Month: August 2021

Related Products of 589-10-6, These common heterocyclic compound, 589-10-6, name is (2-Bromoethoxy)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.

General procedure: To a stirred solution of 1-(2-pyridyl)-b-carboline (0.245 g,1 mmol) in 10 mL DMF, sodium hydride (50% in mineral oil, 0.048 g,1 mmol) and bromo-hydrocarbon (1 mmol) was added. The reactionmixturewas stirred at room temperature for 1 h. After reactionwas finished, the mixture was poured into ice water and extractedwith ethyl acetate. The organic layer was washed with water anddried. Removal of the solvent gave the crude product that waspurified by silica gel column (dichloromethane: methanol 100:1 as the eluent). The solvent was removed and the product wasobtained.

Statistics shows that (2-Bromoethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 589-10-6.

Reference:
Article; Lu, Xing; Liu, Yan-Cheng; Orvig; Liang, Hong; Chen, Zhen-Feng; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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Application of 39538-68-6, These common heterocyclic compound, 39538-68-6, name is 2-Methoxy-4-methylaniline, 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 a solution of cupric bromide (6.35 g; 28.4 mmol) in acetonitrille (25 ml_) was added tert- butyl nitrite (2.85 ml 24.06 mmol) and the mixture was heated at 65^ under a nitrogen atmosphere. A solution of 2-methoxy-4-methylaniline (3 g; 21 .87 mmol) in acetonitrile (25 ml_) was added carefully and the mixture was stirred for 20 min at 65 ‘O. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed (x 3) with an aqueous solution of ammonia 5%, water, a solution of ethylenediaminetetraacetic acid, water, brine and the mixture was concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2 – 50 %) in heptane furnished 2.32 g (53 %) of the title compound as a yellow oil.

Statistics shows that 2-Methoxy-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 39538-68-6.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; CHALTIN, Patrick; DEBYSER, Zeger; DE MAEYER, Marc; MARCHAND, Arnaud; MARCHAND, Damien; SMETS, Wim; VOET, Arnout; CHRIST, Frauke; WO2011/15641; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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 74654-07-2, Computed Properties of C7H17NO3

(iv) tert-Butyl (4-((2-((3-ethvnyl-5-((2-(2-(2-methoxyethoxy)ethoxy)ethyl)carbamoyl)- phenyl)amino)pyridin-4-yl)oxy)naphthalen-1-yl)carbamateHATU (500 mg, 1.315 mmol) was added to a stirred solution of the product from step (iii) above (500 mg, 1.009 mmol), 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (277 mg, 1.695 mmol) and triethylamine (250 pL, 1.796 mmol) in N,N-dimethylformamide (10 mL). The mixture was stirred at rt for 18 h. The mixture was diluted with EtOAc (50 mL) and washed with water (50 mL), 20% brine (3 x 50 mL) and saturated brine (50 mL). The organic phase was dried (MgSC ), filtered and concentrated under reduced pressure. The crude product was purified by chromatography on the Companion (40 g column, EtOAc) to afford the sub-title compound (580 mg) as a tan foam.LCMS m/z 641 (M+H)+(ES+); 639 (M-H)”(ES”)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, and friends who are interested can also refer to it.

Reference:
Patent; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew Colin Thor; THOM, Stephen Malcolm; BAKER, Thomas Matthew; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; RIGBY, Aaron; WO2015/92423; (2015); A1;,
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Electric Literature of 63057-72-7,Some common heterocyclic compound, 63057-72-7, name is 1-(Benzyloxy)-4-bromo-2-methoxybenzene, molecular formula is C14H13BrO2, 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.

1 -(benzyloxy)-4-bromo-2- methoxybenzene (18.2 g, 62 mmol) was suspended in 162 mL methanol and 18 mL water. N- Iodosuccinimide (18. lg, 81 mmol) and trifluoroacetic acid (3.8 mL, 50 mmol) were added sequentially. The mixture was warmed to 35 C and stirred for 7 hours in the dark. Water (54 mL) was added dropwise over 15 minutes, then the mixture was allowed to cool slowly to room temperature while stirring overnight. The crystalline product was filtered, and rinsed with a 6:4 mixture of methanol: water (2 x 20 mL). The solids were dried in vacuo at 50 C to provide 1- (benzyloxy)-4-bromo-5-iodo-2-methoxybenzene. 1H NMR (400 MHz, Chloroform-d) delta 7.45 – 7.32 (m, 5H), 7.29 (s, 1H), 7.10 (s, 1H), 5.07 (s, 2H), 3.84 (s, 3H). MS (m/z) 419.8 [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-(Benzyloxy)-4-bromo-2-methoxybenzene, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CANALES, Eda; CURRIE, Kevin S.; KATO, Darryl; LI, Jiayao; LINK, John O.; METOBO, Samuel E.; SAITO, Roland D.; SCHROEDER, Scott D.; SHAPIRO, Nathan; TSE, Winston C.; WU, Qiaoyin; (262 pag.)WO2018/144605; (2018); A1;,
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Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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 C7H5BrF3NO

To a cooled (0C) solution of phosgene (20% solution in toluene, 2.76 ml, 5.52 MMOL) in dry DICHLOROMETHANE (75 ml) was added, under an argon atmosphere, methyl 4-amino-2- methoxybenzoate (1 G, 5.52 MMOL) in one portion, followed by a dropwise addition of diisopropylethylamine (1.92 ML, 11.04 MMOL). The mixture was stirred for 15 minutes at 0C prior to the addition of 2-bromo-4 (trifluoromethoxy) aniline (0.83 ML, 5.52 MMOL). The reaction mixture was stirred at 0C for a further 2 hours and then was allowed to stir at room temperature overnight. The organic phase was washed with 1 N aq. HCI (2x), sat. aq. NAHCO3, dried over MGS04 and concentrated in vacuo to give a solid residue which was recrystallized in hot acetonitrile. The fine crystalline solid was filtered off, washed with cold acetonitrile and dried in vacuo to give the title compound Ex 106 as a pale-orange solid (1. 64G, 3.54 mmol, 64%). ‘H-NMR (DMSO-d6) : 6 3.74 (s, 3H), 3.80 (s, 3H), 7.02 (d, 1H), 7.38 (s, 1H), 7.42 (d, 1H), 7.69 (d, 1H), 7.74 (s, 1H), 8.17 (d, 1H), 8.36 (s, 1H), 9.85 (s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 175278-17-8, its application will become more common.

Reference:
Patent; 7TM PHARMA A/S; LITTLE, Paul Brian; WO2004/48319; (2004); A1;,
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Reference of 1758-46-9, These common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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.

[Example 6] Compound D (150 mg, 483 mumol), 2-phenoxyethylamine (127 mul) and sodium hydrogencarbonate (400 mg) were added to DMSO (3 ml), and the mixture was stirred at 100°C for 27 hr. After stirring, the reaction mixture was added dropwise to cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and concentrated, and the residue was washed by suspending in ethyl acetate to give the object compound of 2-(2-phenoxyethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-(pyridin-3-yl)nicotinonitrile (82 mg). 1H-NMR (400MHz, DMSO-d6) delta (ppm): 12.06 (1H,br-s), 10.22 (1H,br-s), 8.72-8.69(2H,m), 7.98(1H,dd), 7.65(1H,dd), 7.29-7.23(2H,m), 6.96-6.90(3H,m),6.16(1H,br-s),4.23(2H,t),3.67(2H,t),2.22(3H,s). m/z=412 (M+H)

The synthetic route of 1758-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1876178; (2008); A1;,
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Application of 5905-69-1, 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Bromo-4-(difluoromethoxy)benzene 6 (2.23 g, 10 mmol), potassium acetate (30.0 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (11.0 mmol) and Pd(PPh3)4 (0.5 mmol) are added to a 40-mL Schlenk flask equipped with a stir bar. The flask is evacuated and backfilled with nitrogen several times. 1,4-Dioxane (10 mL) is added by syringe. The Schlenk flask is sealed and heated at 1500C for 20 min in a microwave oven. After the reaction is complete, the solvent is removed under vacuum. The residue is dissolved in DCM (200 mL) and washed with water. The organic phase is dried with anhydrous Na2SO4, filtered and concentrated to yield a crude product. Purification by silica gel column chromatography (EtOAc : hexanes, gradient from 0% to 20%) affords 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 7. 1H NMR (400MHz, CDCl3) delta 7.74 (d, J = 8.4 Hz, 2H), 7.02 (d, J = 8.4 Hz, 2H), 6.48 (t, J = 73.6 Hz, IH), 1.27 (s, 12H). MS (m/z) (M+l)+: 271.1.

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

Reference:
Patent; IRM LLC; WO2009/26276; (2009); A1;,
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Synthetic Route of 29578-39-0, A common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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-fluoro-5-methoxy-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane A mixture of 3-bromo-5-fluoroanisole (87.6 g, 0.49 mol), 1,4-dioxa-8-azaspiro[4.5]decane hydrochloride (100.0 g, 0.49 mol), t-BuONa (117.2 g, 1.22 mol), BINAP (12.1 g, 0.02 mol) and Pd2(dba)3 (8.9 g, 0.01 mol) in toluene (1.3 L) was heated at 100 oC with stirring under nitrogen for 16 hrs. The reaction mixture was cooled down to rt and filtered. The filtrate was diluted with DCM (3.0 L), and washed with H2O (500 mL) and brine (200 mL). The organic layer was dried over anhydrous Na2SO4, concentrated in vacuo and purified by the flash column chromatography to give 8-(3-fluoro-5-methoxy-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane (78.2 g) as a yellow oil.

The synthetic route of 29578-39-0 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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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. 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, A new synthetic method of this compound is introduced below., SDS of cas: 35896-58-3

General procedure: A solution of compounds 1, 4, 5 (2.5 mmol) in THF (10 mL) was diluted with water (5 mL), and an excess solution of cerricammonium nitrate (CAN) (3.9 g, 7 mmol) in 10 mL water was added at 0 C. The mixture was stirred at room temperature for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the THF was removed under a vacuum at 40 C, and the crude mixture was extracted with three portions of CH2Cl2 (20 mL). The orange extracts were washed with brine until neutrality, then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude products were purified by a silica-gel column chromatography with petroleum ether and EtOAc as eluent to give the desired benzoquinones 2, 7, 6.

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:
Article; Wang, Jin; Li, Shuo; Yang, Tao; Yang, Jian; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 710 – 713;,
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54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. Safety of 1-Bromo-2-(2-methoxyethoxy)ethane

To a solution of alkyl bromide in dry DMF would be added sodium azide, and the reaction mixture would be stirred at room temperature for 16 h. After completion of the reaction, the contents would be diluted with ethyl acetate and washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo.; 1-Azido-2-(2-methoxy-ethoxy)-ethane (607 mg) was prepared by following General Procedure U starting from 1-bromo-2-(2-methoxy-ethoxy)-ethane (1.0 g) and sodium azide (1.07 g). The crude product was used in the next step without further purification.

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HIGH POINT PHARMACEUTICALS, LLC; US2011/201604; (2011); A1;,
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