Tag: M.W=100-200

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., Recommanded Product: 3-Fluoro-4-methoxyaniline

Step 2. To a solution of l-(6-chloropyrazin-2-yl)-2-methyl-lH-benzo[d]imidazole (96 mg, 0.36 mmol) and 3-fluoro-4-methoxyaniline (71 mg, 0.5 mmol) in THF (1 mL) at room temperature was added KOt-Bu (1M in THF, 1 mL, 1 mmol). The mixture was reacted for 5 minutes, then the reaction was quenched with AcOH and the product partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was dried, concentrated and purified by chromatography on silica gel (gradient from ethyl acetate:hexane 1:2 to ethyl acetate: methanol 5: 1). The fractions were concentrated and the residue was washed with an ethyl acetate: ether mixture, then filtered and dried to provide the title compound as a yellow/brown solid (39 mg, 25 percent). ]H NMR (DMSO-i delta 9.93 (s, 1H), 8.31 (s, 1H), 8.25 (s, 1H), 7.61 – 7.68 (m, 2H), 7.51 – 7.55 (m, 1H), 7.32 – 7.36 (m, 1H), 7.26 – 7.26 (m, 1H), 7.23 – 7.30 (m, 2H), 7.14 (t, J = 9.1 Hz, 1H), 3.79 (s, 3H), 2.63 (s, 3H); MS m/z 350 (ESI) [M+H]+.

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; BAIAZITOV, Ramil; CHOI, Soongyu; DU, Wu; HWANG, Seongwoo; LEE, Chang-Sun; LIU, Ronggang; MOON, Young-Choon; PAGET, Steven, D.; REN, Hongyu; SYDORENKO, Nadiya; WILDE, Richard, Gerald; WO2015/76800; (2015); A1;,
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Reference of 1535-73-5, A common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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 mixture of compound 3B-1 (2.00 g, 8.98 mmol, 1.0 eq) and compound 3D-1 (1.91 g, 10.8 mmol, 1.2 eq) in isopropanol (20 mL) was added TFA (1.02 g, 8.98 mmol, 1.0 eq) in one portion at 20 ¡ãC under nitrogen. The mixture was stirred at 90 ¡ãC for 18 hours. LC-MS (ET15060-21-P1A1) showed the reaction was completed. The resulting suspension was cooled, and the product was filtered off, washing with a small volume of dichloromethane (10 mL) to give compound 3D-2 (3.00 g, 8.26 mmol, 91.9 percent yield) as yellow solid which was used for next step directly. ln NMR: ET15060-21-P1A1 400 MHz DMSO-d6 9.68 (s, 1H), 8.71 (d, J = 8.8 Hz, 1H), 8.15 (d, J = 6.0 Hz, 1H), 8.03 (s, 1H), 7.91 (dd, J = 8.4, 1.2 Hz, 1H), 7.71 (d, J = 8.4, Hz, 1H), 7.45 (t, J = 8.4 Hz, 1H), 6.98 (d, J = 8.0 Hz, 1H), 6.90 (d, J = 6.0 Hz, 1H), 2.48 (s, 3H).

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUTRIS PHARMA LTD.; SHELACH, Noa; (76 pag.)WO2019/26065; (2019); A2;,
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These common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, 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. HPLC of Formula: C8H8F3NO

2-Methoxy-5 (trifluoromethyl) aniline (commercially available) (109.7 mg, 0.551 mmol) was dissolved in 14 mL dichloromethane. Saturated aqueous [NAHCO3] solution (14 mL) was added and the mixture was cooled to [0 C.] While stirring, the mixture was treated with phosgene by addition to the organic layer via syringe in one portion (0.95 mL, 1.92 mmol). The mixture was then stirred vigorously for 0.5 h, then the layers were separated. The aqueous layer was extracted once with dichloromethane and the combined organics were dried [(MGS04),] filtered and the dichloromethane was removed in vacuo. The isocyanate residue was added to the aminonaphthyl pyrimidine ether (186 mg, 0.551 mmol) in 2 mL anhydrous THF. The reaction mixture was left stirring at room temperature overnight and then concentrated in vacuo and triturated with ether to provide 250 mg of a pink solid. The product was purified by column chromatography on silica gel, eluting with 1: 9: 90 [NH40H] : MeOH: [CH2CL2] to provide 110 mg of the title compound as a tan foam.

The synthetic route of 2-Methoxy-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/14870; (2004); A1;,
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These common heterocyclic compound, 321-28-8, name is 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. Recommanded Product: 1-Fluoro-2-methoxybenzene

Step 1. Preparation of 1-(3-fluoro-4-methoxyphenyl)-2-phenyl-ethan-1-one. Aluminum chloride (42.17 g, 316 mmol) and dichloromethane (350 mL) were cooled to 2 C. and phenylacetylchloride (40.50 g, 262 mmol) in dichloromethane (30 mL) was added. 2-Fluoroanisole (32.77 g, 260 mmol) in dichloromethane (30 mL) was added. The cooling bath was removed, and the mixture was stirred for 1 hour. The reaction mixture was poured into concentrated HCl (150 mL), filtered through diatomaceous earth, washed with saturated aqueous NaHCO3, dried over MgSO4, and concentrated. A white solid was obtained by crystallization from dichloromethane/hexane (29.2 g, 46%): mp 105-106 C.

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

Reference:
Patent; G. D. Searle & Co.; US5859257; (1999); A;,
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Reference of 111-95-5,Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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 the product from step 46 2 (1.00 g, 5.29 mmol) in 94 ACN (20 mL) was added 43 bis(2-methoxyethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and the reaction mixture was heated to 70 C. for 16 hours thereafter. The reaction was cooled and concentrated. The residue was partitioned with EtOAc and water. The organic layer was separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (SiO2, 10/1 hexanes-EtOAc to 1/1) afforded 950 mg (63% yield) of the desired adduct as a yellow solid: 1NMR (300 MHz, CDCl3) delta 7.47 (bs, 2H), 3.77 (t, J=5.7 Hz, 4H), 3.52 (t, J=5.4 Hz, 4H), 3.25 (s, 6H). 13C NMR (75 MHz, CDCl3) ? 154.7 (s), 152.0 (s), 120.9 (s), 119.5 (s), 95.8 (s), 71.0 (t), 59.1 (q), 50.0 (t). LCMS (50-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=4.91 min on 250 mm column, (M+H)+=286, (M+Na)+=308, (M+Na+ACN)+=349.

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MediBeacon Inc.; Debreczeny, Martin P.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (54 pag.)US2019/125901; (2019); A1;,
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Related Products of 6851-80-5, 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. 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL ¡Á 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

The chemical industry reduces the impact on the environment during synthesis 1-(2-Methoxyphenyl)-N-methylmethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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Synthetic Route of 82830-49-7,Some common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, molecular formula is C8H9FO2, 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 10 mL oven-dried Schlenk tube was charged with magnesium (57.6 mg, 2.4 mmol) and anhydrous THF (1.5 mL), 5 drops of diisobutylaluminium hydride (DIBAL) was added and stirred for 5 min to activate magnesium. 3-bromo-2,4,6-triisopropyl-4?-(trifluoromethyl)-1,1?-biphenyl (852 mg, 2 mmol) was added potion-by-potion with vigorous stirring. The tube was capped with a rubber septum and was heated to 70 C. for 2 h (A). In another 10 mL oven-dried Schlenk tube was charged with 2-fluoro-1,4-dimethoxybenzene (156 mg, 1 mmol) and anhydrous THF (3.5 mL). The tube was cooled to -78 C. and 1.6 M n-BuLi solution in hexane (0.64 mL, 1 mmol) was added dropwise over 10 min under vigorous stirring. The mixture was stirred at -78 C. for 40 min (B). A was transferred into to B by syringe over 15 min at -78 C. An additional 1 mL of THF was used to rinse the reaction and was also transferred to B. The combined reaction mixture was stirred at -78 C. for another 1 h and then slowly warmed to room temperature and vigorously stirred for overnight. At this time, the mixture was cooled to 0 C. using ice bath, and iodine (762 mg, 3 mmol) in 4 mL anhydrous THF was added drop-wise over 5 min, then the reaction mixture was stirred for 30 min, and then warmed to stir at room temperature for 2 h. Then, the mixture was quenched with saturated Na2S2O3 (aq.) solution until the red color of bromine disappeared. The aqueous phase was extracted with Et2O (10 mL¡Á3) and the combined organic phases were dried over anhydrous MgSO4. After concentration, the crude product was purified by silica gel chromatography (EtOAc/petroleum ether=1/20) followed by crystallization in methanol to get a white solid (226 mg, 37%), labeled as 25MeOTIP-I. 1H NMR (600 MHz, Chloroform-d) delta 7.66-7.61 (m, 3H), 7.46-7.39 (m, 2H), 7.23 (s, 1H), 6.90 (d, J=8.9 Hz, 1H), 6.82 (d, J=8.9 Hz, 1H), 3.91 (s, 3H), 3.71 (s, 3H), 2.65 (p, J=7.2 Hz, 1H), 2.37 (dp, J=25.3, 6.9 Hz, 2H), 1.23 (d, J=6.8 Hz, 3H), 1.11 (dd, J=10.3, 6.9 Hz, 6H), 1.04 (d, J=6.9 Hz, 3H), 0.80 (d, J=7.2 Hz, 3H), 0.71 (d, J=7.2 Hz, 3H) ppm. 13C NMR (151 MHz, Chloroform-d) delta 152.40 (d, J=40.7 Hz), 147.01, 146.10, 145.85, 141.68, 137.11 (d, J=48.9 Hz), 136.32, 132.12, 131.30, 128.68 (d, J=32.3 Hz), 124.02, 119.94, 110.00, 109.30, 56.81, 55.31, 32.51, 30.93, 29.72, 24.61 (d, J=4.2 Hz), 24.00, 23.69, 22.94 (d, J=12.1 Hz) ppm. 19F NMR (376 MHz, CDCl3) delta=-62.15 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-1,4-dimethoxybenzene, its application will become more common.

Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (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. 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, A new synthetic method of this compound is introduced below., name: 1-Isopropoxy-2-vinylbenzene

A vacuum dried Schlenk flask was charged with imidazolium hydrochloride salt 4b (129 mg, 0.26 mmol, 1.15 eq.) and 10 mL dry toluene was introduced into the flask using a syringe. The white suspension thus formed was vigorously agitated and to it was introduced under an argon atmosphere solid KHMDS (95 %, 60 mg, 0.28 mmol, 1.23 eq.). The suspension turned homogeneous and was left to stir for 30 min. To this was then introduced, under an argon atmosphere, Grubbs first generation catalyst (190 mg, 0.23 mmol, 1.0 eq.) and the mixture was left stirring for another 2 hours at room temperature. The toluene was then evaporated in vacuuo to give a dark brown coloured semisolid. No purification of this mixture was attempted, however as significant degradation and loss of intermediate complex was observed. The crude brown semisolid was then redissolved in 10 mL of DCM and to this was introduced CuCl (91 mg, 0.92 mmol, 4 eq.) and 1-isopropoxy-2-vinylbenzene (75 mg, 0.46 mmol, 2 eq.) and the mixture stirred at 40C for 3 hours. The reaction was then cooled and DCM evaporated in vacuuo to give a dark green coloured semisolid. The semisolid was first washed with dry, distilled pentane (2¡Á50 mL) and dried under high vacuum. The resulting green powder was loaded onto a column of silica gel soaked in pentane. This was then eluted successively using pure pentane to remove unreacted vinylbenzene and then a 1/1 mixture of pentane/DCM and finally pure DCM to remove a green band which was collected and dried under high vacuum to yield a green coloured amorphous powder. C41H58N2OCl2Ru (766.88) calc. for C 64.21, H 7.62, N 3.65, found C 64.36, H 7.68, N 3.49.

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:
Article; Shahane, Saurabh; Toupet, Loic; Fischmeister, Cedric; Bruneau, Christian; European Journal of Inorganic Chemistry; 1; (2013); p. 54 – 60;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3-Fluoro-4-methoxyaniline

To a sample of 113 (1.011 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solutionof 3-fluoro-p-anisidine (0.541 g, 3.8 mmol) in acetone (10 mL) followed by additionof NaOH (1.52 mL, 2.5 N, 3.8 mmol) and water (3 mL). The reaction mixture was allowed to stir at reflux for about 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane ; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (silica gel, 70: 30 hexanes : ethyl acetate) yielded light yellow solid compound 114 (0.581 g, 42percent), mp98 C ; TLC (silica gel, 30: 70 ethyl acetate: hexanes), Rf 0.36 ; MS (ESI):m/z 369 (39.1), 368 (22.1), 367 (M+H, 100), 273 (3.2), 271 (10.7). Compound 115 was obtained as a by-product (0.159 g) via column chromatography (silica gel, 70: 30 hexanes : ethyl acetate), mp181 C ; TLC (silica gel, 30: 70 ethyl acetate: hexanes), Rf 0.17 ; MS (ESI): nez 472 (M+H, 100), 261 (1.5).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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Reference of 6851-80-5,Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: To a mixture of the corresponding secondary amines 7a-d (0.77mmol), anhydrous K2CO3 (106.2mg, 0.77mmol) and KI (8.6mg, 0.052mmol) in CH3CN (10mL) were added the appropriate intermediates 12-14 (0.60mmol). The reaction mixture was warmed to 60-65C and stirred for 12-15h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Water (30mL) was added to the residue and the mixture was extracted with dichloromethane (30mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixture of CH2Cl2/CH3OH as eluent, obtaining the corresponding 7-O-MOM-4?-O-modified genistein derivatives.

The synthetic route of 6851-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qiang, Xiaoming; Sang, Zhipei; Yuan, Wen; Li, Yan; Liu, Qiang; Bai, Ping; Shi, Yikun; Ang, Wei; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 314 – 331;,
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