Ethers-buliding-blocks

Electric Literature of 202865-80-3, 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 202865-80-3 as follows.

To a mixture of 2-amino-5-[3-(t-butyl)dimethyl-silanoxypropyloxy]-1-(4-methylbenzyl)benzene (54 mg, 0.14 mmol), 4-bromo-2-fluoro-1-isopropoxybenzene (32.6 mg, 0.14 mmol), dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl (3.3 mg, 0.007 mmol), potassium t-butoxide (28.3 mg, 0.29 mmol) and toluene (2 mL) was added palladium acetate(II) (1.6 mg, 0.007 mmol) under nitrogen atmosphere, and the resulting mixture was stirred at 100C for 1 hour. The reaction mixture was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1-(4-chlorobenzyl)-3-[3-(t-butyl)dimethyl-silanoxypropyloxy]-6-(3-fluoro-4-isopropoxy phenylamino)benzene (69 mg, Yield: 92%) as brown oil. 1H-NMR (delta ppm TMS/DMSO-d6): 0.00(6H, s), 0.84 (9H, s), 1.21 (6H, d, J = 6.0 Hz), 1.84 (2H, q, J = 6.0 Hz), 2.22 (3H, s), 3.70 (2H, t, J = 6.0 Hz), 3.80 (2H, s), 3.92 (2H, t, J = 6.0 Hz), 4.27 (1H, q, J = 6.0 Hz), 6.32-6.42 (2H, m), 6.62 (1H, d, J = 3.0 Hz), 6.75 (1H, dd, J = 2.4 Hz, 8.4 Hz), 6.84-6.94 (1H, m), 6.97-7.08 (5H, m), 7.25 (1H, s).

According to the analysis of related databases, 202865-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., SDS of cas: 54314-84-0

To a solution of methyl isobutyrate 23 (5g, 49 mmol) in THF was added slowly a solution of LDA (52 mmol, generated from n-BuLi and diisopropyl amine) in THF at -78 0C, the reaction was stirred for 20 minutes. The resulting solution was treated with a solution of Benzyl 3-bromopropyl ether 22 in HMPA and stirred at -78 0C for 12 h, aq. HCI (1 N) was added and the resulting mixture extracted with ether, Organic layer washed with water, saturated NaHCO3, dried and concentrated, it was purified by to give the desired ester 24 (11.6 g, 80percent). 1HNMR (CDCI3) delta 7.36-7.26 (m, 5H), 4.49 (s, 2H), 3.65 (s, 3H), 3.45 (t, J = 6.5 Hz, 2H), 1.62-1.52 (m, 4H), 1.18 (s, 6H); 13C NMR (CDCI3) delta 178.3, 138.5, 128.3, 127.6, 127.5, 72.8, 70.5, 51.7, 42.0, 37.1 , 25.3, 25.1.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/158381; (2009); A1;,
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Application of 2734-70-5, 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. 2734-70-5, name is 2,6-Dimethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,6-dimethoxyaniline (0.51 g, 3.3 mmol) and 5-methylnicotinonitrile (0.39 g, 3.3 mmol) in toluene (10 ml) at 0° C. was added dropwise TMS-OTf (1.2 ml, 6.5 mmol). The resulting mixture was stirred at 0° C. for 10 min and heated to 110° C. for 2 days. The reaction mixture was cooled to 0° C., quenched with 1N HCl (10 mL) solution and diluted with EtOAc. The organic layer was washed with 1N HCl solution and dried over sodium sulfate, decanted and concentrated to give a brown oil. The residue was added to a silica gel (40 g) column and was eluted with 0-100percent 1percent Et3N/EtOAc in DCM. Collected fractions to give Compound 7a (0.65 g, 73percent yield) as an off white solid. MS m/z=272.2 (M+H). 1H NMR (500 MHz, CHLOROFORM-d) delta 8.90 (s, 1H), 8.56 (s, 1H), 8.24 (s, 1H), 7.07 (t, J=8.3 Hz, 1H), 6.68 (d, J=8.3 Hz, 2H), 4.76 (br s, 2H), 3.84 (s, 6H), 2.43 (s, 3H).

The synthetic route of 2,6-Dimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Pi, Zulan; Bilder, Donna M.; Brigance, Robert Paul; Finlay, Heather; Jiang, Wen; Johnson, James A.; Lawrence, R. Michael; Meng, Wei; Myers, Michael C.; Phillips, Monique; Tora, George O.; Zhang, Xiaojun; (59 pag.)US2017/275272; (2017); A1;,
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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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 768-70-7

A mixture of methyl 4-hydroxy-3-iodobenzoate (0.14 g, 0.50 mmol), 3-ethynylanisole (0.19 mL, 1.50 mmol), bis(triphenylphosphine)palladium(II) chloride (0.035 g, 0.050 mmol), copper(I) iodide (9.5 mg, 0.050 mmol) and 1,1,3,3-tetramethylguanidine (0.63 mL, 5.00 mmol) in N,lambda/-dimethylformamide (5 mL) under an atmosphere of argon was heated at 70 0C for 3 days. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using heptane:ethyl acetate (9:1) as the eluent, gave 0.13 g (91% yield) of the title compound.1H NMR (CDCl3) delta ppm 8.35 (dd, 1 H) 8.04 (dd, 1 H) 7.57 (d, 1 H) 7.49 (ddd, 1 H) 7.37 – 7.45 (m, 2 H) 7.10 (d, 1 H) 6.96 (ddd, 1 H) 3.98 (s, 3 H) 3.93 (s, 3 H); MS (EI) m/z 282 [M]+.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2009/64251; (2009); A1;,
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Related Products of 452-08-4, The chemical industry reduces the impact on the environment during synthesis 452-08-4, name is 2-Bromo-4-fluoro-1-methoxybenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 107 9-Fluoro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 207, structure 41 of Scheme XI, where R1 =H, R2 =F) 5-Fluoro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =F) In a 200-mL flask, a solution of 2-bromo-4-fluoroanisole (Aldrich: 4.00 mL, 30.8 mmol) in THF (50 mL) was cooled to -78 C. (CO2 /IPA). To this solution n-BuLi (Aldrich: 2.5M in hexanes; 12.4 mL, 31 mmol, 1.0 equivuiv) was added dropwise over a 30 min period. The reaction mixture was stirred at -78 C. for 60 min and treated with trimethylborate (Aldrich: 10.5 mL, 92.4 mmol, 3.0 equivuiv). The reaction mixture was allowed to slowly warm to rt, stirred overnight (12 h), and cooled to 0 C. (ice/H2 O). The solution was treated with 5% HCl until the pH reached 6. The reaction mixture was poured into sat’d NH4 Cl (80 mL) and extracted with CH2 Cl2 (3*100 mL). The extracts were washed with sat’d NH4 Cl (1*80 mL), combined, dried (MgSO4), filtered through a pad of Celite, and concentrated to afford 4.90 g (94%) of a white semi-solid. Data for 5-fluoro-2-methoxyphenylboronic acid: 1 H NMR (400 MHz, acetone-d6): 7.47 (dd, J=8.8, 3.3, 1H); 7.17 (m, 1H); 7.05 (dd, J=9.0, 3.9, 1H); 3.93 (s, 3H).

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-Bromo-4-fluoro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H13NO

Step C: To a solution of the acid (1.85 g, 7.6 mmol) from step B above and N-methyl morpholine (1.5 mL, 13.7 mmol) in dichloromethane (50 mL) at -20 C. was added isobutyl chloroformate (1.2 mL, 9.1 mmol) dropwise. The reaction solution was stirred at -20 C. for 45 minutes and then a solution of 3-(methoxybenzyl) methylamine (1.3 g, 8.4 mmol) in dichloromethane (10 mL) was added to it dropwise. The resultant solution was warmed to room temperature and stirred overnight. The reaction solution was then washed with water, saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (95:5 to 50:50 hexanes/ethyl acetate) to give the desired product (2.0 g, 78%) as a yellow oil: 1H NMR (CDCl3, 500 MHz) delta 7.96-7.86 (m, 3H), 7.59-7.37 (m, 2H), 7.34-7.26 (m, 2H), 7.04-6.78 (m, 4H), 4.70 (d, J=13.5 Hz, 2H), 3.80 (s, 3H), 3.10 (d, J=17.9 Hz, 3H).

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; AMR Technology, Inc.; US2007/21408; (2007); A1;,
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Application of 60792-79-2, The chemical industry reduces the impact on the environment during synthesis 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, I believe this compound will play a more active role in future production and life.

Example 6; Preparation of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(2-((E)-6-(4-hydroxy-6-methoxy-7- methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4- enamido)ethoxy)ethyl)docosa-4,7,10,13,16,19-hexaenamide (I-2); 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, and 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%).tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (1.47 mmol) was then taken up in CH3CN (10 mL) along with mycophenolic acid (470 mg, 1.47 mmol) and EDCI (310 mg, 1.62 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It is then diluted with EtOAc (50 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 620 mg of (E)-tert-butyl 2-(2-(6- (4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4- enamido)ethoxy)ethylcarbamate (83% yield).(E)-tert-Butyl 2-(2-(6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3- dihydroisobenzofuran-5-yl)-4-methylhex-4-enamido)ethoxy)ethylcarbamate (620 mg, 1.22 mmol) was taken up in 10 mL of 4 M HC1 in dioxane and allowed to stir at room temperature for 2 h. The resulting reaction mixture was concentrated under reduced pressure to afford the HCl salt of (E)-N-(2-(2-aminoethoxy)ethyl)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3- dihydroisobenzofuran-5-yl)-4-methylhex-4-enamide This material was taken up in CH3CN (10 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (400 mg, 1.22 mmol), HATU (510 mg, 1.34 mmol) and DIEA (640 muL, 3.66 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. It was then diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (5% MeOH in CH2Cl2) afforded 600 mg of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2- (2-((E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4- methylhex-4-enamido)ethoxy)ethyl)docosa-4,7,10,13,16,19-hexaenamide (68% yield). MS (EI) calcd for C43H60N2O7: 716.44; found 717 (M+1).

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, 2,2′-Oxybis(ethylamine) dihydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; US2011/213028; (2011); A1;,
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Electric Literature of 6443-69-2, 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. 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 1 (3.6 g, 20 mmol) and NaBr (2.2 g, 20 mmol) were dissolved in HOAc (10 mL). The mixture was treated dropwise with 30% H2O2 (2.4 mL, 20 mmol) at room temperaturefor 1 h. Then, the mixture was quenched with water (8 mL) and extracted with diethyl ether (3 × 10 mL). The combined organic phases were washed with saturated NaHCO3 (3 × 5 mL) until pH 7, the combined the organic layers were dried over anhydrous Na2SO4, and evaporatedin vacuo to afford yellow oil 2 (5.2 g) in quantitative yield. 1H NMR (400 MHz, CDCl3): delta 6.61 (s, 1H, ArH), 3.89(s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.84 (s, 3H, OCH3),2.37 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3): delta 152.2, 150.8, 141.1,133.4, 110.8, 109.5, 61.1 (OCH3), 60.9 (OCH3), 56.1(OCH3), 23.2(CH3). Spectroscopic data are according to the literature (Wanget al. 2016).

The synthetic route of 1,2,3-Trimethoxy-5-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qiu, Yong-Fu; Lu, Bin; Yan, Yi-Yu; Luo, Wan-Yue; Wang, Jin; Hu, Xiao; Chemical Papers; vol. 73; 11; (2019); p. 2745 – 2748;,
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Synthetic Route of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

Under the protection of nitrogen, take 6mol / L hydrochloric acid 10.0ml, down to 0 ,9.0 ml of compound III ((dimethylamino) -acetaldehyde-diethyl acetal) was added dropwise, hydrolyzed at 40 ° C and cooled to 0 ° C for standby (A).To 100 ml of absolute ethanol, 10.00 g of the intermediate IV, 0.80 g of lithium chloride were added in this order, and the temperature was lowered to 04.0 g of sodium ethoxide was added, and the mixture was stirred for 30 minutes. The stock solution A was added dropwise, and the prepared liquid A was added dropwise.After the reaction was continued for 40 min, 250 ml of ethyl acetate was added, stirred for 1.0 hr, filtered, and 125 ml of water was added to the filtrate. In ThereThe organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure to give intermediate II. The yield in this step was about 84percent.

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

Reference:
Patent; Chongqing Weipeng Pharmaceutical Co., Ltd.; Lie, Zeyan; Zhou, Xingguo; Li, Chunlin; Han, Gongchao; (6 pag.)CN104529800; (2017); B;,
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Electric Literature of 82830-49-7, These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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 FIFTY-EIGHT: Synthesis of Ligand 24 (Figure 17); In a round-bottomed flask nBuLi (10 mmol, 4 rnL of a 2.5 M solution in hexanes) was added drop-wise to a solution of 1 ,4-dimethoxyfluorobenzene (10 mmol, 1.56 g) in THF (120 mL) at -78 0C. The mixture was stirred at -78 0C for a further 30 min, generating solution A. nBuLi (20 mmol, 8 mL of a 2.5 M solution in hexanes) was added drop-wise to a solution of 2,3-benzofuran (20 mmol, 2.36 g, 2.20 mL) in THF (30 mL) at 0 0C. After 2 h at this temperature the mixture was cooled to -78 0C and magnesium bromide (20 mmol, 3.68 g) added and this mixture stirred until the solid dissolved. This solution was then added via cannula to solution A and the mixture maintained at -78 0C for 1 h. The solution was then allowed to warm to room temperature overnight. The solution was then cooled to 0 0C and a solution of iodine (12 mmol, 3.5 g) in THF added via cannula. The mixture was allowed to warm to room temperature and sodium sulfite (saturated aq. solution) added. The mixture was extracted with EtOAc, the organic layer washed (water, then brine), dried and the solvent removed under reduced pressure. The residue was purified in 2 batches by column chromatography on a Biotage SP4 (hexane-EtOAc, 98:2 – 80:20) to give the iodide.

The synthetic route of 82830-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2009/76622; (2009); A2;,
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