Category: ethers-buliding-blocks

Synthetic Route of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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 5-carbamoyl-2-fluoro-4-hydroxybenzene-1 -sulfonyl chloride (lnt-2, 1 .4 g) in DCM (15 mL) at 0 C was added pyridine (0.670 mL) followed by 4-isopropyxyaniline (0.696 mL). The reaction mixture was allowed to warm to RT and was stirred for 16 hr. The reaction mixture was poured into water (10 mL) and extracted with DCM (2 x 15 mL). The combined DCM extracts were washed with saturated brine (10 mL), dried over sodium sulfate and concentrated under reduced pressure to afford the crude product (900 mg). The crude product was purified by silica gel column chromatography, eluting with 30-40% EtOAc/petroleum ether to afford the titled compound (700 mg). LCMS m/z 369.09 (M+H)+. NMR (400 MHz, DMSO-c/6) delta ppm 1 .19 (d, J=5.92 Hz, 6 H) 4.36 – 4.56 (m, 1 H) 6.58 – 6.84 (m, 2 H) 6.84 – 7.10 (m, 3 H) 8.06 (br. s., 1 H) 8.31 (d, J=8.1 1 Hz, 1 H) 8.62 (br. s., 1 H) 10.06 (s, 1 H) 14.06 (br. s., 1 H).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
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Synthetic Route of 16452-01-0, 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. 16452-01-0, name is 3-Methoxy-4-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 47 Part E. 4-Isothiocyanato-2-methoxy-1-methyl-benzene To a solution of 3-methoxy-4-methylaniline (50 mg, 0.36 mmol) in DCM (2 mL) was added thiocarbonyldiimizaole (68 mg, 0.38 mmol) and the mixture was stirred at rt for 3 h. The mixture was concentrated under reduced pressure, and the residue was dissolved in MeOH (3 mL) and filtered through an SCX cartridge (CUBX1HL, 500 mg cartridge, United Chemical Technologies, Bristol Pa., USA). The filtrate was concentrated under reduced pressure to afford the title compound which was used as such for the subsequent step without further purification.

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-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US6596747; (2003); B2;,
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These common heterocyclic compound, 64465-53-8, name is 4-Fluoro-3-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. Computed Properties of C7H8FNO

Aqueous hydrobromic acid (48%, 2.41 mL) was added to 4-fluoro-3-methoxyaniline (1.0 g, 7.1 mmol) in water (10 mL) and the resulting mixture was cooled to 0 C in an ice bath. A solution of sodium nitrite (538 mg, 7.8 mmol) in water (5 mL) was added dropwise during 15 min while maintaining the temperature between 0-5 0C. The resulting diazoniumsalt solution was added to a suspension of copper(I) bromide (1.12 g, 7.8 mmol) in water (5 mL) which had been pre-heated to 75 C. The mixture was shaken thoroughly, aqueous hydrobromic acid (48%, 12.07 mL) was added and the solution was stirred at ambient temperature for 16 h. Excess water was added and the product was extracted with diethyl ether and the combined organic extracts were washed with aqueous saturated sodium chloride, dried over magnesium sulfate, filtered and the solvent was evaporated in vacuo to give 1.02 g (70% yield) of the title compound.: 1H-NMR (DMSO-J6): delta 7.36 (dd, J= 7.78, 2.26 Hz, 1 H), 7.23-7.17 (m, 1 H), 7.14-7.09 (m, 1 H), 3.86 (s, 3 H); MS (EI) (m/z, %) 204,206 (100), 189,191 (23), 161,163 (45)

The synthetic route of 4-Fluoro-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/58602; (2007); A2;,
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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. 4179-19-5, name is 3,5-Dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,5-Dimethoxytoluene

Step 1: 4-(2,4-Dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid[0423] To a suspension of l,3-dimethoxy-5-methyl-benzene (5.1O g, 33.55 mmol) and succinic anhydride (3.69 g, 36.91 mmol) in nitrobenzene (100 mL) was added AlCl3 (8.9 g, 67.10 mmol). The reaction mixture was stirred at room temperature for 16 hours then carefully poured into aqueous NaOH. The pH was adjusted to 10 with solid NaOH and the aqueous solution washed with dichloromethane. The pH of the aqueous solution was adjusted to 3 with concentrated HCl and extracted with EtOAc. The organic extracts were dried and concentrated in vacuo. The residue was triturated dichloromethane to give 4-(2,4-dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid as a pale yellow solid (3.7 g, 43%). 1H NMR (400 MHz, MeOD-d4) delta 6.44 (s, IH), 6.40 (s, IH), 3.80 (s, 3H), 3.78 (s, 3H), 3.03 (t, J = 8.1 Hz, 2H), 2.60 (t, J = 8.1 Hz, 2H), 2.19 (s, 3H).

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 4179-19-5.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
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38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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. SDS of cas: 38336-04-8

(1) Take 5g of p-fluoronitrobenzene dissolved in 50ml of acetonitrile,5.72 g under ice bath2-benzyloxyethylamine (A) is added to the above solution,Then add 9.5 ml of triethylamine,Reaction at 50C for 8 hours,A yellow clear solution is obtained,The reaction solution was concentrated under reduced pressure,Dissolved in 200 ml of dichloromethaneWash 50 ml of water three timesThe organic phases are combined and dried over anhydrous sodium sulfate.After filtration, spin down to give a crude product.The crude product was purified by column chromatography to give intermediate II 4.5 g as a yellow oil.Yield 48.1%.

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tierxi (Nanjing) Pharmaceutical Research And Development Co., Ltd.; Li Yantao; Mao Yu; Zhang Chi; Liu Chun; Cui Xilin; (13 pag.)CN107586291; (2018); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., name: ((3-Bromopropoxy)methyl)benzene

Compound 3F: 1 -[3-(Benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H- pyrazoleA mixture of 4-(4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1 /-/-pyrazole (5.0 g, 26 mmol), potassium carbonate (4.27 g, 30.9 mmol) and 1-bromo-3-benzyloxypropane (6.20 g, 27.0 mmol) in DMF (20 mL) was stirred at 80 °C overnight, quenched with water (20 mL) and extracted with EtOAc (100 mL). The organic layer was washed with water (2 x 30 mL), brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ISCO system: EtOAc/Heptane = 30- 70percent) to afford 7.67 g of the title compound as a light-yellow oil (87percent). 1H NMR (CDCI3, 400 MHz): delta = 7.80 (s, 1 H), 7.66 (s, 1 H), 7.30-7.36 (m, 5H), 4.48 (s, 2H), 4.28 (t, J = 6.8 Hz, 2H), 3.43 (t, J = 5.8 Hz, 2H), 2.17 (m, 2H), 1.33 (s, 12H). MS (ES+): m/z = 343.36 [MH+]. HPLC: iR = 4.20 min ( ZQ3: polar_5 min).

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; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); A1;,
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Related Products of 588-63-6, These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

General procedure: Maslinic acid (MA, 1equiv) was dissolved in dry DMF (5mL), and finely grounded potassium carbonate (5 equiv) was added. After 60min of stirring at room temperature, the corresponding alkyl or benzyl bromide (2equiv) was added, and stirring was continued for 18h. The mixture was poured into an ice cold aq. HCl (5percent, 50mL), and the white precipitate was filtered off. Chromatographic purification (silica gel, hexane/ethyl acetate, 7:3) and recrystallization (ethanol) afforded the product.

Statistics shows that (3-Bromopropoxy)benzene is playing an increasingly important role. we look forward to future research findings about 588-63-6.

Reference:
Article; Siewert, Bianka; Pianowski, Elke; Obernauer, Anja; Csuk, Rene?; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 594 – 615;,
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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 19056-40-7 as follows. HPLC of Formula: C7H8BrNO

3-Methoxy-4-bromoaniline (10.0 g, 0.0494 mol) and dimethylacetylene dicarboxylate(7.46 g, 0.0525 mol) were combined in methanol (71 mL) and Dowtherm (140 mL) and refluxed under nitrogen for 18 hrs. The reaction was cooled and concentrated to give an oily residue and additional Dowtherm (20 mL) was added. This solution was added dropwise via syringe to Dowtherm (120 mL) at 250 0C and allowed to stir at 250 0C for an additional 15 min (precipitate observed). The reaction mixture was cooled to room temperature, solids filtered and washed with hexanes to give 14.4 g solid. EPO The solid was resuspended in dichloromethane (200 mL) and stirred for 30 min. The solid was filtered to give to give 34 (13.8 g, 90percent yield). LRMS (M+H)+ = 312.

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/119061; (2006); A2;,
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Related Products of 168971-68-4, These common heterocyclic compound, 168971-68-4, name is 1-Bromo-2-fluoro-4-(trifluoromethoxy)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.

A mixture of 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene Int-172-38 (12.8 g, 49.4 mmol), benzophenone imine (10 mL, 59.3 mmol), Pd2(dba)3 (1.1 g, 1.23 mmol), XantPhos (2.8 g, 4.9 mmol) and NaOtBu (5.7 g, 59.3 mmol) in 1,4-dioxane (100 mL) was stirred and heated at 100 C overnight. After cooling to room temperature, the mixture was concentrated. The residue was then partitioned between EtOAc and H2O, and the organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using hexanes/EtOAc (0 to 5% EtOAc in hexanes). The product was dissolved in THF (100 mL), and 1M aqueous HCl (50 mL) was added. After being stirred at room temperature for 1h, the mixture was partitioned between EtOAc and H2O. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using hexanes/EtOAc (0 to 20% EtOAc in hexanes). The product 30 was obtained as pale brown oil in 30% yield (5.4 mg). LCMS: (M+1) m/z = 196.

Statistics shows that 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 168971-68-4.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BLACKTHORN THERAPEUTICS, INC.; ROBERTS, Edward; GUERRERO, Miguel A.; URBANO, Mariangela; ROSEN, Hugh; JONES, Rob; LAXAMANA, Candace Mae; ZHAO, Xianrui; TURTLE, Eric Douglas; (331 pag.)WO2018/170492; (2018); A1;,
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Synthetic Route of 1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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.

Add NaH (0.47 g, 11.8 mmol) to a solution of morpholin-3-one (Vieles, P.; Seguin, J., Bulletin de Ia Societe Chimique de France, 1953, 287-9) (1.0 g, 9.9 mmol) in DMF (10 ml) at room temperature. Stir for 30 min, add (2-bromo-ethoxymethyl)-benzene (2.2 g, 10.2 mmol), and stir at room temperature for 18 h. Dilute with water and extract with EtOAc (2x). Combine the organics, dry, and concentrate. Purify by flash chromatography using 0 – 5% MeOH in CH2Cl2, to give the product as an oil. (1.7 g, 74%). 1H NMR (400 MHz, CDCl3): delta 7.28 (m, 5H), 4.48 (s, 2H), 4.13 (s, 2H), 3.80 (t, 2H, /=5.1 Hz), 3.65 (m, 2H), 3.59 (dd, 2H, 7=7.5, 2.6 Hz), 3.48 (t, 2H, J=5.1 Hz).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/66174; (2006); A1;,
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