Author: Jessica.F

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. 4003-89-8, name is 7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4003-89-8

(b) An amount of 3.01 g of 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene is reacted under stirring at room temperature for 4 days with 2.04 g of styrene. After addition of ethyl acetate, to the reaction mixture there is added a saturated solution of hydrogen chloride in isopropyl alcohol to obtain the 2-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride. Yield: 31% of the theoretical value.

The synthetic route of 4003-89-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanofi; US4707497; (1987); A;,
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Application of 1462-37-9, These common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)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.

Stage 1; – /V-{1-[2-(Benzyloxy)ethyl]piperidin-4-yl}-4-{[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6- oxo-5,6,7,8-tetrahydropteridin-2-yl]amino}-3-methoxybenzamide To a solution of Intermediate C (300mg, 0.59mmol) in DMF (3ml), was added benzyl-2- bromoethylether (0.09ml, 0.59mmol), K2CO3 (163mg, 1.18mmol) and NaI (catalytic amount). The reaction mixture was stirred for 18 hours at 50 °C, cooled to RT and partitioned between EtOAc (10ml) and water (10ml). The aqueous layer was re-extracted with EtOAc (2 x 10ml) and the combined organic layers were washed with water (2 x 10ml), brine (2 x 15mL), dried (MgSO4), and concentrated under reduced pressure. Purification by column chromatography (5 – 10percent MeOH in DCM) afforded the title product (213mg, 56percent). ESMS m/z 642 [M+H]+

Statistics shows that ((2-Bromoethoxy)methyl)benzene is playing an increasingly important role. we look forward to future research findings about 1462-37-9.

Reference:
Patent; CHROMA THERAPEUTICS LTD.; WO2008/50078; (2008); A1;,
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Electric Literature of 16452-01-0, 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. 16452-01-0, name is 3-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the corresponding carboxylic acid (1.0 equiv.), an appropriate amine (2 equiv.), propylphosphonic anhydride (4 equiv.) and N,N- diisopropylethylamine (3.0 equiv.) was stirred in THF or acetonitrile at an elevated temperature for 3 – 16 h. After complete reaction the mixture was purified by silica gel chromatography or by preparative liquid chromatography

The chemical industry reduces the impact on the environment during synthesis 3-Methoxy-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; CAZARES-KOeRNER, Armando; HELLEDAY, Thomas; VISNES, Torkild; WALLNER, Olov; KOOLMEISTER, Tobias; (294 pag.)WO2019/166639; (2019); A1;,
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Electric Literature of 126-38-5,Some common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, molecular formula is C5H11BrO2, 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 10 Synthesis of 8-(4-chloro-3-ethoxycarbonylphenyl)-7,8-dihydro-2-methyl-5-trifluoromethylimidazo[1,2-a]pyrimidin-7-one (The compound No.13) STR14 A mixture of 2-amino-3-(4-chloro-3-ethoxycarbonylphenyl)-3,4-dihydro-6-trifluoromethylpyrimidin-4-one (0.5 g), bromoacetone dimethyl acetal (0.6 g) and DMF (10 ml) was heated for 5 hours at 130 C. with stirring. The solvent was distilled off under reduced pressure. The residue was added with water and extracted with ethyl acetate. The extract layer was washed with water and dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a preparative thin-layer plate of alumina (developing solvent: ethyl acetate/hexane=3/7) to give the compound of interest (0.11 g). 1 H-NMR (ppm) 1.38(t, J=7 Hz, 3H), 2.22(s, 3H), 4.39(q, J=7 Hz, 2H), 6.62(s, 1H), 7.00(s, 1H), 7.48(dd, J=8, 3 Hz, 1H), 7.64(dd, J=8, 0.5 Hz, 1H), 7.95-7.96(m, 1H) [CDCl3 ].

The synthetic route of 126-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissan Chemical Industries, Ltd.; US6165942; (2000); A;,
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Application of 20265-97-8, 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. 20265-97-8, name is 4-Methoxyaniline hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-methyl-4?-hydroxyazobenzene (Azo1). 6,8 g (0.05 mol) as hydrochloride was dissolvedin 100 mL hydrochloric acid (2M). Solution was cooled by ice bath up to0C and solution of 3,3 g (0.05 mol) sodium nitrite in minimal volume of water wasadded slowly. To the cooled solution of phenol 4,4 g (0.05 mol) in water the diazoniumsalt was added under stirring. Yellow azodye precipitate was filtered, washedby cooled water and dried. Substance purification was made by recrystallization fromisopropanol.

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

Reference:
Article; Tarasenko, Vitaliy; Nadtoka, Oksana; Syromyatnikov, Vladimir; Molecular Crystals and Liquid Crystals; vol. 590; 1; (2014); p. 97 – 104;,
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Electric Literature of 578-57-4,Some common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, molecular formula is C7H7BrO, 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 10 mL sealed vial was added Cu(OAc)2·H2O (10 mg, 0.05mmol), N-methoxy-1H-pyrrole-2-carboxamide (7 mg, 0.05 mmol), aryl bromide (1.0 mmol), amine (3.0 mmol), K3PO4 (318 mg, 1.5 mmol),PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 C for 12 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 25 mL) and water (20 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.

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-2-methoxybenzene, its application will become more common.

Reference:
Article; Huang, Manna; Hou, Jianying; Yang, Ruiqiao; Zhang, Liting; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 24; (2014); p. 3356 – 3364;,
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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. 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 25245-34-5

To a solution of LDA (7.4 mL, 1.1 eq) in THF (15 mL) were added furan (15 mL) and l-bromo-2,5-dimethoxybenzene (2.16 g, 10 mmol) in turn at -78 C. The mixture was stirred at this temperature for 30 mins and quenched with water and then the mixture was allowed to warm up to rt and extracted with ethyl ether (50 mL x 3). The combined organic layers were dried over anhydrous Na2SC>4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (Hex/EtOAc (v/v) = 1/1) to give the title compound as a white solid (2.1 g, 86%). The compound was characterized by the following spectroscopic data: NMR (400MHz, CDC13) delta 7.06 (2H, s), 6.97 (2H, s), 6.54 (2H, s), 5.92 (2H, s), 3.78 (6H, s) ppm.

The synthetic route of 25245-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; HU, Bailin; LI, Shifeng; WU, Xiwei; TANG, Changhua; WANG, Chenglin; FANG, Qinghong; YU, Quanxing; ZHANG, Zhikeng; WO2014/131315; (2014); A1;,
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Electric Literature of 944317-92-4, A common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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 500 mL dry flask was charged with 2-bromo-5-fluoro-4-isopropylanisole (compound of formula 4, Scheme 3) (24.6 g, 0.1 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri-isopropylborate (32 mL, 0.14 mol) was added. The mixture was cooled to -80 C. Then 10 M n-BuLi in hexanes (12.5 mL, 0.125 mol) was added slowly, maintaining a temperature below -55C. Thirty minutes after completion of the n-BuLi addition, the reaction was warmed to -35C and quenched into 3 M H2SO4 solution (75 mL, 0.225 mol). DIPE (200 mL) was added to the mixture to dilute the organic layer. The mixture was stirred (15 min) and the aqueous layer was cut away. The organic layer was washed with 3.0 M H2SO4 (75 mL). The organic phase was extracted three times with 1 M NaOH (200 mL first and then 50 mL and 50 mL). The three NaOH extractions were combined, diluted with 2-propanol (85 mL), and cooled to 15 C. Then the solution was slowly acidified to pH ~ 2 using 3 M H2SO4 (70 mL) while maintaining temperature at 15-20 C. The resulting slurry was stirred for 1 hour and then filtered. The filter cake was washed with water (3 x 30 mL) and dried under an air flow for 1 day. The white crystalline solid was isolated to yield boronic acid of formula 5 (Scheme 3) (19.23 g, 91%): mp 100-102 C; 1H NMR (CDCl3) delta 1.25 (d, J = 6.9 Hz, 6H), 3.17 (sept., J = 6.9 Hz, 1H), 3.88 (s, 3H), 5.83 (s, 2H), 6.59 (d, J =12.4 Hz, 1H), 7.72 (d, J = 6.6 Hz, 1H). The impurity 5-ethyl-4-fluoro-2-methoxyphenylboronic acid (~4%), which is formed from 1-bromo-5-ethyl-4-fluoro-2-methoxybenzene (BrMET) present in the starting material under the conditions described in Step 4, was detected in the product.

The synthetic route of 944317-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2468736; (2012); A1;,
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Application of 157869-15-3, 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. 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

1 k (0.3 mmol, 67 mg), [RhCp*Cl2] 2 (0.015 mmol, 9.3 mg) and hexafluoroisopropanol (2 mL) were sequentially added to a 15 mL reaction tube.The reaction tube was sealed in an air atmosphere, and the reaction was stirred at 120 C for 20 h. After the completion of the reaction, the reaction tube was cooled to room temperature, and 10 mL of water was added thereto, followed by extraction with ethyl acetate (10 mL × 3), and the organic phase was washed successively with water and brine, and dried over anhydrous sodium sulfate. filter,Spin dry, separated by silica gel column (petroleum ether / ethyl acetate = 5 / 1)The white solid product 2k (35 mg, 72%).

The chemical industry reduces the impact on the environment during synthesis 2-((4-Methoxyphenyl)ethynyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Henan Normal University; Fan Xuesen; Jia Ruixue; Zhang Xinying; Li Bin; (18 pag.)CN110183443; (2019); A;,
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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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., SDS of cas: 321-28-8

EXAMPLE 1 Preparation of 1-(3-Fluoro-4-Methoxy-Phenyl)-Hexan-1-One; 2-Fluoroanisole (3.15 g, 25.0 mmol) is dissolved in dry dichloromethane (25 mL). While stirring the resulting solution under nitrogen, aluminum chloride is added (3.92 g, 29.4 mmol). This solution is cooled with a cold water bath and hexanoyl chloride (3.87 g, 28.8 mmol) is added drop wise such that the internal temperature is maintained at or below 20 C. Upon complete of addition, the reaction is stirred 30 minutes at room temperature. The dark orange solution is cooled to -10 C. and slowly quenched by the addition of water (25.0 mL) while keeping the internal temperature below 0 C. The mixture is transferred to a separatory funnel, the organic layer (bottom) is collected and the aqueous discarded. The organic solution is then washed with 5N NaOH (12.5 mL) and again with water (12.5 mL). The crude organic is concentrated by vacuum distillation and diluted with heptane to a final volume of about 20 mL. The slurry is heated until all solids are dissolved and allowed to cool to room temperature. The product crystallizes upon cooling. The slurry is further cooled to 0 to 5 C. for one hour and filtered. The wet cake is washed with cold (0 C.) heptane (2×2.5 mL) and the product dried under vacuum.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huffman, Mark A.; Qin, Xue-Zhi; Rosen, Jonathan D.; US2006/247319; (2006); A1;,
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