Month: May 2021

Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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. Product Details of 36865-41-5

To a solution of 4-bromo-1H-pyrazole (1.5 g, 10 mmol) in DMF (15 mL) were added cesium carbonate (5.1 g, 16 mmol) and 1-bromo-3-methoxypropane (1.6 mL, 14 mmol) . The mixture was stirred at rt for 8 h and diluted with water (30 mL) . The resulting mixture was extracted with DCM (30 mL × 3) . The combinded orgainc layers were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 2/1 to give a light yellow oil product (2.1 g, 94) .[1268]MS (ESI, pos. ion) m/z: 219.1, 221.1 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36865-41-5, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (2016); A1;,
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Related Products of 446-59-3, A common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-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.

To the dried reaction flask was added magnesium dust (600 mg, 24.9 mmol), a small portion of iodine and anhydrous tetrahydrofuran (10 mL), and the reflux condenser was charged and protected with nitrogen. -methoxybenzene (0.5 g) followed by the addition of 2-bromo-1-fluoro-3-methoxybenzene (2.5 g, 12.2 mmol) and freshly distilled 1,3-cyclopentadiene (1.05 g, 17.56 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) and placed in a constant pressure dropping funnel to slowly dropwise and the reaction system was kept slightly refluxed. After completion of the dropwise addition, the reaction system was heated to reflux for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (10 mL) and extracted with ethyl acetate (60 mL x 2). The organic phase was washed with saturated brine (30 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography (eluted with petroleum ether) to give the title compound (1.43 g, 56%) as a colorless liquid

The synthetic route of 446-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Dongguan Dongyangguang Pharmaceutical Research And Development Co., Ltd.; Zhou Pingjian; Wang Xiaojun; Yang Chuanwen; Lin Jihua; Cao Shengtian; Yang Xinye; Zhang Yingjun; (34 pag.)CN106916091; (2017); A;,
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Synthetic Route of 18800-30-1, 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. 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: tert-butyl 4-(2-(4-bromophenoxy)ethyl)-3-methylpiperazine-1-carboxylateToan 8mL scintillation vial were added 1-bromo-4-(2-bromoethoxy)benzene (2.80g, 10.0mmol), 4-N-Boc-2-methylpiperazine (2.00g, 10.0mmol), and cesium carbonate(7.5g, 20.0mmol) in anhydrous dimethylformamide (5.0 mL). Reaction slurry was stirred at RT for 48hrs, TLC and MS confirmingpresence of the desired intermediate. Quenched with water 20 (50mL) and extractedwith ethyl acetate(3x100mL). Organics were combined, washedwith additional water (50mL), brine (50mL), dried over Na2S04 and filtered. Solventwas removed and yellow oil was carried forward withoutpurification. ESI-LCMS m/z calculated for C18H27BrN203:expected 399.33;found 400.2 [M+Ht.

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-4-(2-bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE INSTITUTE FOR DRUG DELIVERY; CORMAN, Michael L.; HUNGERFORD, William M.; GOLEBIOWSKI, Adam; BECKETT, Raymond P.; MAZUR, Marzena; OLEJNICZAK, Sylwia; OLCZAK, Jacek; WO2015/95701; (2015); A1;,
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Application of 2734-70-5,Some common heterocyclic compound, 2734-70-5, name is 2,6-Dimethoxyaniline, molecular formula is C8H11NO2, 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 mixture of benzoic acids 4 (7) (4 mmol),1-ethyl-3-(3-dimethyllaminopropyl) carbodiimide hydrochloride (4.8 mmol) and N-hydroxybenzotrizole (0.48 mmol) wereadded amines (4.8 mmol) at room temperature. The reaction mixture was stirredfor overnight and washed with water successively. The organic layer was driedover anhydrous sodium sulfate. Then the solvent was removed in vacuo to affordcrude compounds 5 (8).

The synthetic route of 2734-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jiling; Wu, Dang; Xu, Xiaoyong; Huang, Jin; Shao, Xusheng; Li, Zhong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 3064 – 3066;,
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Related Products of 6346-09-4, 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of appropriate amine (11.2 mmol) in dry CH2Cl2 (11 ml) CDI (2.0 g, 12.3 mmol) wasadded. The mixture was stirred at room temperature for 120 h. To the resulting solution 4,4-diethoxybutyl-1-amine (1.80 g, 11.2 mmol) was added and the reaction mixture was stirred at roomtemperature for additional 72 h. Solvent was evaporated invacuo. Residue was througly washedwith water, filtered and dried in vacuo (2 h, 0.01 torr) to give the title compound 1.

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

Reference:
Article; Gazizov; Smolobochkin; Voronina; Burilov; Pudovik; Tetrahedron; vol. 71; 3; (2015); p. 445 – 450;,
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Synthetic Route of 7252-83-7, A common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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.

[0252] Part A: A suspension of 3-bromothiophenol (15.2 g, 81 mmol), bromoacetaldehyde dimethylacetal (9.5 mL, 81 mmol) and potassium carbonate (12.2 g, 88 mmol) in acetone (90 mL) was stirred at ambient temperature overnight. The solid was filtered and rinsed with ether. Evaporation of the filtrate afforded 23 g of 1-bromo-3-((2,2-dimethoxyethyl)thio)benzene which was carried forward without further purification.

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; O’Connor, Stephen P.; Lawrence, Michael; Shi, Yan; Stein, Philip D.; US2004/186134; (2004); A1;,
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Related Products of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

26.0 g (111 mmol) of the intermediate (A-5), 22.5 g (139 mmol) of (dimethylamino)acetaldehyde diethylacetal, and 50 ml of acetic acid were loaded and the mixture was stirred for 16 hr while being heated at 140C. The reaction solution was cooled to room temperature and then the solvent was removed by evaporation under reduced pressure. The resultant residue was purified by silica gel column chromatography to give 15.9 g (61.8 mmol, yield: 55 mol%) of an intermediate (A-6). APCI-TOFMS, m/z 257 [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 2,2-Diethoxy-N,N-dimethylethanamine, its application will become more common.

Reference:
Patent; Nippon Steel & Sumikin Chemical Co., Ltd.; ISHIYAMA, Takaya; HAYASHIDA, Hiroyuki; SAKAI, Mitsuru; NIINA, Masashi; SHIRAISHI, Kazuto; YOSHIMURA, Kazuaki; EP2687530; (2014); A1;,
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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. 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: ethers-buliding-blocks

EXAMPLE 23 2-Fluoro-6-?(3[-methyl-5-methoxyphenyl)thio]benzonitrile A solution of 1 g (0.005 mol) of 3-bromo-5-methoxytoluene in 10 mL of freshly distilled THF was cooled in dry ice/acetone and stirred under a N2 atmosphere. To this was added dropwise via a syringe 8.46 mL (0.011 mol) of sec-BuLi (1.3M in cyclohexane). The resultant mixture was stirred for 10 min after which 0.19 g of elemental sulfur was added in one portion. The reaction mixture was brought to room temperature and left stirring for 12 h. The mixture was cooled in ice/water bath. 0.69 g (0.005 mol) of 2,6-difluorobenzonitrile in 5 mL of dry DMSO was added. After sitting for 20 min, the mixture was poured into water (100 mL) and extracted with 3*50 mL of EtOAc. The EtOAc solution was washed with 1N NaOH, water, and dried over MgSO4 Removal of EtOAc under vacuo resulted in a crude product which was chromatographed on silica gel (flash; EtOAc/Hexane 1:9). This resulted in 0.63 g (46%) of 2-fluoro-6-[(3-methyl-5-methoxyphenyl)thio]benzonitrile: mp 94-95 C.; NMR (Me2 SO-d6, 200 MHz) delta 2.28 (s, 3H), 3.7 (s, 3H), 6.8-7 (m, 4H), 7.34 (apparent d, 1H), 7.62 (dd, 1H). Anal. Calc. for C15 H12 NOSF: C, 65.92; H, 4.43; N, 5.12; S, 11.73. Found: C, 66.03; H, 4.49; N, 5.09; S, 11.8.

The synthetic route of 29578-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Wellcome Inc.; US5723452; (1998); A;,
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Reference of 150-78-7, 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 150-78-7 as follows.

[00328] FIG. 33 illustrates the synthetic pathway to create DPB A-TPE. [00329] To demonstrate the potential of AIE dots for cellular and mitochondria dual targeted image-guided PDT, we synthesized a new AIEgen, DPBA-TPE (FIG. 33). 3,3′-(2,5- Dimethoxy-l,4-phenylene)bis(2-(4-bromophenyl)acrylonitrile) (5) was prepared by Knoevenagel reaction from 2,5-dimethoxybenzene-l ,4-dicarboxaldehyde (3) and bromophenylacetonitrile (4) under basic conditions. The final product was obtained with satisfactory yields by intermediate (5) and aryl amine (10) in the presence of palladium catalyst under basic conditions.

According to the analysis of related databases, 150-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATIONAL UNIVERSITY OF SINGAPORE; THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY; LIU, Bin; YUAN, Youyong; FENG, Guangxue; TANG, Ben Zhong; QIN, Wei; ZHANG, Chongjing; XU, Shidang; WO2015/163817; (2015); A1;,
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Related Products of 4179-19-5, These common heterocyclic compound, 4179-19-5, name is 3,5-Dimethoxytoluene, 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.

3,5-Dimethoxytoluene (2.93 ml_, 20 mmol) and 4-phenylbutylbromide (4.13 ml_, 1.2 mmol) were reacted as described under General Procedure H and the crude product was purified by flash chromatography (silica-gel, petroleum ether/EtOAc 200:1) to afford the product as a clear oil (4.6 g, 81%). 1H NMR (300 MHz, CDCI3) delta 7.13-7.22 (m, 5H), 6.34 (s, 2H), 3.76 (s, 6H), 2.60-2.64 (m, 4H), 2.31 (s, 3H), 1.53-1.67 (m, 4H).; General Procedure H: Alkylation of 3,5-dimethoxytoluene A solution of n-butyllithium in hexanes (1.7 M, 1.2 eq.) was added over 0.25 h to a solution of 3,5-dimethoxytoluene (1.0 eq.) in THF (1 M) at 0 0C. The reaction mixture was stirred at 0 0C for 1 h then at room temperature for 3 h. The reaction was cooled to 0 0C and a solution of the alkyl bromide (1.2 eq.) in toluene (2 M) was added over 0.1 h. The reaction mixture was allowed to warm to room temperature and heated to 80 0C for 3-4 h. The reaction was quenched slowly with water and partitioned over EtOAc and water. The phases were separated and the aqueous phase was extracted twice with EtOAc. The pooled organics were washed with brine, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography.

The synthetic route of 4179-19-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIONOMICS LIMITED; WO2009/43117; (2009); A1;,
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