Month: May 2021

Application of 54314-84-0, 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. 54314-84-0 name is ((3-Bromopropoxy)methyl)benzene, 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.

Synthesized according to the methods of general procedure 4 in U.S. Pat. Pub. No. 20090227541 (U.S. Pat. App. No. 12/142,692) using the following reactants and amounts: 2-bromo-3-hydroxy-4-methoxy-benzaldehyde (1.0 g, 4.32 mmol), (3- bromo-propoxymethyl)-benzene (0.76 mL, 4.32 mmol), cesium carbonate (2.11 g, 6.5 mmol), DMF (30 mL). Purification: flash chromatography (10percent EtOAc/hexanes): yield 1.54 g (95percent). 1H NMR (400 MHz, CDC13) delta (ppm): 10.26 (s, 1 H), 7.73 (d, J=8.6 Hz, 1 H), 7.46-7.18 (m, 5 H), 6.95 (d, J=8.6 Hz, 1 H), 4.56 (s, 2 H), 4.14 (t, J=6.1 Hz, 2 H), 3.92 (s, 3 H), 3.77 (t, J=6.2 Hz, 2 H), 2.15 (quin, J=6.5 Hz, 2 H); MS (ESI): m/z = 381 (M+l, positive).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, ((3-Bromopropoxy)methyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; DING, Charles; PLATTNER, Jacob, J.; ALLEY, Michael Richard, Kevin; ROCK, Fernando; ZHANG, Suoming; EASOM, Eric; LI, Xianfeng; ZHOU, Ding; WO2012/33858; (2012); A2;,
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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 1515-95-3 as follows. name: 1-Ethyl-4-methoxybenzene

General procedure: A stock solution of CuCl2·2H2O in water (0.0171 g/mL) was prepared (by dissolving 0.171 g in 10 mL H2O). To a Teflon screw cap glass tube, catalyst A (100 muL of a stock solution, 0.01 mmol of CuCl2, 2.1mg, 0.01 mmol of neocuproine) was added. Then 0.7 mL of H2O, 0.2 mmol of arylalkanes, and 70 % aq tert-butyl hydroperoxide (200 muL, 1.4 mmol) were added in each case. The mixture was stirred vigorously at room temperature till to its reaction time specified in the Tables 2 and 3. The reaction mixture was then diluted with ethyl acetate and the products dissolved in ethyl acetate layer were analyzed by GC using internal standard 1,4-di-tert-butylbenzene (19.4 mg, 0.1 mol). For product separation, the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined extracts were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated and product isolation was carried out by TLC. The pure products of benzophenone, 9-fluorenone (Table 2, entries 2 and 3) and 4-methoxyacetophenone (Table 3 entry 2) were obtained from drying their ethyl acetate extract without chromatographic workup. Filtration of the reaction mixture afforded pure 9-xanthenone (Table 2, entry 4).

According to the analysis of related databases, 1515-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hossain, Md. Munkir; Shyu, Shin-Guang; Tetrahedron; vol. 72; 29; (2016); p. 4252 – 4257;,
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Adding a certain compound to certain chemical reactions, such as: 583-19-7, name is 1-Bromo-2-ethoxybenzene, 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 583-19-7, Application In Synthesis of 1-Bromo-2-ethoxybenzene

Synthesis of Compound 67.2. [0740] Into a 100-mL 3-necked round-bottom flask was placed Mg (1.55 g) and 10 mL of tetrahydrofuran. Then 1-bromo-2-ethoxybenzene (1 g) and 1,2-dibromoethane (100 mg, 0.53 mmol, 0.01 equiv) were added to initiate the reaction. Then a second batch of 1-bromo-2-ethoxybenzene (9 g) were dissolved in 40 mL THF was added dropwise. The resulting solution was stirred for 2 h at room temperature. The mixture was directly used in the next step.

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-2-ethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nimbus Apollo, Inc.; Harriman, Geraldine C.; Masse, Craig E.; Harwood, James; Bhat, Sathesh; Greenwood, Jeremy Robert; US2013/123231; (2013); 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. 20059-73-8, name is 2-(4-(Aminomethyl)phenoxy)-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., SDS of cas: 20059-73-8

Table HH: Examples of amides prepared from 3-(2-chlorophenyl)isoxazoIe-5-carboxyIic acid; A 20 mL scintillation vial is charged with a solution of 3-(2-chlorophenyl)isoxazole-5- carboxylic acid in DMF (1.0 eq, 6.96 mmol, 35.31 mg), a solution of HATU in DMF (1.20 eq, 8.84 mmol), a solution of pre-weighed 0.6 mmol amine monomer in DMF(1.30 eq, 3.0 mL DMF), and a solution of N, N-diisopropylamine in DMF (2.0 eq, 14.74 mmol). The vial was capped and placed in a heater/shaker at 90 0C overnight. The mixture is then passed through a solid phase extraction column with silica carbonate medium using MeOH. The solvent was removed and the crude material was purified by HPLC method (n) and the solvents evaporated.

The synthetic route of 20059-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/11850; (2009); A2;,
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Related Products of 60792-79-2, A common heterocyclic compound, 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, molecular formula is C4H14Cl2N2O, 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.

Example 6 Preparation of N-(2-(2-(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenamidoethoxy)ethyl)-5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2-carboxamide (I-3) In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate (850 mg, 74%).

The synthetic route of 60792-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82202; (2011); 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. 62257-15-2, name is 2-Fluoro-5-methoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Fluoro-5-methoxyaniline

Compound 36 (1eq.) Was dissolved in acetone was added KOH (4eq.), Was added with stirring dimethyl sulfate (1.5eq.), The reaction was stirred for 1 hour, then added 1ml of water and stirred for 1.5h. After completion of the reaction with ethyl acetate, dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography to give intermediate 37.Intermediate 37 (1eq.) Was dissolved in glacial acetic acid, and then the acrylic acid (2eq.) Was added dropwise, with stirring was added 98% sulfuric acid (0.1eq.), 80 heated 5h. After completion of the reaction, saturated sodium bicarbonate solution and extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography to give intermediate 38.Intermediate 38 (1mmol) was dissolved in 6mlEaton’s reagent, and the reaction was heated to 65 deg.] C overnight. After completion of the reaction with sodium hydroxide solution and extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography to give intermediate 39.Compound 39 (1eq.) Was dissolved in anhydrous dichloromethane, the reaction flask was replaced with argon, -78 deg.] C was added BBr3 (5eq.), Gradually warmed to room temperature, the reaction for 5h, quenched with saturated sodium bicarbonate solution and neutralized, extracted with ethyl acetate, the organic phase was dried, purified by silica gel column chromatography to give intermediate 40.Compound 40 (1eq.) Was dissolved in acetone, was added Cs2CO3 (6eq.), Chloromethyl methyl ether was added to the strict (3eq.) The reaction flask under a nitrogen atmosphere with ice bath, the temperature was raised to 10 , the reaction 2h. After completion of the reaction and the reaction with 2N hydrochloric acid, extracted with ethyl acetate, and purified by silica gel column chromatography, the organic phase was dried, to give intermediate 41.Compound 41 was dissolved in anhydrous tetrahydrofuran, -40 deg.] C was added LDA (2eq.), Half an hour later butyryl chloride (1.1eq.), And the reaction warmed to room temperature, the reaction 0.5h, water was added to quench the reaction, under reduced pressure spin down tetrahydrofuran, extracted with ethyl acetate, the organic phase was dried after pressing down spin solvent, the crude product is dissolved in ethanol was added hydrazine hydrate (3eq.), 60 reaction 2h. After completion of the reaction was purified by silica gel chromatography to give intermediate 42 by column.Compound 42 (1eq.) Was added to trifluoroacetic acid, stirred at room temperature 1h, after completion of the reaction, the solvent under reduced pressure to spin dry, and the crude product was purified by silica gel column chromatography to give the desired product 43.Compound 43 was dissolved in dry tetrahydrofuran, was added sodium borohydride (5 eq.), Stirred at room temperature 3h, after completion of the reaction, water was added to quench the reaction, under reduced pressure of tetrahydrofuran spin down, extracted with ethyl acetate, dried over anhydrous magnesium sulfate purification by silica gel column chromatography to give compound KQ77.

The synthetic route of 62257-15-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsinghua University; He, Wei; Ruan, Ke; (60 pag.)CN105523955; (2016); A;,
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Reference of 19500-02-8, The chemical industry reduces the impact on the environment during synthesis 19500-02-8, name is 3-Methoxy-2-methylaniline, I believe this compound will play a more active role in future production and life.

Reference Production Example 4 (0589) A mixture of 15.0 g of 3-amino-1-methoxy-2-methylbenzene, 48.7 g of triphosgene, and 350 ml of toluene was stirred with heating under reflux for 3 hours. The reaction mixture allowed to cool was concentrated under reduced pressure to obtain 17.0 g of 1-methoxy-3-isocyanato-2-methylbenzene (hereinafter referred to as 4A). (0590) 1H-NMR (CDCl3) delta (ppm): 2.19 (3H, s), 3.82 (3H, s), 6.69 (1H, d, J=8.2 Hz), 6.72 (1H, dd, J=0.5, 8.0 Hz), 7.09 (1H, t, J=8.2 Hz).

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, 3-Methoxy-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; SHIODA, Takayuki; ARIMORI, Sadayuki; (191 pag.)US2016/157489; (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. 136-90-3, name is 4-Methoxy-3-methylphenylamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H11NO

To a solution of 4-methoxy-3-methyl aniline (8 g, 58.39 mmol) in THF (100 mL), maintained at 0C, was added pyridine (5.8 mL, 72.98 mmol), followed by phenyl chloroformate (7.2 mL, 58.39 mmol). The reaction mixture was stirred at r.t. for 2 h, then quenched with water (50 mL) and extracted with EtOAc (2 x 100 mL). The organic layer was separated and washed with water (50 mL), then dried over sodium sulfate and concentrated in vacuo, to afford the title compound (13 g, 86%). deltaEta (CDC13, 400 MHz) 7.45-7.34 (m, 2H), 7.34-7.13 (m, 5H), 6.84 (s, 1H), 3.81 (s, 3H), 2.21 (s, 3H).

The synthetic route of 136-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HORSLEY Helen Tracey; HUANG Qiuya; NEUSS Judi Charlotte; REUBERSON James Thomas; VANDERHOYDONCK Bart; WO2015/193169; A1; (2015);,
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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. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, A new synthetic method of this compound is introduced below., name: 4-(2-Methoxyethoxy)aniline

In a 25 mL three neck RBF with thermometer pocket, a solution of tert-butyl (2-chloro-5-fluoropyrimidin-4-yl)(3-(N-hydroxyacrylamido)phenyl)carbamate (0.250 g) in 1,4-dioxane (8.0 mL) was added. 4-(2-Methoxyethoxy)aniline (0.122 g) was added and the reaction was degassed for 10 minutes under argon. After 10 minutes, Xantphose (0.0176 g) and Cs2CO3 (0.396 g) were added and again degassed the reaction for 10 minutes followed by addition of Pd (OAc)2 (0.003 g) under argon. The reaction was heated to 80 C. and stirred for 3.5 hr under argon. The reaction was monitored on TLC using hexane:ethyl acetate (2:8) as mobile phase. After completion of the reaction, the reaction mixture was allowed to cool at room temperature. The reaction mixture was poured into water and product was extracted with ethyl acetate (3*25 ml). Ethyl acetate layer washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to give 0.250 g of tert-butyl (5-fluoro-2-((4-(2-methoxyethoxyl)phenyl)amino)pyrimidin-4-yl)(3-(N-hydroxyacrylamido)phenyl)carbamate. This crude material was used in the next step without any further purification. M+1=539.9.

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; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2015/174128; (2015); A1;,
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These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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. Safety of 4-Methoxy-N-methylbenzylamine

General procedure: A solution of 24 (1.0 equiv.), HOBt (1.1 equiv.) and EDC (1.5 equiv.) in DMF (1.3 mmol/mL) was stirred at rt for 15 minutes. The appropriate amine (2.0 equiv.) was added and the resulting solution was stirred at rt for 5 hours. Reaction media was diluted with water and aqueous phase was extracted 3 times with EtOAc. Combined organic layers were washed successively with a solution of HCl 1N, a saturated solution of NaHCO3 and brine, dried over Na2SO4 and concentrated. The resulting solid was then purified by column chromatography on silica gel using the appropriate heptanes:EtOAc mixture.

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

Reference:
Article; Bollenbach, Maud; Lugnier, Claire; Kremer, Melanie; Salvat, Eric; Megat, Salim; Bihel, Frederic; Bourguignon, Jean-Jacques; Barrot, Michel; Schmitt, Martine; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 269 – 290;,
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