Category: ethers-buliding-blocks

Electric Literature 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.

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

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:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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Application of 41789-95-1, A common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 D: To a cold (0 C. ) and stirred solution of 3-methoxy-N-benzylamine (46 g, 305 mmol) and diisoproplyethylamine (40 mL, 276 mmol) in CH2Cl2 (500 mL) was added the product obtained from Step C (71 g, 276 mmol) in CH2Cl2 (500 mL) solution. The reaction was then stirred at 0 C. for 2 hours. It was washed with water (500 mL), saturated aqueous NaHCO3 (500 mL), brine, dried and concentrated to give the desired product as a light yellow liquid (107 g, crude, quant.): 1H NMR (300 Hz, CDCl3) delta 8.43 (s, 1H), 7.94-7.92 (m, 2H), 7.51 (d, J=5.4 Hz, 1H), 7.40 (d, J=5.4 Hz, 1H), 7.25-7.21 (m, 1H), 6.93-6.80 (m, 3H), 3.83 (s, 2H), 3.76 (s, 3H), 3.67 (s, 2H), 2.40 (s, 3H); ESI-MS m/z 326 [M+H]+.

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Molino, Bruce F.; Liu, Shuang; Guzzo, Peter R.; Beck, James P.; US2006/52378; (2006); A1;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 solution of sodium nitrite (1 .78 g, 25.87 mmol) in water (5 mL) was slowly added to a cooled (-10 C) suspension of 5-bromo-2-methoxyaniline (5.0 g, 24.87 mmol) in 6N HCI aq. (13 mL) so as to keep the internal temperature below 0 C. The mixture was stirred for another 20 mm at 0 C, then a solution of stannous chloride dihydrate (14.1 g, 72.1 mmol) in conc. aq. HCI (25 mL) was added slowly. The reaction mixture was stirred an additional 1 .5 h at 0 C. The pH of the reaction mixture was carefully adjusted to -8 with sat. aq. NaHCO3. The mixture was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by trituration with pentane to give the title compound. MS (ESl+) m/z 217.0 (M(79Br)+H).

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher; EHARA, Takeru; (134 pag.)WO2017/103888; (2017); 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. 767-91-9, name is 2′-Methoxyphenyl acetylene, A new synthetic method of this compound is introduced below., Recommanded Product: 2′-Methoxyphenyl acetylene

1-Ethynyl-2-methoxybenzene (2a, 265 mg, 2 mmol) and benzyl azide (266 mg, 2 mmol) were added to a 1 : 1 water-tert-butyl alcohol mixture (8 mL). A freshly prepared 1 M aqueous solution of sodium ascorbate (200 muL, 0.2 mmol) and an aqueous solution of CuSO 4 ¡¤ 5 H 2 O (65 muL, 5 mg, 0.02 mmol) were then added in succession, and the mixture was stirred for ~14 h at room temperature (TLC). The mixture was diluted with 30 mL of ice water and kept for 15 min in an ice bath, and the white precipitate was filtered off, thoroughly rinsed with cold water (2 ¡Á 15 mL), and dried under reduced pressure. Yield 474 mg (89%), off-white solid. 1 H NMR spectrum, delta, ppm: 8.11 s (1H), 7.58 d (2H, J = 7.4 Hz), 7.42 t (1H, J = 8.5 Hz), 7.34-7.28 m (3H), 7.16 d (1H, J = 7.1 Hz), 7.00-6.94 m (2H), 6.13 s (2H), 3.70 s (3H). 13 C NMR spectrum, delta C , ppm: 159.5, 139.5, 136.7, 131.6, 129.2, 128.5, 128.1, 126.5, 120.3, 109.2, 104.1, 56.1, 54.0. Mass spectrum: m/z 266.1214 [M + H] + . Calculated for C 16 H 16 N 3 O: 266.1217.

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jabeen; Khera; Iqbal; Asgher; Russian Journal of Organic Chemistry; vol. 55; 9; (2019); p. 1416 – 1422; Zh. Org. Khim.;,
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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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,3-Dibromo-5-methoxybenzene

step 2-To a solution of 57b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (97:3 to 95:5) to afford 58.

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; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
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Reference of 70627-52-0,Some common heterocyclic compound, 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, molecular formula is C20H16FNO, 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 2): To a solution of TiCl4 (18.2 ml, 0.165 mol) in CH2Cl2 (600 ml) at 0 C., was added titanium isopropoxide (16.5 ml, 0.055 mol). After 15 min, the product of Step 1 (49.0 g, 0.17 mol) was added as a solution in CH2Cl2 (100 ml). After 5 min., diisopropylethylamine (DIPEA) (65.2 ml, 0.37 mol) was added and the reaction mixture was stirred at 0 C. for 1 h, the reaction mixture was cooled to -20 C., and 4-benzyloxybenzylidine(4-fluoro)aniline (114.3 g, 0.37 mol) was added as a solid. The reaction mixture was stirred vigorously for 4 h at -20 C., then acetic acid was added as a solution in CH2Cl2 dropwise over 15 min, the reaction mixture was allowed to warm to 0 C., and H2SO4 (2N) was added. The reaction mixture was stirred an additional 1 h, the layers were separated, washed with water, separated and the organic layer was dried. The crude product was crystallized from ethanol/water to obtain the pure intermediate.

The synthetic route of 70627-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2005/96307; (2005); A1;,
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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 50592-87-5 as follows. category: ethers-buliding-blocks

In an appropriate vessel for microwave was mixed 1-bromo-6-methoxyhexane (183 mg ; 0.94 mmol ; 1eq) and tributylphosphine (209 mg (95% pure : 220 mg) ; 1.03 mmol ; 1.1 eq) under inert atmosphere (glove box). Then the mixture was irradiated under microwave (200W) at 130C for 2 hours. The obtained viscous mixture was washed, triturated and centrifuged twice with Et2O, then the supernatant was removed and the obtained residue was taken up into DCM and dried over high vacuum. It led to a pale yellow oil (338 mg ; 0.85 mmol ; 90%). 1H-NMR (CDCl3, 400MHz): delta 3.36 (t, 2H, J 6.4 Hz), 3.31 (s, 3H), 2.41 (m, 8H), 1.47-1.61 (br, 18H), 1.41 (quint, 2H, J 7.2), 0.96 (t, 9H, J 6.6 Hz). 13C-NMR (101 MHz ; CDCl3): delta 72.5, 58.7, 30.7, 29.3, 25.7, 24.1, 22, 19.5, 19, 13.6 ; 9 signals obscured or overlapping. 31P-NMR (162 MHz ; CDCl3): delta 33.78. ESI MS : 317.3 m/z : M+ ; 713.5 m/z : [Br-M+]M+. Elemental analysis: calc % (C19H42BrOP 1/3 CH2Cl2): C, 53.24 ; H, 9.85. Found %: C, 52.94 ; H, 10.22.

According to the analysis of related databases, 50592-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brunel, Frederic; Lautard, Christelle; Garzino, Frederic; Giorgio, Suzanne; Raimundo, Jean M.; Bolla, Jean M.; Camplo, Michel; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3770 – 3773;,
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Application of 366-99-4, A common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

28.a. 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone (This product is obtained according to Sugasawa T; Toyoda T; Adachi M; Sasakura K, J. Am. Chem. Soc., 100 (1978), p.4842-4852). Boron trichloride (1M in heptane, 156 ml, 156 mmol) is added dropwise, under an argon atmosphere at 0¡ã C. to a solution of 3-fluoro-4-methoxy-aniline (20 g, 142 mmol) in anhydrous dichloromethane (200 ml). The pink suspension thus obtained is maintained under agitation for 5 minutes, then propionitrile (33 ml, 420 mmol) is added dropwise followed by aluminium trichloride (20.8 g, 156 mmol) in small portions. The reaction medium is heated under reflux for 3 hours, cooled down to 0¡ã C., hydrolyzed by cautiously adding 2N hydrochloric acid (100 ml), then heated at reflux for 45 minutes. After cooling down to 0¡ã C. a precipitate is obtained which is filtered out, washed with dichloromethane, then taken up in water (300 ml). The aqueous phase is basified to an alkaline pH, extracted with dichloromethane then ethyl acetate. The organic phase is dried (MgSO4) then evaporated to produce a crude product which is purified by column chromatography (SiO2, AcOEt/Hpt: 1/99 to 20/80). 15.3 g of a yellow solid is obtained. NMR-1H (CDCl3): 1.20 (t, 3H); 2.92 (q, 2H); 3.83 (s, 3H); 6.2 (s, 2H); 6.40 (d, 2H); 7.32 (d, 2H). IR (KBr): 857; 1148; 1240; 1561; 1583; 1662.

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

Reference:
Patent; Societe de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6815546; (2004); B2;,
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Synthetic Route of 20781-20-8, These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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 1: synthesis of methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate (86) A mixture of 2,4-dimethoxybenzylamine (58.7 mmol, 8.81 ml, 9.81 g), methyl 5-chloro-4-nitrothiophene-2-carboxylate (45.1 mmol, 10 g) and potassium carbonate (180 mmol, 24.94 g) were stirred at rt in Acetonitrile (226 mL) for 1 h. Reaction was quenched with water and the resulting precipitate was collected to give methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate 86 (15.5 g, 97%). NMR (400 MHz, CDCl3) 3.82 (s, 3H), 3.85 (s, 3H), 3.86 (s, 3H), 4.45 (d, J=5.9 Hz, 2H), 6.46 (dd, J=8.2 Hz and 2.3 Hz, 1H), 6.50 (d, J=2.3 Hz, 1H), 7.20 (d, J=8.2 Hz, 1H), 7.99 (s, 1H), 8.89 (br s, 1). (m/z)=353 (M+H)+.

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (2013); A1;,
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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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Bromo-4-methoxy-2-methylbenzene

This experiment was carried out four times. Tributyl(methoxy)stannane (400 g, 1.24 mol), 1-bromo-4-methoxy-2-methylbenzene (250 g, 1.24 mol), prop-1-en-2-ylacetate (187 g, 1.87 mol), palladium(ll) acetate (7.5 g, 33 mmol) and tri-otolylphosphine (10 g, 33 mmol) were stirred together in toluene (2 L) at 100 00 for 18 hours. After it had cooled to room temperature, the reaction mixture was treated with aqueous potassium fluoride solution (4 M, 400 mL) and stirred for 2 hours at 40 00. The resulting mixture was diluted with toluene (500 mL) and filtered through diatomaceousearth; the filter pad was thoroughly washed with ethyl acetate (2 x 1.5 L). The organic layer from the combined filtrates was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 5% ethyl acetate in petroleum ether) provided the product as a yellow oil. Combined yield:602 g, 3.38 mol, 68%. LCMS m/z 179.0 [M+H]. 1H NMR (400 MHz, CDCI3) oe 7.05 (d,J=8.3 Hz, 1H), 6.70-6.77 (m, 2H), 3.79 (5, 3H), 3.65 (5, 2H), 2.22 (5, 3H), 2.14 (5, 3H).

The synthetic route of 27060-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
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