Month: August 2021

Electric Literature of 262587-05-3, These common heterocyclic compound, 262587-05-3, name is 1-Bromo-3-(difluoromethoxy)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.

93 mg of 1 -bromo-3(dofluoromethoxy)benzene (0.42 mmol; 1.00 eq) and the successively 142 mg of 1 -[3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]azetidine-3-carboxylic acid (preparation 9; 0.42 mmol; 1.00 eq) dissolved in 4 mE of DME, 3.4 mg of Pd(dppf)C12, CH2C12 (0.01 eq.) and finally 127 mg of CsF (0.83 nnol; 2.00 eq) were introduced into a microwave- resistant 10 mE reaction vessel. The reaction mixture was microwave-irradiated for 1 h at 120 C. The reaction medium was then taken up with ethyl acetate and water, while adjusting the pH to 6, and then extracted with ethyl acetate and washed with brine. The organic phase was dried over magnesium suflate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (l3iotage 10 g silica 15-40 jtmlliquid deposit in dichloromethane) using a cyclohexane/0% to 100% dichloromethane gradient. The fractions containing the targeted product were combined and then evaporated, under reduced, pressure to give 99 mg of title compound in the form of a colorless oil,Yld: 33%.10548] ?H NMR (300 MHz, CHC13-d) oeppm 2.24 (s, 3H)3.41-3.49 (m, 1H) 3.62 (s, 3H) 3.92-4.02 (m, 4H) 6.18 (s, 1H) 6.32 (s, 1H) 6.43 (t, J=74 Hz, 1H) 6.68 (s, 1H) 6.93-6.96 (m, 1H) 7.19-7.3 1 (m, 3H).EC-MS mlz (M+H): 348.

The synthetic route of 262587-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 1758-46-9, The chemical industry reduces the impact on the environment during synthesis 1758-46-9, name is 2-Phenoxyethylamine, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of (0.137 g, 1 mmol)-2-phenoxy ethylamine-(1.0 mmol) triethylamine-and catalyst amount of DMAP was dissolved in 20 mL dichloromethane, then (R)-2-{4-[(3-chloro-5-trifluoromethylpyridin-2-yl)oxy]phenoxy}propanoic acyl chloride was added dropwise and stirred for 1 h at room temperature. When the reaction was complete, the mixture was washed with water and brine, dried over anhydrous sodium sulfate, and vacuumed to distillate solvent. Moreover, the crude product was purified with column chromatography silica gel using PE and EtOAc as eluent to give white solid 3a-m.p. 138~140C, yield 80.1% [alpha]20 D +20.33 (c 1, CH2Cl2); 1 H NMR (400 MHz, CDCl3) delta-7.85 (d, J = 2.2 Hz, 1H, pyridine), 7.50 (dd, J1 = 9.0, J2 = 2.2 Hz, 1H, pyridine), 7.29 (s, 1H, C6H5), 7.25 (s, 1H, C6H5), 7.04 (d, J = 9.0 Hz, 2H, C6H4), 6.94 (t, J = 9.0 Hz, 3H, C6H5), 6.84 (d, J = 8.7 Hz, 2H, C6H4), 4.67 (q, J = 6.8 Hz, 1H, CHCH3), 3.97~4.10 (m, 2H, COOCH2), 3.70 (m, 2H, OCH2), 1.58 (d, J = 6.8 Hz, 3H, CH3). EI-MS m/z 480.1 [M + ]. Analysis calculated for C21H21ClFN3O3S C 64.78, H 4.78, N 9.06; found C 64.76, H 4.70, N 9.03.

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

Reference:
Article; Hui, Yang Zi; Indian Journal of Heterocyclic Chemistry; vol. 28; 3; (2018); p. 385 – 387;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, 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 1758-46-9, HPLC of Formula: C8H11NO

Example 55; 6- (2-Phenoxy-ethylamino)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine Hydrochloride; Use a method similar to the General Procedure 5-1, using 3- (2, 2,2-trifluoroacetyl)- 6-trifluoromethanesulfonyloxy-2, 3,4, 5-tetrahydro-lH-benzo [dlazepine (100 mg, 0.23 mmol) and phenoxyethylamine (63 mg, 0.4 mmol) to give, after chromatography on silica gel eluting with hexane/EtOAc (85: 15) followed by SCX chromatography, 6- (2-phenoxy- ethylamino)-3- (2, 2,2-trifluoroacetyl)-2, 3,4, 5-tetrahydro-1H-benzo[d]azepine as a yellow oil. MS (ES+) m/z : 379 (M+H) +. Use a method similar to the General Procedure 1-1 to deprotect 6- (2-phenoxy- ethylamino)-3- (2, 2,2-trifluoroacetyl)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine (75 mg, 0.19 mmol). Purify by SCX chromatography to give the free base of the title compound. Use a method similar to the General Procedure 2-2 to give the title compound as a white solid. MS (ES+) m/z : 283 (M+H) +.; General Procedure 5-1; Dissolve the appropriately substituted 3- (2, 2, 2-trifluoroacetyl)-6-trifluoromethane- sulfonyloxy-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine (1 equiv. ), palladium (II) acetate (0.1- 0.4 equiv. ), BINAP (0.2-0. 8 equiv. ; BINAP/catalyst ratio 2: 1) and cesium carbonate (1.4- 3. 0 equiv. ) in toluene (0.2-0. 05 M solution). Add the amine (1-3 equiv. ), degas the mixture with vacuum/nitrogen or argon purge and heat at 80-110°C for 4-16 h. Cool the mixture to ambient temperature, dilute with EtOAc, filter through a pad of silica gel or through Celitet) washing with EtOAc or ether, and evaporate the solvent to obtain the crude mixture. Alternatively, partition the reaction mixture between brine or saturated aqueous NaHCO3 and EtOAc, ether or DCM, dry the organic layer over Na2S04, and concentrate to obtain the crude mixture. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc mixtures and further SCX chromatography if needed.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/82859; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 589-10-6, 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 589-10-6 as follows.

A solution of 0.24 g (10 mmol) of sodium hydride and15 ml of N, N-dimethylformamide was added50ml round bottom flask,Stirred at room temperature for 10 minutes, then 2.5 g (10 mmol) of compound 2 and 10 mmol were added2-phenoxyethyl bromide,And followed by thin layer chromatography to the end of the reaction, and then the reaction solution into 500ml ice water,Extracted three times with 100 ml of ethyl acetate, the organic phases were combined, the solvent was evaporated,The resulting residue was purified by silica gel column chromatography (V dichloromethane: V methanol = 100: 1) to give Compound 3 (2.3 g, yield 63%).

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangxi Normal University; Chen Zhenfeng; Liang Hong; Liu Yancheng; Lu Xing; Huang Kunyuan; (13 pag.)CN106478676; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Quality Control of ((2-Bromoethoxy)methyl)benzene

To a vigorously stirred solution of 15,2 g (100 mmol) 2-hydroxy-5-methoxy-benzaldehyde and 42.4 g (130 mmol) caesium carbonate in 350 ml DMF at 0°C was added 26.9 g (125 mmol) (2-Bromo-ethoxymethyl)-benzene (Adrich) in 50 ml DMF dropwisely. The reaction mixture was stirred vigorously at 70°C for 6h. The solvent was evaporated. 200 ml water and 200 ml ethyl acetate were added. The organic phase was separated. The aqueous phase was extracted three times with 100 ml ethyl acetate each. The combined organic phases were washed with 50 ml water and 50 ml brine. The organic phase was dried with magnesium sulphate and evaporated. The crude product was purified by silica column chromatography (gradient ethylacetate : hexane 1:3 –> 1:2). The desired product 2a was obtained in 86percent yield (24.6 g, 86 mmol) as yellow oil. MS-ESI: 287 (M+ + I , 100). Elementary analysis: C 71.31 percent H 6.34percent Determined: C 71.29percent H 6.35percent

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; Bayer Schering Pharma Aktiengesellschaft; EP1894915; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 148583-65-7, A common heterocyclic compound, 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, molecular formula is C9H12FNO, 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 18(6-Bromo-5-methyl-thieno[2,3-c lpyrimidin-4-yl)-(4-fluoro-2-isopropoxy-phA mixture of 6-bromo-4-chloro-5-methyl-thieno[2,3-c/]pyrimidine (456 mg), 4-fluoro-2- isopropoxy-phenylamine (293 mg) and p-toluenesulfonic acid (33 mg) in dioxane (6 ml) was stirred at 80C for three days. The reaction mixture was quenched withEtOAc and 10% aq. K2CO3 and filtered. The residue was washed with further EtOAc and dried to yield the title compound.Yield: 288 mgESI mass spectrum: m/z = 397 (M+H)+ 1 H NMR (400MHZ; d6DMSO; 20C): delta 8.47 (s, 2H), 8.34 (s, 1 H), 7.1 7-7.03 (m, 1 H),6.90-6.78 (m, 1 H), 4.88-4.76 (m, 1 H), 2.74 (s, 3H), 1 .35 (d, 6H).

The synthetic route of 148583-65-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; HIMMELSBACH, Frank; LEHMANN-LINTZ, Thorsten; REDEMANN, Norbert; SAUER, Achim; THOMAS, Leo; BLACK, Phillip; BLACKABY, Wesley; DANILEWICZ, John; LINNEY, Ian; AUSTEN, Matthias; SCHNEIDER, Martin; SCHREITER, Kay; WO2011/104338; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 450-91-9, These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-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.

To a solution of EDCI?HCl (573.2 mg, 2.99 mmol) in DMF (7 mL) and CH2Cl2 (7 mL) were successively added OxymaPure® (425.0 mg, 2.99 mmol) and S1 (1.00 g, 2.72 mmol) at room temperature. After stirring the reaction mixture for 5 min, 4-fluoro-2-methoxyaniline (470.6 mg, 2.99 mmol) dissolved in DMF (1 mL) and DIPEA (590 muL, 4.08 mmol) were added, the reaction mixture was stirred at the same temperature for 11 h. The volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and 1 N HCl aq. was added. The resulting mixture was extracted with ethyl acetate twice, the combined organic layers were washed with aqueous saturated NaHCO3 twice, H2O, brine and dried over Na2SO4. After filtration, the residue was concentrated under reduced pressure and dried in vacuo to give crude amide as brown solid. To the amide in DMF (9 mL) was added piperidine (240 muL, 4.08 mmol) and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate and H2O was added. The resulting mixture was extracted with ethyl acetate twice, the combined organic layers were washed with H2O, brine, dried over Na2SO4. Filtrate was concentrated and the resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane = 12/88 to 100/0) to give S2 (464.9 mg, 1.73 mmol, 64percent over 2 steps) as a pale brown oil.Pale brown oil; [alpha]D27 ?6.1 (c 0.44, CH3OH); 1H NMR (400 MHz, CD3OD) delta 8.01 (dd, J = 8.8 , 6.2 Hz, 1H), 6.84 (dd, J = 10.5, 2.7 Hz, 1H), 6.66 (ddd, J = 8.8, 8.6, 2.7 Hz, 1H), 3.89 (s, 3H), 3.46 (dd, J = 7.3, 5.6 Hz, 1H), 1.86?1.77 (m, 1H), 1.66?1.53 (m, 2H), 1.35?1.29 (m, 2H), 0.93 (d, J = 6.6 Hz, 3H), 0.92 (d, J = 6.6 Hz, 3H); 13C NMR (100 MHz, CD3OD) delta 176.3, 161.4 (d, J = 240.6 Hz), 152.7 (d, J = 10.2 Hz), 124.3 (d, J = 3.6 Hz), 123.4 (d, J = 9.5 Hz), 107.1 (d, J = 21.9 Hz), 100.2 (d, J = 27.0 Hz), 56.9, 56.6, 35.8, 34.2, 29.2, 23.0, 22.9; 19F NMR (376 MHz, CD3OD) delta ?117.4; IR (neat) nu 3019, 2959, 1673, 1611, 1531, 1465, 1415, 1216, 757, 669 cm?1; HRMS (ESI) calcd. for C14H22N2O2F m/z 269.1660 [M+H]+, found 269.1651.

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nonoyama, Akihito; Kumagai, Naoya; Shibasaki, Masakatsu; Tetrahedron; vol. 73; 11; (2017); p. 1517 – 1521;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 22236-10-8,Some common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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.

6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.09 g, 4.21 mmol) prepared as described above (Intermediate 2, 1.0 g, 3.86mmol) was dissolved in anhydrous acetonitrile (3 mL) and 4-difluoromethoxyaniline was added (1.34 g, 8.42 mmol). The mixture was heated at 180 C. for 600 s in a microwave (Emrys Optimizer model, Personal Chemistry). The solvents were removed under vacuum to give the desired product as a beige powder (1.3 g, 94.2%). The crude product was used for the subsequent step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Difluoromethoxy)aniline, its application will become more common.

Reference:
Patent; Kelly, Michael G.; Kincaid, John; Kaub, Carl J.; US2006/258689; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 645-36-3, name is 2,2-Diethoxyethanamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

1.5 g of 2-piperidone was dissolved in 75 mL of mesitylene, 248 muL of titanium tetrachloride was added thereto, and heated at 140C. A solution obtained by dissolving 4.02 g of aminoacetoaldehyde diethyl acetal to 45 mL of mesitylene was prepared, and was added dropwise to the previous mesitylene solution over 3 hours. The mixture was stirred at 140C for 70 hours, then cooled back to room temperature, and was extracted with a 2N aqueous solution of hydrochloric acid. The obtained aqueous layer was basified with a 5N aqueous solution of sodium hydroxide, and then was extracted with chloroform. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the purification was carried out by distillation under reduced pressure (3mmHg, 120C), to obtain 375 mg of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [44-1] as a pale yellow oily product.

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; BANYU PHARMACEUTICAL CO., LTD.; EP1790650; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 767-91-9, 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. 767-91-9, name is 2′-Methoxyphenyl acetylene, This compound has unique chemical properties. The synthetic route is as follows.

Cuprous iodide (9.5 mg, 0.05 mmol) was weighed out,Sodium carbonate (530 mg, 5 mmol),Tetrabutylammonium nitrite (288 mg, 1 mmol) and 2-methoxyphenylacetylene (132 mg, 1 mmol) were sequentially added into a 25 mL reaction vessel and the mixture was purged with nitrogen three times. Purified THF (4.0 mL), charged with CO2 (0.1MPa). Closed reactor, placed in a 25 C oil bath reaction 16h, after the reaction, open the valve on the reactor slowly release the remaining gas, and then the reaction vessel was transferred to a single port flask to concentrate, and with 5mL of deionized water Diluted and then extracted with n-hexane. The aqueous layer was acidified to pH = 1 at low temperature by addition of 1 M hydrochloric acid and extracted with ether. The organic phase was collected, washed with brine, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo. 2-Methoxyphenylacetophenic acid was obtained in a yield of 83%.

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

Reference:
Patent; Dalian University of Technology; Feng Xiujuan; Jia Lihong; Bao Ming; (19 pag.)CN107353194; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem