Month: July 2021

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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 366-99-4

General procedure: To a solution of compound 12 (bakuchiol-o-triflate) (1 mmol) in toluene (10 mL M), amine (3.0 mmol), Cs2CO3 (4.0 mmol), ligand (±) BINAP (0.6 mol) and Pd(OAc)2 (0.2 mol) were added under an inert atmosphere. The reaction mixture was degassed at RT and refluxed (120 °C) for 24 hr. Then, the reaction mixture was brought to RT, diluted with EtOAc and filtered through celite. To the reaction mixture, brine (20 mL) was added and extracted with EtOAc (2 × 10 mL). The combined organic layerwas dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the product after silicagel chromatography purification (Hex/EtOAc, 9.5:0.5).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 366-99-4.

Reference:
Article; Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 75 – 80;,
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Application of 7252-83-7, 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 7252-83-7 as follows.

Step 1: Methyl 2-bromo-3-cyclohexyl-l-(2.2-dimethoxyethyl)-lH-indole-6-carboxylate; To a stirred solution of methyl 2-bromo-3-cyclohexyl-lH-indole-6-carboxylate (prepared as described in published International patent application WO2004/087714) (0.2 M, 1 eq.) in DMF at RT was added NaH (60 % dispersion in mineral oil, 1.75 eq). After Ih, KI (8 mol %) and bromoacetaldehyde dimethyl acetal (2.5 eq) were added and the reaction heated at 80 0C for 17 h. After cooling to RT, the reaction was quenched by addition of aqueous HCl (IN) and extracted into EtOAc (x3). The combined organics were washed with HCl (IN), H2O and brine before being dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (Biotage, 5-10 % EtOAc/PE gradient) gave the title compound as a white solid (79 %); MS (ES+) m/z 446 (M+H)+, 448 (M+H)+.

According to the analysis of related databases, 7252-83-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); A2;,
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29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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. name: 1-Bromo-3-methoxy-5-methylbenzene

A. Cu(l)l (0.05 g, 0.25 mmol) and Nal (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 mi Anhydrous dioxane (5 mL), N,N-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and 1-bromo-3-methoxy-5-methylbenzene (Compound No. 24, 1.0 g, 5 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110C in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2CI2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (Compound No. 25, 1.05 g, 87% yield) as a pale yellow oil.

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

Reference:
Patent; AQUINOX PHARMACEUTICALS INC.; MACKENZIE, Lyoyd, F.; MACRURY, Thomas, B.; HARWIG, Curtis; BOGUCKI, David; RAYMOND, Jeffery, R.; PETTIGREW, Jeremy, D.; KHLEBNIKOV, Vladimir; SHAN, Rudong; WO2014/110036; (2014); A1;,
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Application of 1462-37-9, 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Under an argon atmosphere,methyl 2-(4-hydroxyphenyl)acetate (3.51 g, 21.14 mmol) and caesium carbonate (13.78 g, 42.28 mmol)were suspended in dimethylformamide (130 mL), the mixture was stirred at ambient temperaturefor 2 h. Benzyl-2-bromoethylether (5.00 g, 23.25 mmol) was added and it was stirred at ambienttemperature for further 12 h. Water (250 mL) and ethyl acetate (250 mL) were added and the resultingphases separated. The organic phase was dried over sodium sulfate and concentrated in vacuum.Purification by chromatography on silica gel (gradient: 0?100percent ethyl acetate in cyclohexane) affordedthe title compound 8a as a white solid (5.30 g, 84percent yield): 1H-NMR (DMSO-d6): delta = 7.38?7.26 (m, 5H),7.19?7.15 (m, 2H), 6.92?6.88 (m, 2H), 4.55 (s, 2H), 4.13?4.10 (m, 2H), 3.78?3.74 (m, 2H), 3.60 (s, 3H), 3.59(s, 2H) ppm. 13C-NMR (DMSO-d6): delta = 172.33, 157.88, 138.78, 130.83, 128.70, 127.99, 127.89, 126.83,114.83, 72.55, 68.71, 67.53, 52.06, 39.72 ppm. MS (m/z): 301 [M + H]+.

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

Reference:
Article; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
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Related Products of 910251-11-5, A common heterocyclic compound, 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, molecular formula is C2H5BF3KO, 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.

j0288j Combined 3 -chloro-6-(4-(2,4-difluorophenoxy)piperidin- l-yl)-5-(isopropylamino)pyrazine-2-carbonitrile (50 mg, 0.123 mmol), PdC12(dppf) (8.97 mg, 0.0 12 mmol), potassium methoxymethyltrifluoroborate (74.5 mg, 0.490 mmol) and 2N Na2CO3 (0.5 ml) in dioxane (1.0 mL). The reaction mixture was heated in a microwave at 130 C for 30 mm. The reaction mixture was filtered and purified by HPLC using Method A twice to afford the title compound as its TFA salt (6 mg, 10%) as a yellow film. 1H NMR (500 MHz, methanol-d4) ppm 1.27 (d, J=6.35 Hz, 6 H) 1.87 – 2.04 (m, 2 H) 2.08 – 2.20 (m, 2 H) 3.05 (ddd, J=12.45, 8.54, 3.42 Hz, 2 H) 3.37 – 3.50 (m, 2 H) 4.28 – 4.41 (m, 1 H) 4.43 – 4.53 (m, 3 H) 6.80 – 6.93 (m, 1 H) 6.98 (ddd, J=11.35, 8.66, 2.93 Hz, 1 H) 7.17 (td, J=9.28, 5.37 Hz, 1 H) ; ESI-MS mlz [M+H]+ 418.4.

The synthetic route of 910251-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; ADAMS, Mark E.; BROWN, Jason W.; HITCHCOCK, Stephen; HOPKINS, Maria; KIKUCHI, Shota; LAM, Betty; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; WO2015/123533; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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 102-52-3, Safety of 1,1,3,3-Tetramethoxypropane

1,1,3,3-Tetramethoxypropan (0.16 g, 1.0 mmol) was added dropwise to a stirred solution of 4-hydrazinyl-6-methyl-2-(pyridin-2-yl)pyrimidine (0.20 g, 1.0 mmol) in a mixture of water (2 ml) and concentrated HCl acid (0.4 ml) at 40 C. The reaction mixture was stirred for 1 h, cooled down, diluted with CHCl3 and washed with the saturated solution of NaHCO3, then with water, and dried over MgSO4. After CDCl3 removal under reduced pressure the residue crystallized. Yield: 0.18 g (75%), m.p. 97 C (from hexane). Anal. Calc. for C13H11N5: C, 65.77; H, 4.62; N, 29.56. Found: C, 65.82; H, 4.64; N, 29.54%. 1H NMR (CDCl3, 300.15 MHz) delta (ppm): 8.85 (ddd, 1H, J = 4.7, 1.8, 1.0 Hz, 6-Hpyridine), 8.76 (dd, 1H, J = 2.7, 0.4 Hz, 5-Hpyrazole), 8.52 (dt, 1H, J = 7.7, 1.0 Hz, 3-Hpyridine), 7.86 (dt, 1H, J = 7.7, 1.8 Hz, 4-Hpyridine), 7.79 (s, 1H, 5-Hpyrimidine), 7.80-7,78 (m, 1H, 3-Hpyrazole), 7.40 (ddd, 1H, J = 7.7, 4.7, 1.0 Hz, 5-Hpyridine), 6.51 (dd, 1H, J = 2.7, 1.6 Hz, 4-Hpyrazole), 2.72 (s, 3H, Me). IR (KBr pellet, nu cm-1): 3161w, 3130w, 3076m, 3055w, 3008w, 2918w, 1587vs, 1560vs, 1523s, 1458vs, 1441s, 1394s, 1379s, 1225m, 1149w, 1115w, 1037m, 985w, 951m, 914m, 862m, 810m, 760s, 740m, 679w, 604m, 584w.

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, 1,1,3,3-Tetramethoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bushuev, Mark B.; Gatilov, Yuri V.; Nikolaenkova, Elena B.; Vasiliev, Vladimir G.; Krivopalov, Viktor P.; Inorganica Chimica Acta; vol. 395; (2013); p. 95 – 103;,
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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. SDS of cas: 2393-23-9

1-methyl-1H-imidazole-2-carbaldehyde (0.882 g, 8.019 mmol, 1.1 equiv) and (4-methoxyphenyl)methanamine (0.943mL, 7.29 mmol, 1 equiv) were added to a 250 mL round bottom flask containing activatedmolecular sieves in methanol (73 mL). Reaction mixture was stirred at room temperature (RT).After completion of reaction (3 h), as monitored by TLC, reaction mixture was cooled to 0oC,followed by the addition of sodium borohydride. After complete consumption of imine (17 h), asmonitored by TLC, reaction was quenched with water (25 ml) followed by filtration of molecularsieves, evaporation of methanol in-vacuo, and extraction with ethyl acetate (25 ml X 5). Thecombined organic layers were dried over anhydrous Na2SO4, decanted, followed by removal ofvolatiles in-vacuo. Crude mixture was purified by flash column chromatography using 25-100%EtOAc in hexanes providing 10a (1.27 g, 76%) as a yellow oil

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:
Article; Joshi, Madhur S.; Lansakara, Ashabha I.; Pigge, F. Christopher; Tetrahedron Letters; vol. 56; 23; (2015); p. 3204 – 3207;,
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2688-84-8, name is 2-Phenoxyaniline, 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. Application In Synthesis of 2-Phenoxyaniline

General procedure: 4-phenoxyphenol (186mg, 1mmol) was stirred with TEA (278muL, 2mmol) in Anhydrous DCM (10mL) at 0C, then 2-Chloroethanesulfonyl chloride (105muL, 1mmol) which was diluted with DCM (2mL) was slowly added into the mixture. The reaction mixture was stirred for 2h then evaporated. The residue was diluted and extracted with EtOAc then washed with water for 3 times. The organic layers were dried over Na2SO4 and evaporated. The residue was chromatographed (silicagel, Petroleum ether/EtOAc=3:1) to give 4-phenoxyphenyl ethenesulfonate (DC-TEADin03) (193mg, 70%) as a colorless oil.

The synthetic route of 2688-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Wenchao; Wang, Jun; Li, Yong; Tao, Hongru; Xiong, Huan; Lian, Fulin; Gao, Jing; Ma, Hongna; Lu, Tian; Zhang, Dan; Ye, Xiaoqing; Ding, Hong; Yue, Liyan; Zhang, Yuanyuan; Tang, Huanyu; Zhang, Naixia; Yang, Yaxi; Jiang, Hualiang; Chen, Kaixian; Zhou, Bing; Luo, Cheng; European Journal of Medicinal Chemistry; vol. 184; (2019);,
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Electric Literature of 19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

PPTS (38.3 g, 152 mmol) was added to a solution of the product from Step 1 (31.3 g, 152 mmol) and 4-bromo-3-methoxyaniline (28 g, 139 mmol) in DCM (700 mL). The mixture was heated to reflux and stirred for 20 h. The mixture was cooled, and the solids were removed by filtration and washed with DCM. The filtrate was concentrated and purified on silica gel (gradient elution 10percent to 50percent DCM in hexanes) to give the title compound (49 g, 94percent yield). LRMS (M+H)+ Calcd.: 376.0; found 376.2.

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, 4-Bromo-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; MSD Italia S.r.l.; MCCAULEY, John, A.; LIVERTON, Nigel, J.; HARPER, Steven; MCINTYRE, Charles, A.; RUDD, Michael, T.; (73 pag.)EP2268285; (2018); B1;,
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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. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 14804-31-0

n-Butyllithium (2.5 M in hexanes, 60 mL, 150.0 mmol) was added dropwise to a solution of 4-bromo-1-methoxy-2-methylbenzene (27.78 g, 138.2 mmol) in THF (300 mL) at-78 C. The mixture was stirred at -78 C for 1 h and then added dropwise to a solution of ethyl 4-oxocyclohexanecarboxylate (22.34 g, 131.3 mmol) in THF (300 mL) at -78 C. The mixture was stirred at -78 C for 2 h, added to sat?d NH4C1 (600 mL) and then extracted with EtOAc (2×600 mL). The combined organic extracts were washed with water (400 mL), washed with brine (400 mL), dried (Na2504), filtered, concentrated, and purified by silica gel chromatography (petroleum ether/EtOAc = 10/1) to give ethyl 4-hydroxy-4-(4-methoxy-3 – methylphenyl)cyclohexanecarboxylate (18.9 g, 45%) as a yellow oil. ?H NIVIR (400 MHz, DMSO): 7.11-7.26 (m, 2H), 6.75-6.84 (m, 1H), 4.59-4.64 (m, 1H), 3.98-4.11 (m, 2H), 3.72 (s, 3H), 2.25-2.39 (m, 1H), 2.07-2.13 (s, 3H), 1.77-1.93 (m, 3H), 1.42-1.75 (m, 5H), 1.11- 1.23 (m, 3H); LCMS: 275.2 [M-OH].

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (169 pag.)WO2018/170166; (2018); A1;,
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