Category: ethers-buliding-blocks

Electric Literature of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-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 4-bromo-2-methoxyaniline (4.0 g, 20 mmol) in concentrated hydrochloric acid (40 mL) was added dropwise sodium nitrite (1.4 g, 21 mmol) and water (2 mL) solution while maintaining at -20C, and the mixture was stirred at the same temperature for 15 min. The mixture was warmed to 0C, and the mixture was stirred at the same temperature for 20 min, and further, a solution of tin chloride·2 hydrate (17 g, 74 mmol) in concentrated hydrochloric acid (140 mL) was added dropwise to the reaction mixture while maintaining at -20C. After stirring at the same temperature for 10 min, and the mixture was stirred at room temperature for 40 min. The precipitate was collected by filtration, and washed with ice water and diethyl ether. To the filtered material was added ethyl acetate and 10% aqueous potassium carbonate, and the insoluble material was filtered off. The aqueous layer of the filtrate was extracted with ethyl acetate, the organic layer was combined, and the mixture was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give the title compound as a pale yellow solid (3.4 g, 78%). 1H NMR (CDCl3) delta: 3.49 (2 H, br), 3. 84 (3 H, s), 5.61 (1 H, br), 6.85 – 6.88(2 H, m), 7.06 (1 H, dd, J=2.1, 8.7 Hz).

Statistics shows that 4-Bromo-2-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 59557-91-4.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2455380; (2012); A1;,
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These common heterocyclic compound, 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, 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. Product Details of 103291-07-2

PREPARATION 12 3-(4-Fluoro-3-methoxyphenyl)pyridine A solution of 15.6 g (76.1 mmole) of 1-bromo-4-fluoro-3-methoxybenzene in 67 ml of tetrahydrofuran was added dropwise, with stirring, under nitrogen, to 1.92 g (79.1 mmole) of dried magnesium turnings. Stirring was continued for 1 hour and then the supernatant liquid was removed to give a solution of 4-fluoro-3-methoxyphenylmagnesium bromide. In a separate flask, 7.3 ml (76.1 mmole) of 3-bromopyridine was dissolved in 23 ml of tetrahydrofuran and 880 mg (0.76 mmole) of tetrakis-triphenylphosphine palladium was added. This latter mixture was heated to reflux, and the above Grignard solution was added dropwise, during 10 minutes, with stirring. The resulting mixture was refluxed for 1 hour and then it was stirred overnight at room temperature. The reaction mixture was diluted with 100 ml of water, followed by 100 ml of 10% hydrochloric acid, and the resulting solution was washed with dichloromethane. The aqueous phase was basified with sodium bicarbonate and then it was extracted with dichloromethane. The combined extracts were dried using potassium carbonate and evaporated in vacuo to give 12.3 g (79%) of the title compound as a reddish oil.

The synthetic route of 4-Bromo-1-fluoro-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4593037; (1986); A;,
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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. 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. Product Details of 16452-01-0

Intermediate 18To a suspension of 4-methyl-3-(methyloxy)aniline (Intermediate 17, 1.86 g) in water (100 mL)/H2S04 (30 mL, 563 mmol) at 0C a solution of sodium nitrite (1.029 g, 14.91 mmol) in water (10 mL) was slowly added and the reaction mixture was stirred for 30 minutes at 0 C. The reaction mixture was slowly added to a solution of H2S04 98% (20 mL) in Water (80 mL) pre-heated at 90C and stirred at this temperature for 1 h. After cooling the mixture was extracted with Et20 (2x200mL), the organic layer was dried on sodium sulphate, filtered and evaporated to afford the title compound (1.86 g) as a red/brown oil.H-NMR (400 MHz, DMSO-c/6) delta ppm: 9.14 (1 H, br.s), 6.87 (1 H, d), 6.35 (1 H, d), 6.24 (1 H, dd), 3.71 (3H, s), 2.01 (3H, s); UPLC_B: 0.63 min, 137 [M-H]-.

The synthetic route of 16452-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; DECOR, Anne; FONTANA, Stefano; HAMPRECHT, Dieter; LARGE, Charles; MARASCO, Agostino; WO2011/69951; (2011); A1;,
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Reference of 107622-80-0, 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 107622-80-0 as follows.

Example 104 2-(4-methyl-2,5-dioxo-4-imidazolidinyl)-N-(4-phenoxybenzyl)acetamide Hydantoin 103a (50 mg, 0.30 mmol) was coupled to 4-phenoxybenzylamine using general coupling method A to give 45 mg of the product hydantoin. MS found:(M+H)+=354.

According to the analysis of related databases, 107622-80-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sheppeck, James E.; Duan, Jingwu; Xue, Chu-Biao; Wasserman, Zelda; US2003/130273; (2003); A1;,
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These common heterocyclic compound, 143-24-8, name is 2,5,8,11,14-Pentaoxapentadecane, 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. Quality Control of 2,5,8,11,14-Pentaoxapentadecane

Comparative Example 1 was conducted in the same manner as in Example 1 except that 4 mmole of 3-hydroxypyridine was used as promoter instead of imidazole and except the reaction conditions. 1 mmole of Co2(CO)8 was used and 200 mmole of ethylene oxide was used. The reaction conditions of Comparative Example 1 were shown in Table 2.

The synthetic route of 2,5,8,11,14-Pentaoxapentadecane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co. Ltd.; US6348632; (2002); B1;,
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Electric Literature of 38336-04-8, 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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 6-(1-((tert-butoxycarbonyl)amino)-2-ethoxy-2-oxoethyl)-5-fluoronicotinic acid 0.95 g (2.78 mmol) in dichloromethane (13 mL) was added triethylamine 1.15 mL (8.33 mmol, 3 eq), N-(3- dimethylaminopropyl)-N¢-ethylcarbodiimide hydrochloride 0.59 g (3.05 mmol, 1.1 eq), 1- hydroxybenzotriazole hydrate 0.41 g (3.06 mmol, 1.1 eq), followed by 2-(benzyloxy)ethan-1-amine ) 0.5 mL (3.33 mmol, 1.2 eq) and the reaction was stirred at RT for 18 h. The mixture was diluted with dichloromethane, washed with water/brine, dried over sodium sulfate and concentrated. The product was purified by flash chromatography on silica gel (30% ethyl acetate/hexanes) to afford the title compound. ESI-MS m/z 476 (MH)+.

The synthetic route of 2-(Benzyloxy)-1-ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VENATORX PHARMACEUTICALS, INC.; BURNS, Christopher J.; DAIGLE, Denis; CHU, Guo-Hua; HAMRICK, Jodie; BOYD, Steven A.; ZULLI, Allison L.; MESAROS, Eugen F.; CONDON, Stephen M.; TROUT, Robert E. Lee; MYERS, Cullen L.; XU, Zhenrong; (327 pag.)WO2019/226931; (2019); A1;,
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Synthetic Route of 458-52-6, These common heterocyclic compound, 458-52-6, name is 2-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.

Step A 2-Fluoro-4-methoxyphenyl isocyanate To a solution of 13.75 g (0.0967 mole) of 2-fluoro-4-methoxyaniline in 120 mL of toluene was slowly added over a period of 30 minutes a solution of 19.13 g (0.0967 mole) of trichloromethyl chloroformate in 30 mL of toluene. During the addition the temperature rose to 35° C. The reaction mixture was stirred without external heating for 30 minutes and then heated at reflux for approximately 17 hours. At the end of this time all of the solvent was removed by distillation, leaving 2-fluoro-4-methoxyphenyl isocyanate as a purple liquid, which was used immediately in Step B.

The synthetic route of 458-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5344812; (1994); A;; ; Patent; Theodoridis; George; US5798316; (1998); 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. 13468-02-5, name is N,N-Dimethyl-2-phenoxyethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 13468-02-5

The N, N – dimethyl – N – [(2 – phenoxy) ethyl] amine (1.65 g, 10 . 00 mmol) dissolved in dichloromethane (10 ml) in, under ice bath slowly […] sulfonic acid (2.5 ml The system for the ice in the pouring, adding dichloromethane (50 ml), separating the organic layer, drying with anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude intermediate 6 a, directly Used for the next step reaction.

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; Chengdu Xiandao Pharmaceutical Development Co., Ltd.; Li Jin; Wang Wei; Chu Hongzhu; Lv Kaizhi; Liu Lichuan; Nong Yunhong; Chen Wei; (17 pag.)CN110256416; (2019); A;,
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Application of 349-65-5, A common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

According to Method C4, 2-methoxy-5-(trifluoromethyl)aniline was reacted with phosgene followed by 3-(-2-(N-methylcarbamoyl)-4-pyridyloxy)aniline to afford the urea. Entry 12: 4-Chloropyridine-2-carbonyl chloride HCl salt was reacted with ammonia according to Method A2, Step 3b to form 4-chloro-2-pyridinecarboxamide.

The synthetic route of 349-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2002/165394; (2002); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); A1;,
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Related Products of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 × 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (3 mL) in a compound 7e (29.5 mg, 100 mumol),1-ethynyl -3,5-dimethoxy-benzene (40.6 mg, 250 mumol), CuSO4 (3.2 mg, 20 mumol) and Na. ascorbate (20.0 mg, 100mumol) theOf the desired compound was prepared using. After stirring at room temperature the reaction mixture for 66 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 30: 1 CH2Cl2 / MeOH) Compound 2e by using as a brown solid form (23.1mg, 51%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxyphenylacetylene, its application will become more common.

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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