Month: August 2021

Electric Literature of 13940-96-0, 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. 13940-96-0, name is 4-Phenoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of Intermediate AC (395 mg,1 .97 mmol) in EtOH (10 mL) was added 1,3- bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (427 mg,2.07 mmol),and the mixture was heated to reflux for 18h. After cooling to r.t.,Eta0 was added and the resultant solid collected by filtration (washing with EtOH/Et20) to afford the title compound as an off-white solid (436 mg,78%).1H NMR 6H (500 MHz,DMSO-d6) 11 .61 (br s,2H),7.40 (d,J = 8.5 Hz,1 H),7.38 – 7.32 (m,2H),7.09 – 7.03 (m,2H),6.97 – 6.92 (m,2H),6.81 (dd,J = 8.5,2.4 Hz,1 H),3.75 (s,3H); LCMS (Method A): 3.24 min,(284.2,MH+).

The synthetic route of 4-Phenoxybenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLOBACHEM NV; URCH, Christopher, John; JACKSON, Victoria, Elizabeth; JORDAN, Linda; BURGIN, Ryan, Neil; (180 pag.)WO2019/141980; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 105529-58-6, name is 4-Bromo-2-fluoro-1-(trifluoromethoxy)benzene, 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 105529-58-6, Recommanded Product: 4-Bromo-2-fluoro-1-(trifluoromethoxy)benzene

3-(3-fluoro-4-trifluoromethoxyphenyl)-2-methylpro panal [in the formula (II), W represents 3-fluoro-4-trifluoromethoxyphenyl group] was prepared using the method described by the reaction formula (D) . 7 mg (0.04 mmol) of palladium chloride (II) and 20 mg (0.076 mmol) of triphenylphosphine were dissolved in 2 ml of N,N-dimethylformamide at 120C under nitrogen atmosphere, and allowed to cool to 50C. The solution was admixed with 1.0 g (3.9 mmol) of 3-fluoro-4-trifluoromethoxybromobenzene, 420mg (5.8mmol) of methallyl alcohol and 390 mg (4.6 mmol) of sodium hydrogencarbonate, and was stirred at 130C for 3 hours. After standing to cool, the resultant solution was admixed with water and extracted with benzene. The separated benzene phase was washed with water and saturated brine successively, and dried over sodium sulfate anhydride. After solvent removal by distillation under a reduced pressure, 870 mg of an oily substance was obtained. The oily substance was purified by using silica gel column (Merck Silica gel 60, 230-400 mesh, Merck Co., eluent composition: Hexane/AcOEt=15/1). This gave 500 mg of 3-(3-fluoro-4-trifluoromethoxyphenyl)-2-methylpropanal as an oily substance. The yield was 51.3%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; KUREHA KAGAKU KOGYO KABUSHIKI KAISHA; EP1375483; (2004); A1;,
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Some common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, molecular formula is C8H11NO, 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. HPLC of Formula: C8H11NO

4-Methoxybenzylamine (600 g, 4.37 mol) and 4-methoxybenzaldehyde (532 mL, 4.37 mol) were added to a 10 L RBF at ambient temperature. An exotherm was observed and a white precipitate formed. The mixture was stirred for 1 h and then anhydrous EtOH (4.8 L) was added. After an additional 15-3 0 mm at RT, sodium borohydride granules (99 g, 2.62 mol) were added portionwise over 2 h (during the addition of the NaBH4, the internal temperature of the reaction rose to 42 C), and the mixture was further stirred at RT overnight. The reaction was then quenched slowly with water (600 mL) and then was concentrated in vacuo. The residue was partitioned between water (4 L) and DCM (4 L), and the aqueous layer was extracted with more DCM (2 x 2 L). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide 361.01 (1112 g, 99% yield) as a semi-solid. The material was used directly in the next step without futher purification. 1H-NMR (400 MHz, CDC13) oe 7.28 (t, J=7. 1 Hz, 4H), 6.89 (d, J=8.6 Hz, 4H), 3.83 (m, 6H), 3.76 (s, 4H). LCMS-ESI (pos.) m/z: 258.4 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2393-23-9, its application will become more common.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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: 588-63-6

General procedure: Bromoethane (0.45 mL, 6 mmol) was dropped to the mixture of 8 (0.86 g, 3 mmol), K2CO3 (0.83 g, 6 mmol) and KI (catalytic amount) in CH3CN. The mixture was stirred at 35°C for 8 h. he reaction mixture was filtered. The filtrate was concentrated and purified by chromatography on a silica gel column, eluting with a mixture of ethyl acetate and petroleum ether to give the desired product. 4.1.4.23. (E)-Ethyl 3-{5-[(biphenyl-4-ylmethyl)(3-phenoxypropyl)amino]methyl}furan-2-ylacrylate (12i). Compound 12i (1.29 g, 86.6percent yield) was synthesized from 11 (1.26 g, 3 mmol) and (3-bromopropoxy)benzene (0.77 g, 3.6 mmol) according to the procedure used to synthesize 9a; oil; MS (EI) m/z 495 (M+).

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

Reference:
Article; Feng, Taotao; Wang, Hai; Su, Hong; Lu, Hui; Yu, Liqin; Zhang, Xiaojin; Sun, Haopeng; You, Qidong; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5339 – 5354;,
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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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Methoxyphenoxy)ethylamine

2-(2-Methoxyphenoxy)ethyl amine (15.09 g), N,N-diisopropylethyl amine (10.8 g), 4-(oxiran-2yl-methoxy)-9H-carbazole (20.0 g) and monoglyme (30 mL) were heated to 80-850C. After 8-12 hours, the reaction mixture was cooled to room temperature and ethyl acetate (40 mL) was added. The contents were cooled to 0-50C. The solid is filtered after slurry in ethylacetate to get crude Carvedilol (100 mL). (Purity: 98.62%; Yield: 36.26 %; Bis-impurity: 0.65%.)

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INOGENT LABORATORIES PRIVATE LIMITED1; WO2009/157015; (2009); A2;,
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Reference of 2930-05-4, 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. 2930-05-4 name is 2-((Benzyloxy)methyl)oxirane, 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.

In a glass RBF equipped with a Teflon- coated magnetic stirrer and a reflux condenser was dissolved 2-benzyloxymethyl-oxirane (1 eq.) in a 3:1 (v/v) solution (0.08 M) of methanol and water. To this was then added sodium azide (2 eq.) and ammonium chloride (1.5 eq.), and the resulting mixture was heated at reflux for 14 h. The reaction solution was cooled to RT and diluted with tBuOMe. The organic layer was separated, washed further with sat. aq. NH4C1, dried over MgSO4, and filtered. Concentration of the filtrate in vacuo delivered the crude product as a pale yellow oil. Further purification by way of column chromatography (Si02, gradient elution, 9:1 (v/v) Hex: EtOAc – 3:7 (v/v) Hex:EtOAc) furnished the desired product as a colorless oil (71% yield).

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

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (2017); 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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, A new synthetic method of this compound is introduced below., Quality Control of 2-(Benzyloxy)-1-ethanamine

Example 25; 5-cvclopropyl-2-(4-fluorophenyl)-6-(N-((2-hvdroxy-1 ,2-oxaborolan-4- yl)methyl)methylsulfonamido)-N-(2-hvdroxyethyl)benzofuran-3-carboxamideStep 1: N-(2-(benzyloxy)ethyl)-5-cyclopropyl-2-(4-fluorophenyl)-6- (methylsulfonamido)benzofuran-3-carboxamide5-Cyclopropyl-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (1 .0 g, 2.568 mmol) was stirred in dry DMF (15 mL) at ambient temperature with DIPEA (0.730 g, 5.650 mmol) and HATU (1.71 g, 3.082 mmol). After stirring for 15 minutes, benzyloxymethanamine (1 .552 mg, 10.272 mmol) in 15 mL of THF was added. The reaction mixture was stirred for another 2 hours and diluted with EtOAc (30 mL) and water (30 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (30 mL x2). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by columnchromatography (eluting with 0-50% ethyl acetate in petroleum) to give N-(2- (benzyloxy)ethyl)-5-cyclopropyl-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3- carboxamide (1.4 g, crude, 104% yield).

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; GLAXO GROUP LIMITED; JOHNS, Brian Alvin; SHOTWELL, John Brad; HAIGH, David; WO2012/67663; (2012); A1;,
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Synthetic Route of 19056-40-7, 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 19056-40-7 as follows.

Reference 2; Synthesis of 3-methoxy-4-(2-methylpyridin-4-yl)benzenamineStep l4-Bromo-3-methoxyaniline (3.70 g, 18.3 mmol; Aldrich) was dissolved in N,N- dimethylformamide (40 mL, 500 mmol) and triethylamine (2.68 mL, 19.2 mmol) was added. Acetic anhydride (1.81 mL, 19.2 mmol) was added and the reaction mixture stirred for 5 hours. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered and diluted with hexames. The layer was concentrated to minimal volume and the resultant slurry was filtered and washed with hexanes to yield N-(4- bromo-3-methoxyphenyl)acetamide as a light peach solids.

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/75874; (2009); A1;,
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Reference of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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.

[0187] Into a 5 L 3-necked roundbottom flask, was placed a solution of l-(3- bromopropoxy)benzene (250 g, 1.16 mol) in THF (600 ml). To this was added dimethylamine in water (1 L 33percent). To the mixture was added KOH (200 g, 4.46 mol). The resulting solution was allowed to react, with stirring, for 5 hours while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (EtOAc/PE = 1 :3). The resulting solution was extracted five times with 200 ml of EtOAc and the organic layers combined. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 20Og of crude N,N-dimethyl-3-phenoxypropan-l -amine as light yellow oil.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); A1;,
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Application of 801282-00-8, These common heterocyclic compound, 801282-00-8, name is 2-Fluoro-3-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.

[00385] Intermediate 30. l-(3-Chloro-2-fluorophenyl)-5-methoxy-lH-l,2,3-triazole-4- carboxylic acid: To a solution of 2-fluoro-3-methoxyaniline (1 g, 7.09 mmol) in TFA (10 mL) and water (5 mL) at 0 C was added an aq. solution of NaN02 (0.733 g, 10.63 mmol) dropwise. The resulting mixture was stirred at 0 C for 0.5 h and NaN3 (0.921 g, 14.17 mmol) was added portionwise. The reaction mixture was gradually warmed to rt and stirred for 4 h. The reaction was quenched with water (150 mL) and extracted with EtOAc (2×100 mL). The organic layer was washed with sodium phosphate solution (10%) and brine (50 mL), dried, and concentrated. The resulting brown oil was re- dissolved in DMSO (20 mL) and added t-butylpropiolate (1 mL) followed by K2CO3 (1 g), Cu(OAc)2 (0.2 g), and sodium ascorbate (100 mg). The resulting mixture was stirred at rt overnight. The reaction was quenched with water (200 mL) and extracted with EtOAc (2 x 100 mL). The organic layer was dried and concentrated. The residue was purified by silica gel chromatography to yield the desired product as brown oil. 1H NMR (400 MHz, CDCI3) delta 13.19 (br. s., 1H), 7.36 – 7.20 (m, 2H), 7.17 – 6.95 (m, 1H), 6.76 (td, J = 8.1, 1.3 Hz, 1H), 3.91 (s, 3H), 1.74 – 1.49 (m, 10H). MS(ESI) m/z: 238.0 (M+H)+.

The synthetic route of 801282-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
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