Category: ethers-buliding-blocks

Synthetic Route of 887581-09-1,Some common heterocyclic compound, 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, molecular formula is C8H10BrNO, 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: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Bromo-5-methoxyphenyl)methanamine, its application will become more common.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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Synthetic Route of 20781-20-8, 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 20781-20-8 as follows.

A mixture of 3-hydroxyphthalic anhydride (1.24 g, 7.6 mmol), 2,4-dimethoxybenzylamine (1.14 mL, 7.6 mmol) and acetic acid (5 mL) was heated at 80C for 24 hours. The mixture was allowed to cool and diluted with water (20 mL). The white solid was collected by filtration, washed well with water and dried to give the title compound (1.73 g, 73%). 1H NMR (DMSOd6) 11.00 (1 H, s), 7.62 (1 H, dd), 7.29 (1 H, d), 7.21 (1 H, d), 6.90 (1 H, d), 6.56 (1 H, d), 6.43 (1 H, dd), 4.59 (2H, S)1 3.79 (3H, s), 3.72 (3H, s). MS: [M-H+] 314.

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
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These common heterocyclic compound, 80936-82-9, name is 4-(Methoxymethyl)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. Safety of 4-(Methoxymethyl)aniline

Step 2: Synthesis of 7-(tert-butyl)-N-(4-(methoxymethyl)phenyl)-4-(methylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide 7-(tert-butyl)-5-iodo-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine obtained in step 1, 103 mg of 4-(methoxymethyl)aniline, 90 mul of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 24 mg of 1,1′-bis(diphenylphosphino) ferrocene-palladium (II) dichloride-dichloromethane complex were added to 1 mL of DMA, and the mixture was stirred in a carbon monoxide atmosphere at 110 C. for 2 hours. The obtained reaction solution was purified by silica gel chromatography (developing solvent: hexane-ethyl acetate), concentrated, and purified again by basic silica gel chromatography, followed by concentration, thereby obtaining 52 mg of the title compound.

The synthetic route of 4-(Methoxymethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); A1;,
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Related Products of 944317-92-4, 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. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

The synthetic route of 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H12O2

General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.2 mmol) and PhI(OAc)2 (0.2 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure monobrominated compounds 2.

The synthetic route of 1515-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shibata, Ayako; Kitamoto, Sara; Fujimura, Kazuma; Hirose, Yuuka; Hamamoto, Hiromi; Nakamura, Akira; Miki, Yasuyoshi; Maegawa, Tomohiro; Synlett; vol. 29; 17; (2018); p. 2275 – 2278;,
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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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H10N2O

To a solution of 1.35 g of tert.-butoxycarbonyl-methylamino-propanoic acid in 5OmL DCM were added 3.4 mL of DIPEA, 81 mg of DMAP, 1.0 g of HOBt, 1.5 g of EDC and 0.91 g of 3-methoxybenzene-1 ,2-diamine. The resulting mixture was stirred at rt for 3 h and then quenched with water. The organic phase was washed with sat. aq. NaHCO3, dried over MgSO4 and concentrated on vacuo to yield 2.9 g of [2-(2-amino-3-methoxy- phenylcarbamoyl)-ethyl]-methyl-carbamic acid tert. -butyl ester as brown oil. LC-MS: tR = 0.72 min; [M+H]+: 324.35.

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 37466-89-0.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/132679; (2008); A1;,
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Reference of 1515-81-7,Some common heterocyclic compound, 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, molecular formula is C9H12O2, 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: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), thiol (1.0 mmol), p-methoxybenzylmethyl ether (167 mL,167 mg, 1.10 mmol), TMSOTf (271 muL, 333 mg, 1.50 mmol), anddiisopropylethylamine (244 muL, 181 mg, 1.40 mmol). The homogenous mixture was stirredovernight and then passed through a column of silica (2 cm x 1 cm) with Et2O.The solvent was removed in vacuo and the residue was purified by columnchromatography (0-2% EtOAc/hexanes).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methoxy-4-(methoxymethyl)benzene, its application will become more common.

Reference:
Article; Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; Confair, Danielle N.; Tetrahedron Letters; vol. 55; 37; (2014); p. 5213 – 5215;,
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18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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. Computed Properties of C8H8Br2O

l-Bromo-4-(2-bromoethoxy)benzene (95 mg, 0.34 mmol) was added to a mixture of N-[2-(3-azetidinyloxy)-5,6-dichloro-3-pyridinyl]-2-chloro-4-pyridinecarboxamide (i.e. the product of Step C) (100 mg, 0.28 mmol) and N,N-diisopropylethylamine (76 mL, 0.42 mmol) in acetonitrile (3 mL), and the reaction mixture was heated at 60 C overnight. The cooled solution was treated with saturated aqueous sodium bicarbonate solution (2 mL) and water (2 mL), and then diluted with dichloromethane before being filtered through a tube containing Celite diatomaceous filter aid, eluting with dichloromethane. The residue after concentration was purified by chromatography (silica gel, ethyl acetate to 5% methanol in ethyl acetate) to give the title product, a compound of the present invention, as a pale yellow oil (84 mg)..H NMR delta 8.88 (s, 1H), 8.62 (d, 1H), 8.28 (br s, 1H), 7.77 (d, 1H), 7.62 (d, 1H), 7.37 (d, 2H), 6.78 (d, 2H), 5.35 (m, 1H), 3.99 (t, 2H), 3.92 (t, 2H), 3.42 (br s, 2H), 2.95 (t, 2H).

The synthetic route of 18800-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; CLARK, David Alan; LAHM, George, P.; WO2012/12366; (2012); A1;,
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Synthetic Route of 634-36-6, A common heterocyclic compound, 634-36-6, name is 1,2,3-Trimethoxybenzene, molecular formula is C9H12O3, 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: A pyrex test tube containing solid of 1,3,5-trimethoxybenzene (1a, 0.3 mmol), carbon tetrabromide (0.075 mmol), AQN-2-CO2H (0.03 mmol) and dry EtOH (5 mL) was irradiated for 20 h at roomtemperature with stirring by a 21W fluorescent lamp under air. The reactionmixture was concentrated in vacuo, quenched with aq Na2S2O3 and extractedwith EtOAc. The organic layer was dried over MgSO4 and concentrated invacuo. Purification of the residue by flash chromatography on silica gel(hexane/ethyl acetate = 6:1) provided 2-bromo-1,3,5-trimethoxybenzene (2a)(66.8 mg, 90%,) as a white solid.

The synthetic route of 634-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanaka, Masanori; Kamito, Yuji; Lei, Cui; Tada, Norihiro; Itoh, Akichika; Tetrahedron Letters; vol. 56; 43; (2015); p. 5886 – 5888;,
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Reference of 707-07-3, 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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

4-(2-Azidoethyl)phenyl 4-0-benzoyl-2,6-di-0-benzyl-p-D-galactopyranoside (16)To a solution of 15 (1 .17 g, 2.31 mmol) in toluene (15 mL) were added trimethylortho- benzoate (0.64 mL, 3.72 mmol) and p-TsOH (1 18 mg, 0.62 mmol). The mixture was stirred at 45C overnight, then concentrated and the residue dissolved in 90% aq AcOH (15 mL). The solution was stirred for 2 h at 60C, concentrated, and the residue was purified by flash chromatography (petroleum ether/EtOAc, 9:1 to 7:3) to yield 16 (1 .30 g, 2.14 mmol, 93%) as a colorless oil. (0231) [a]D20 -8.4 (c 1.00, CHCI3); 1H NMR (500 MHz, CDCI3): delta 2.83 (t, J = 7.3 Hz, 2H, (0232) CH2CH2N3), 3.44 (t, J = 7.3 Hz, 2H, CH2CH2N3) 3.60-3.66 (m, 2H, H-6), 3.87 (dd, J = 7.4, (0233) 9.6 Hz, 1 H, H-2), 3.92 (dd, J = 3.5, 9.6 Hz, 1 H, H-3), 3.96 (t, J = 6.2 Hz, 1 H, H-5), 4.41 , 4.48 (A, B of AB, J = 1 1 .7 Hz, 2H, CH2Ph), 4.78 (A of AB, J = 1 1 .2 Hz, 1 H, CH2Ph), 4.99- (0234) 5.07 (m, 2H, H-1 , CH2Ph), 5.63 (d, J = 2.8 Hz, 1 H, H-4), 7.06, 7.12 (AA, BB’ of AA’BB’, J = 8.5 Hz, 4H, C6H4), 7.18-7.35 (m, 10H, 2 C6H5), 7.43 (t, J = 7.8 Hz, 2H, C6H5), 7.56 (t, J = 7.4 Hz, 1 H, C6H5), 8.04-8.09 (m, 2H, C6H5); 13C NMR (126 MHz, CDCI3): delta 34.62 (0235) (CH2CH2N3), 52.63 (CH2CH2N3), 68.61 (C-6), 70.25 (C-4), 72.21 (C-3), 73.28 (C-5), 73.71 , 75.13 (2 CH2Ph), 79.15 (C-2), 101 .89 (C-1 ), 1 17.07 (2C, C6H4), 127.76, 127.78, 128.04, 128.29, 128.39, 128.49, 128.58, 129.57 (12C, 3 C6H5), 129.93 (2C, C6H4), 130.10, 132.46, 133.38, 137.79 (6C, 3 C6H5), 138.06, 156.17 (C6H4), 166.38 (CO); ESI-MS: m/z: calcd for C35H35N3Na07 [M+Na]+: 532.24, found: 532.28; IR (film): 2102 cm”1 (N3).

The chemical industry reduces the impact on the environment during synthesis (Trimethoxymethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITAET BASEL; ERNST, Beat; HERRENDORFF, Ruben; STECK, Andreas; YANG, Fan; WO2015/136027; (2015); A1;,
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