Author: Jessica.F

Reference of 366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-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.

Cyclopentanone (16.8 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford N-Cyclopentyl-3-fluoro-4-methoxyaniline (2.0 g, 48percent yield). MS m/z=210 [M+H].

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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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. Quality Control of 1,4-Dimethoxybenzene

General procedure: To a stirred solution of starting compound (0.5-1.2 mmol) in DMF-H2O (95:5, v/v, 8-12 mL) mixture was added NBS (4.0-4.2 mmol) at room temperature. The contents were stirred at room temperature about 10 min and then heated for appropriate duration mentioned in Table 2. Progress of the reaction in every case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with aqueous NaHCO3 (20%, 20-30 mL) solution. The insoluble precipitate was isolated by filtration and dried in vacuo. It was further purified by either recrystallization with ethyl acetate/n-hexane mixture or short pad silica gel column chromatography led to pure product.

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:
Article; Natarajan, Palani; Vagicherla, Vinuta Devi; Vijayan, Muthana Thevar; Tetrahedron Letters; vol. 55; 24; (2014); p. 3511 – 3515;,
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Some common heterocyclic compound, 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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. Formula: C7H6BrFO

Refined Mg turnings (593 mg, 24.4 mmol) were suspended in dry THF (10 mE). 5-bromo-2-fluoroanisole (1 g, 4.877 mmol) and 1, 2-dibromoethane (500 mg, 2.66 mmol) were dissolved in dry THF (10 mE). The above solution was added to the Mg suspension at room temperature (25 C.) without cooling. After the addition, the reaction was heated to a slight reflux with a heat gun. The reaction was initiated and maintained at reflux for another 0.5 h. An aliquot was quenched with acetone and TEC (petroleum ether) showed most of the starting material was consumed. The mixture of compound E-2 (.-M.244 M in THF) was used in the next step directly.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103291-07-2, its application will become more common.

Reference:
Patent; Pfizer Inc.; Tatlock, John Howard; McAlpine, Indrawan James; Tran-Dube, Michelle Bich; Rui, Eugene Yuanjin; Wythes, Martin James; Kumpf, Robert Arnold; McTigue, Michele Ann; (181 pag.)US2016/244475; (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. 111-95-5, name is Bis(2-methoxyethyl)amine, A new synthetic method of this compound is introduced below., Formula: C6H15NO2

Compound 1-3 (3.5 g, 13.5 mmol) was dissolved in 1,4-dioxane (50 mL), followed by addition of compound 5-1 (1.9 g, 14.2 mmol), and potassium carbonate (3.7 g, 27 mmol) was added under stirring in batches, followed by stirring the reaction overnight at 70 C., TLC monitoring showed that the starting material 1-3 was completely reacted. The solvent was removed under reduced pressure to obtain a concentrated residue. The concentrated residue was dispensed with dichloromethane (20 mL), an appropriate amount of silica gel was added and the sample was stirred, spin-dried under reduced pressure and directly placed on a silica gel column for column chromatographic purification, with an eluent (dichloromethane:methanol=20/1-5/1) to obtain the target product as a pale yellow oil 5-2 (1.2 g, 40%), LC-MS: m/z=222[M+H]+.

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; Shenzhen China Resources Gosun Pharmaceutical Co., Ltd.; Jiang, Xiongjie; Huang, Quanhua; Yang, Zhanao; (43 pag.)US2017/2028; (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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, A new synthetic method of this compound is introduced below., Computed Properties of C9H13NO2

General procedure: In a simply obtainable screw cap bottle, a mixture of ethylcyanoacetate6 (1.2 mmol) and the suitable amine (1 mmol) in EtOH (10 mL)was stirred at RT for 4-8 h. After completion as indicated by TLC, thereaction liquid was refrigerated down to 4 C in an ice bath. In severalcases, the precipitation of amide usually took later than some minutesto hours [12]. Filtered off the formed solid, rinsed with ether numeroustimes to obtain pure 7(a-q) in corresponding 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:
Article; Shaik, Jeelan Basha; Yeggoni, Daniel Pushparaju; Kandrakonda, Yelamanda Rao; Penumala, Mohan; Zinka, Raveendra Babu; Kotapati, Kasi Viswanath; Darla, Mark Manidhar; Ampasala, Dinakara Rao; Subramanyam, Rajagopal; Amooru, Damu Gangaiah; Bioorganic Chemistry; vol. 88; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 143-24-8, name is 2,5,8,11,14-Pentaoxapentadecane, 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 143-24-8, Recommanded Product: 143-24-8

(a) 7-Benzyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]-azepine hydrochloride 10.9 gm (30 mmols) of 1-benzyl-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)-azepine were dissolved in a mixture of 20 ml ethylenediamine and 30 ml tetraethyleneglycol dimethyl ether, and air was passed through the solution at 120 C. for eight hours. Thereafter, the reaction mixture was poured into water, and the aqueous composition was extracted with chloroform. The chloroform extract solution was dried and evaporated, and the residue was chromatographically purified on silicagel with methanol as the mobile phase. Subsequently, the hydrochloride was precipitated from ethanol with ethanolic hydrochloric acid. Yield: 2.4 gm (29% of theory) Melting point: 244-247 C. Calculated: C: 65.33%; H: 6.58%; N: 15.24%; Cl: 12.85% Found: C: 65.01%; H: 6.42%; N: 14.89%; Cl: 12.31%.

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, 2,5,8,11,14-Pentaoxapentadecane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4409220; (1983); A;,
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Synthetic Route of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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 , 1-Di-te/f-butoxy-A/,A/-dimethylmethanamine (6.77 ml, 28.3 mmol) was added to a suspension of 2-({[(benzyloxy)carbonyl]amino}methyl)-1-ethyl-1 /-/-1 ,3-benzodiazole-6- carboxylic acid, Intermediate 80 (2.50 g, 7.08 mmol) in alpha,alpha,alpha-trifluorotoluene (50 ml). The reaction mixture was heated at 100 C for 1 h. The reaction mixture was allowed to cool to RT then 1 , 1-di-te/f-butoxy-A/,A/-dimethylmethanamine (6.77 ml, 28.3 mmol) was added dropwise over 15 min. The resultant mixture was heated at 100 C for 45 min. The reaction mixture was cooled to 50 C then 1 , 1-di-te/f-butoxy-A/,A/-dimethylmethanamine (3.38 ml, 14.15 mmol) was added dropwise over 5 min. The resultant mixture was heated at 100C for 0.5 h then allowed to cool to RT. The reaction mixture was partitioned between EtOAc (50 ml) and water (50 ml). The phases were separated then the organic phase was washed with water (2 x 30 ml), saturated aqueous NaHCC solution (20 ml) and brine (10 ml) then dried over Na2S04, filtered and concentrated in vacuo to afford a beige solid (2.5 g). The solid thus obtained was suspended in MeCN (10 ml). The solid was collected by filtration then dried under vacuum to afford the product as an off-white solid (2.30 g, 79%). 1 H NMR (500 MHz, DMSO-cfe) delta 8.07 (s, 1 H), 7.97 (m, 1 H), 7.76 (dd, J = 8.4, 1.5 Hz, 1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.34 (m, 5H), 5.07 (s, 2H), 4.55 (d, J = 6.0 Hz, 2H), 4.38 – 4.25 (m, 2H), 1.57 (s, 9H), 1.29 (m, 3H). LC/MS (System A): m/z (ESI+) = 410 [MH+], Rt = 1.17 min, UV purity = 99%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
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Reference of 17715-69-4, A common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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 thermometer, a stirrer, a reflux condenser attached to the flask, and subjected to nitrogen gas purging, 1-bromo-2,4-dimethoxybenzene 110g, 257g IPA, and potassium carbonate added to the solution previously prepared by dissolving 139g to 107g water and the reaction vessel was stirred while nitrogen It is replaced, and then tetrakistriphenylphosphine palladium (0), adding to 5.9g, also 4-methoxy-phenylboronic acid to pre-IPA 109g 83g Solution was added dropwise to the dissolved. After 3 hours the reaction mixture was heated to reflux, added 500mL of water, separate the IPA layer, the water layer was Transferred to a separatory funnel, the toluene extract was added 500mL. An organic layer was washed with saturated sodium chloride solution each. Solvents in vacuo After distilling off the one, added 500mL of toluene, and the precipitate was separated by filtration, toluene was distilled off under reduced pressure. Methane to the obtained crude product Adding to come 200mL, taking over the precipitate, and dried 5 hours in a vacuum dryer of 50 , 2,4,4′- tree fertilization methoxy phenyl Gained 105g

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; Dainippon Inc. & Chemicals; Yoshimoto, Yasuyo; Morinika, Kunihiro; Kinoshita, Hiroshi; (17 pag.)KR2016/8529; (2016); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., name: 4-(Difluoromethoxy)aniline

In tetrahydrofuran (10 ml) was dissolved 4-difluoromethoxyaniline (1 .0 g 6.29 mmol). To this, pyridine (1 .0 ml, 12.58 mmol) and methane sulfonyl chloride (0.7 ml, 9.43 mmol) were added at 0-5 C and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water and brine solution. Organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product (1 .5 g) was used as such for next step. 1 H-NMR(400MHz,DMSO-d6)delta: 2.97(s,3H),7.16(d,J=8.8Hz,2H),7.16(t,J=7.4Hz, 1 H), 7.24 (d,J=9.2Hz,2H),9.77(s,1 H).

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; KATOCH, Rita; INAGAKI, Hiroaki; FUJISAWA, Tetsunori; WO2014/24056; (2014); A1;,
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Reference of 5905-69-1, A common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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.

To a stirred solution of bromophenol derivative AM (2.0 g, 8.97 mmol) in 1,4-dioxane (40 mL) were added bis(pinacolato)diboron (2.28 g, 8.97 mmol) and KOAc (2.64 g, 26.90 mmol) at RT under inert atmosphere, and the mixture was degassed for 20 min by purging with argon. To this solution, Pd(dppf)2Cl2 (0.33 g, 0.45 mmol) was added, and the mixture was degassed for a further 10 min. The reaction mixture was then heated to 80 C. and stirred for 3 h at this temperature. Progress of the reaction was monitored by TLC. The reaction mixture was then cooled to RT and diluted with EtOAc (30 mL). The resultant solution was filtered through a Celite pad, and the filtrate was then concentrated in vacuo. The crude compound was purified by silica gel column chromatography (eluting with 5-10% EtOAc gradient in hexanes) to afford AN (1.72 g, 6.37 mmol, 71%). 1H NMR (500 MHz, CDCl3): delta 7.81 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.5 Hz, 2H), 6.54 (t, JF-H=74.0 Hz, 1H), 1.34 (s, 12H).

The synthetic route of 5905-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
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