) 1-difluoromethoxy-4-{3-[3-(2-methoxy-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-methoxy-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (1.00 g, 2.70 mmol) was dissolved in THF (5 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (5 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (1.20 gm, 5.38 mmol), copper iodide (70 mg, 0.262 mmol), tetrakis(triphenylphosphine)palladium (140 mg, 0.120 mmol) and triethylamine (5.8 g, 98 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%-10% EtOAc in hexanes) afforded an oil 882 mg (46%). This material was used in next step without further characterization.

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

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
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Ether | (C2H5)2O – PubChem

Application of 261762-35-0, A common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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 1: Preparation of 8-(3,4-difluoro-5-methoxy-phenyl)-1,4-dioxa-8- azaspiro[4.5]decane To a mixture of 5-bromo-1,2-difluoro-3-methoxy-benzene (1.1 g, 4.93 mmol), 1,4-dioxa-8- azaspiro[4.5]decane (0.85 g, 5.92 mmol) and t-BuONa (0.95 g, 9.86 mmol) in 1,4-dioxane (10 mL) was added Pd2(dba)3 (92 mg, 0.10 mmol) and Ru-Phos (92 mg, 0.20 mmol) successively under N2. After being heated at 100 oC with stirring overnight, the reaction mixture was cooled down to rt, diluted with water (20 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 8-(3,4-difluoro-5-methoxy-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane (1.57 g) which was used in the next step directly without further purification.

The synthetic route of 261762-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
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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. Computed Properties of C9H13NO

General procedure: To a mixture of the corresponding secondary amines 14A-F (0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) and KI (8.6 mg, 0.052 mmol) in anhydrous CH3CN (12 ml) were added the appropriate intermediates 10-13 (0.5 mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water (40 mL) and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (20 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 CH2Cl2/CH3OH (100:1) as eluent to afford the corresponding scutellarein-O-alkylamine derivatives 15-18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6851-80-5, its application will become more common.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 – 366;,
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Related Products of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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.

2-Amino-3,5-difluorobenzoic acid (500 mg; 2.89 mmol), 10 ml of dry DCM, and TEA (1.61 ml; 11.55 mmol) were placed in a reaction flask under nitrogen. 4- (Trifluoromethoxy)benzylamine (0.529 ml; 3.47 mmol) was added slowly and then T3P (3.4 ml; 5.78 mmol; 50 % in EtOAc) was added keeping the temperature at rt. The mixture was stirred at rt overnight. The reaction mixture was diluted with DCM and washed three times with water. The organic phase was dried with a phase separator and evaporated to dryness to yield 1.09 g of 2-amino-3)5-difluoro-N-(4-(trifluoromethoxy)benzyl)benzamide. 1H-NMR (400 MHz, -DMSO): delta 3.33 (s, 6H), 4.45 (d, 2H), 6.24 (s, 2H), 7.22-7.40 (m, 4H), 7.41-7.51 (m, 2H), 9.02 (t, 1H).

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

Reference:
Patent; ORION CORPORATION; PRUSIS, Peteris; HOeGLUND, Lisa; TOeRMAKANGAS, Olli; HIETANEN, Ari; ARVELA, Riina; VESALAINEN, Anniina; HEIKKINEN, Terhi; WO2015/169999; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17715-69-4, name is 1-Bromo-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 17715-69-4, Computed Properties of C8H9BrO2

General procedure: A solution of 4-methoxybromobenzene (2.67 mmol)and cyclopent-2-en-1-one (3.2 mmol) in DMSO was stirred at ambient temperaturefor 10 min under nitrogen, and treated with Na2CO3 (8.01mmol) and tri-tert-butylphosphonium tetrafluoroborate (0.53 mmol).The reaction mixture was degassed with nitrogen for 10 min and treated withPd(PPh3)2Cl2 (0.13 mmol) and X-Phos (0.26mol), and stirred at 100 0C for 12 h. The reaction mixture was cooledto ambient temperature, diluted with water, and extracted with AcOEt (3 x 50ml). The combined organic layers were washed with brine, dried over anhydrousNa2SO4, and evaporated. Flash chromatograph on silica gel(AcOEt:cyclohexane 1:3) provided the Heck coupling product as brown solid (340mg, 68percent).

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-Bromo-2,4-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gowala, Tarak Nath; Pabba, Jagadish; Tetrahedron Letters; vol. 56; 14; (2015); p. 1801 – 1804;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H13NO2

41. Reaction of but-3-en-1-ol and (benzyloxy)acetaldehyde in the presence of sulfuric acid provided 2-[(benzyloxy)methyl]tetrahydro-2H-pyran-4-ol, which was oxidized with pyridinium chlorochromate to afford 2-[(benzyloxy)methyl]tetrahydro-4H-pyran-4-one. Subsequent reductive amination with 1-(2,4-dimethoxyphenyl)methanamine and lithium borohydride gave cis-2-[(benzyloxy)methyl]-N-(2,4-dimethoxybenzyl)tetrahydro-2H-pyran-4-amine. This was reacted with C13 and triethylamine, and the product was deprotected using trifluoroacetic acid to yield N-{cis-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-4-yl}-6-chloro-3-nitroquinolin-4-am ine; hydrogenation of the nitro group over platinum(IV) oxide afforded N4-{cis-2-[(benzyloxy)methyl]tetrahydro-2H-pyran-4-yl}-6-chloroquinoline-3,4-diamine.

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 20781-20-8.

Reference:
Patent; Pfizer Inc.; Galatsis, Paul; Henderson, Jaclyn Louise; Kormos, Bethany Lyn; Kurumbail, Ravi G.; Reese, Matthew Richard; Stepan, Antonia Friederike; Verhoest, Patrick Robert; Wager, Travis T.; Pettersson, Martin Youngjin; Garnsey, Michelle Renee; (150 pag.)US2017/73343; (2017); A1;,
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