Category: ethers-buliding-blocks

These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, 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: 588-63-6

Intermediate 110 1,1-Dimethylethyl (2/?,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-({[3-(phenyloxy)propyl]oxy} methyl)- 1 -pyrrolidinecarboxylate1 ,1-Dimethylethyl (2R,4S)-4-{[(1 ,1-dimethylethyl)(dimethyl)silyl]oxy}-2-(hydroxymethyl)-1- pyrrolidinecarboxylate (0.6 g, 1.810 mmol) was diluted in THF (1 ml) to give a colorless solution. The resulting mixture was cooled down to 0 0C under argon. Then sodium hydride (0.217 g, 9.05 mmol) in THF (2ml_) was added to give a white suspension followed by [(3-bromopropyl)oxy]benzene 3-bromopropyl phenyl ether (0.779 g, 3.62 mmol) in THF (1 ml). The resulting mixture was stirred at rt over the week end (96 h).The reaction was then quenched by addition of water at 0 0C. The THF was removed in vacuo and the resulting crude was diluted in DCM and washed with 0.1 M HCI, sat NaHCOs using a hydrophobic frit. The organic layer was then concentrated in vacuo to yield a colorless oil. This resulting oil was loaded onto a 5 g silica SPE cartridge, then eluted sequentially with hexane DCM and EA. The corresponding fractions were combined and evaporated to afford the title compound (0.45 g, 53percent). LC-MS: m/z, 466 (M+H), rt 1.67 min.

The synthetic route of (3-Bromopropoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/26197; (2009); A1;,
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Application of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-(5-amino-4-fluoro-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (1.36 g, 4.28 mmol, 1.00 eq), 4-methoxy-N-methylbenzylamine (0.971 g, 6.42 mmol, 1.50 eq) and DBU (0.960 mL, 6.42 mmol, 1.50 eq) were combined in NMP (20 mL) and heated at 180¡ã C. under Ar overnight. The mixture was cooled to RT and poured onto H2O (200 mL). The resulting solids were collected by filtration, rinsed very well with H2O, dried on the filter to dampness and then dissolved in EtOAc. The solution was dried (MgSO4), filtered and evaporated to afford 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (1.86 g, 100percent yield) as a brittle brown foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): delta 8.45 (s, 1H), 7.63 (s, 1H), 7.16 (d, J=8.8 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 6.86-6.82 (m, 1H), 6.57 (d, J=9.6 Hz, 1H), 6.29 (s, 1H), 4.88 (br s, 2H), 4.85 (s, 2H), 3.69 (s, 3H), 3.52 (s, 3H), 3.07 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 433.3 [M+H]+.

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

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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538-86-3, name is (Methoxymethyl)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. HPLC of Formula: C8H10O

General procedure: A mixture of nitriles (5 mmol), methyl ethers (6 mmol) and Fe(ClO4)3¡¤H2O (5percentmol) was placed in a round bottom flask. Then the reaction mixture was heated at 100 ¡ãC for the given time. After completion of the reaction monitored by thin layer chromatography (TLC), 10 ml water was added into reaction system and extracted with ethyl acetate (3 ¡Á 20 ml). The organic layers were collected, combined, washed with water (3 ¡Á 20 ml), dried over anhydrous Na2SO4, and concentrated under vacuum. The pure products (1a?1k and 2a?2p) were obtained by directly passing through a silica gel (200?300 mesh) column using petroleum ether/ethyl acetate (10:1?5:1).

The synthetic route of 538-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yin, Guibo; Yan, Bin; Chen, Junqing; Ji, Min; Journal of the Iranian Chemical Society; vol. 16; 6; (2019); p. 1355 – 1363;,
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Application of 74654-07-2, The chemical industry reduces the impact on the environment during synthesis 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, I believe this compound will play a more active role in future production and life.

Weigh A4 (0.841 g, 1 mmol) in 15 ml DMF in a 25 ml one-neck flask and add NMM (N-methylmorpholine) (112 muL, 1.0 mmol) and HATU Benzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate) (0.57 g, 1.5 mmol) was activated for 30 min.Add PEG163 (0.163g, 1mmol) with stirring for 1h, then warmed to room temperature for reaction for 10h. The reaction was stopped and dichloromethane was added for extraction. The mixture was washed twice with water and twice with saturated NaCl solution. The organic phase was distilled under reduced pressure to give 0.91g of light yellow solid. Column chromatography white solid 0.651g, 65.08% yield.

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-(2-Methoxyethoxy)ethoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Jiao Tong University; Shen Yumei; Gong Bing; Tan Lianjiang; Shao Zhifeng; Yang Qinglai; Li Xiaowei; Jiang Yu; Zhang Zhen; (42 pag.)CN104693258; (2017); B;,
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Application of 261762-35-0, 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. 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a flask containing a mixture of 5-bromo- 1 ,2-difluoro-3-methoxy-benzene (1.1 g, 4.93 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (0.85 g, 5.92 mmol) in 1,4-dioxane (10 mL) was added t-BuONa (0.95 g, 9.86 mmol), Pd2(dba)3 (92 mg, 0.10 mmol) and Ru-Phos (92 mg, 0.20 mmol) under N2. After being heated with stirring at 100 C overnight, the reaction mixture was cooled to rt and diluted with water (20 mL), The resulting mixture was extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrousNaSO and concentrated in vacuo to give 8-(3,4-difluoro-5-methoxy-phenyl)-1,4-dioxa-8- azaspiro[4.5]decane (1.57 g), which was used in the next step without further purification.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, 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. COA of Formula: C8H8Br2O2

1, 4-diamino -2, 5- […] (1, 4-diamino-2, 5-dimethoxybenzene) (16.9mmol) and 30 parts by weight of diethyl ether (70 ml) at -78 C 1.55N of agitating n-BuLi (16.8mmol) in 11 ml of hexane of. input additional are mixed together. 1.5 in the maintaining -78 C mixture adaptation stirring time. Dichloro d methyl thread column (8.4mmol) and 30 parts by weight of diethyl ether in the -78 C a 2 ml is closed after charging additional adaptation stirring during night at room temperature. After 1.5 reflux time was are input, in water and and stirring. possibility layer hexane and water extraction of water and balancer in a washing machine after the washing phosphorous in the magnesium sulfate expresses water after to remove, is every. D-1 compounds via fractional distillation (45% yield) is obtained.

The synthetic route of 2674-34-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG DISPLAY CO., LTD.; SIN, IN AEY; LEE, SUNG JAE; BIN, JONG KWAN; LEE, BANG SOOK; SAW, BO MIN; YU, YOUNG JU; (45 pag.)KR2015/64794; (2015); A;,
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Synthetic Route of 1159512-64-7, 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 1159512-64-7 as follows.

(a) 4-bromo-2-fluoro-3-(trifluoromethoxy)aniline To a solution of 2-fluoro-3-(trifluoromethoxy)aniline (1.0 g, 5.13 mmol) dissolved in DMF (2 mL) at 0 C. was slowly added a solution of cold N-bromosuccinimide (0.91 g, 5.13 mmol) dissolved in DMF (6 mL) over 5 min. The reaction mixture was stirred at 0 C. for 1 h, extracted with EtOAc (125 mL) and washed with water (3*25 mL). The combined aqueous layers were extracted with EtOAc (75 mL). The combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated to produce the title compound as a dark colored liquid (1.27 g, 90% yield). (m/z): [M+H]+ calcd for C7H4BrF4NO 273.94. found 273.8.

According to the analysis of related databases, 1159512-64-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H13NO

A solution of (3-methoxy-benzyl)-methyl-amine (0.590 g, 3.93 mmol) and TEA (1.1 ml_) in DCM (5 mL) was treated with 2-bromo-1-thiophen-3-yl-ethanone (1.11 g, 5.11 mmol). After 16 h at 23 0C, the mixture was poured onto water and extracted with DCM. The organic layer was collected, dried (Na2SO4), and concentrated to give the desired product (1.149 g, >100% crude). 1H NMR (CDCI3): 8.24 (ddLambda J = 2.9,’ 1.2, 1 H), 7.57 (dd, J = 5.1 , 1.2, 1 H), 7.28 (dd, J = 5.1 , 2.9, 1 H), 7.26-7.21 (m, 1 H), 6.94-6.90 (m, 2H), 6.83-6.79 (m, 1 H), 3.79 (s, 3H), 3.65 (s, 2H), 3.64 (s, 2H), 2.37 (s, 3H).

According to the analysis of related databases, 41789-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/66197; (2006); A1;,
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Reference of 886762-08-9, 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 886762-08-9 as follows.

General procedure: To a stirred solution of 5-bromo-2-(trifluoromethoxy)aniline (540 mg, 2.11 mmol) in pyridine was added pyridine-2-sulfonylchloride (410 mg, 2.31 mmol and the mixture was heated to 45C for 4 h. After quenchingwith water the mixture was extracted with CH2C12, dried over MgSO4 and evaporated togive a solid (769 mg) that was used without further purification. To a mixture of the aforementioned crude solid and (chloromethoxy)ethane (329 mg, 3.49 mmol) in DMF at room temperature was added a 60% w/w dispersion of Nail in mineral oil (140 mg, 3.49 mol) and the mixture was stirred for 1 h. After quenching with water the mixture was extracted with CH2CI2, dried with MgSO4 and evaporated to give a solid which waspurified by column chromatography eluting with hexanes/EtOAc 3:1. The title compound was isolated as a colourless oil (857 mg, 89%, 2 steps).?H NMR [400 MHz, CDCI3I 6 8.75 (ddd, J =4.8, 1.6, 1.0 Hz, 1H), 7.90-7.82 (m, 2 H), 7.54-7.46 (m, 3 H), 7.10 (dddd, J = 8.9, 1.9,1.8, 1.8 Hz, 1 H), 5.21 (br s, 2 H), 3.79 (q, J = 7.0 Hz, 2 Fl), 1.20 (t, J = 7.0 Hz, 3 H). LRMS (APCI?) calcd for C13H10BrF3N2O3S 409 (M-EtO), found 409.

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); 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. 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H9F2NO2

To a stirred solution of 2,6-difluoro-3,5-dimethoxyaniline (0.4g, 2.11 mmol) and 6-chloro nicotinaldehyde (0.44g, 3.17 mmol) in toluene (20mL) was added catalytic PTSA and molecular sieves (0.4 g). Heated the reaction mass to reflux in a Dean Stark apparatus for overnight. Concentrated the reaction mass and diluted the residue with methanol, cooled to 0 C and added sodium borohydride (0.3g, 8.4 mmol). Stirred the reaction mass at room temperature for lh and further heated to 70 C for lh. Quenched the reaction mass with ice cold water, warmed to room temperature and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (3x30mL). The organic phase was washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The crude material was purified by silica column chromatography to afford desired title compound (0.2g, 30%) as a solid. LCMS: m/z = 315.1 (M+H)+.

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 651734-54-2.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
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