Author: Jessica.F

Reference of 321-28-8, 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5-Bromo-2-chlorobenzoyl chloride 9b (124 g, 0.49 mol)Was dissolved in dichloromethane (600 mL)Cooled to -5 C,2-fluoroanisole (61.8 g, 0.49 mol) was added,Anhydrous aluminum chloride (133 g, 1.0 mol) was added in portions,The resulting mixture was stirred at room temperature for 4 hours.The reaction solution is poured into crushed ice,Extracted with dichloromethane (400 mL x 2)The combined organic phases were washed successively with saturated sodium bicarbonate solution (300 mL)And saturated brine (300 mL)Dried over anhydrous sodium sulfate,Concentrated under reduced pressure,To the residue was added anhydrous ethanol (500 mL) and stirred at 0 C for 30 minutes. The solid was collected by suction filtration,The title compound 9c was obtained as a white solid (129 g, 77%).

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, 1-Fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Gu Zheng; Wu Wuyong; Qu Tong; Tan Haoxiong; Kang Panpan; Deng Bingchu; (48 pag.)CN106892948; (2017); A;,
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Reference of 578-57-4,Some common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, molecular formula is C7H7BrO, 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: DMF (40 mL), NaI (375 mg, 2.5 mmol), and 1,2-dibromoethane (100muL, 1.16 mmol) were added to an undivided electrochemical cell, fitted with an iron/nickel (64/36) anode, and surrounded by a nickel foam as the cathode (surface: 40 cm2, porosity: 500 mum, Goodfellow).The mixture was electrolyzed under argon at a constant current intensityof 0.2 A at r.t. for 15 min. The current was then stopped, then NiBr2bpy (187 mg, 0.5 mmol) and aryl or heteroaryl halide (5 mmol),were sequentially added. The solution was electrolyzed at 0.2 A untilthe starting aryl or heteroaryl halide had been totally consumed (2-5h). Sat. aq EDTA-Na2 solution (50 mL) was added, and the resultingsolution was extracted either with EtOAc (for aryl halides) or withCH2Cl2 (for heteroaryl halides) (3 × 50 mL). The combined organic layerswere washed with brine (50 mL), dried (MgSO4), filtered, and concentratedunder vacuum. The crude product was purified by flashchromatography (silica gel, 70-200 mum).

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

Reference:
Article; Rahil, Rima; Sengmany, Stephane; Le Gall, Erwan; Leonel, Eric; Synthesis; vol. 50; 1; (2018); p. 146 – 154;,
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Application of 2752-17-2, These common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, 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.

H(5O,2)-CBZ; Several approaches were tried to synthesize the N,N,N’,N’-Tetrakis-(2-amino-ethyl)- 3-oxapentane- l ,5-diamine [H(5O,2)-amine]. It was found that the reaction of 5LIO-amine with CBZ-aziridine provides clean H(5O,2)-CBZ.; 5LIO-amine (0.21 g, 2 mmol) and CbZ-aziridine ( 1.77 g, 10 mmol) were mixed in tert- butanol (30 ml.) at room temperature under N2. The mixture was stirred under a N2 atmosphere at 8O0C for 16 hrs. when TLC showed the completeness of the reaction. The volatile were removed under vacuum and the residue was dissolved in dichloromethane. The appropriate fractions of a gradient flash silica gel column ( 1 -7% methanol in dicholoromethane) were collected and evaporated to dryness to give a pale beige thick oil, yield: 1.28 g, 79%.[0301] ‘ H NMR(300MHz, CDCl3): delta 2.53(s,br, 12H), 3.17(s,br, 4H), 3.83(s, br, 8H), 5.04(s, 8H), 7.29(s,br, 20H). 1 3C NMR (300MHz, CDCI3): delta 38.8, 53.0, 53.6, 69.3, 128.0, 128.1 , 128.4, 136.6, 156.4. MS(FAB+, DTT/DTE): 813.5 (MH+).

The synthetic route of 2752-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2008/8797; (2008); A2;,
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Related Products of 6096-89-5, The chemical industry reduces the impact on the environment during synthesis 6096-89-5, name is 2-(4-Fluorophenoxy)ethylamine, I believe this compound will play a more active role in future production and life.

2-(4-Fluorophenoxy)ethylamine (5A-1) in hydrochloride form is dissolved in wa- ter and basified with 1N sodium hydroxide (NaOH) to basic pH, and then extracted with ether. The free amine is thus obtained (yield = 74%).The malonate monoester (O) (7.5 g), the amine (5A)-1 (4.14 g) in ethanolic solution (30%) and hydroxybenzotriazole (HOBT) (3.97 g) in 70 ml of THF are placed in a 500 ml three-necked flask. After complete dissolution, the whole is cooled to -7C and DCC (5.5 g) diluted in 30 ml of THF is then added dropwise over 30 minutes.The mixture is allowed to warm to room temperature and is then left stirring for 19 hours. At room temperature, the medium becomes cloudy (white precipitate).The precipitate (dicyclohexyl urea) is filtered off and concentrated to dryness. 15.77 g of a beige-coloured solid are obtained.This crude solid is taken up in ethyl acetate (400 ml) and washed with:- HCMN (150 ml)- saturated sodium hydrogen carbonate solution (NaHCO3) (150 ml)- saturated NaCI solution (150 ml) – water (150 ml).After drying over MgSO4 and evaporating off the solvent, 9.34 g of a beige-coloured solid are obtained.YId: 84% m.p. = 1200C 1H NMR (DMSO delta in ppm): 1.08 (s, 3H); 3.41 (t, 2H); 3.93 (t, 2H); 4.07 (q, 2H);6.89 (t, 2H); 7.08 (t, 2H); 7.31 (s, 4H); 7.83 (s, 1H); 8.60 (t, 1H).Purity = 67%MS (APCI) m/z: 419 [M+H]+

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-(4-Fluorophenoxy)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; WO2008/6432; (2008); A1;,
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Reference of 22236-08-4, 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 22236-08-4 as follows.

Intermediate.11 rac-Allyl [l -{N’-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl} -3-(3,4-dichlorophenyl)-4,5- dihydro- l//-pyrazol-4-yl]carbamate To a stirred solution of m-difluoromethoxy aniline, 8.20 ml. (65.5 mmol) in anhydrous tetrahydrofuran (100 mL) at -78 C was added n -butyl lithium, 33.0 mL (65.5 mmol, 2 M in hexane) dropwise, while maintaining the reaction temperature below -65 C during the addition. The reaction mixture was stirred for 1 hour at -78 C before rac-phenyl 4-{[(ailyioxy)carbonyl]amino}-N-cyano-3-(3,4- dichlorophenyl)-4,5-dihydro- 1 H-pyrazole- 1 -carboximidate (intermediate 9), 10.0 g (21.8 mmol) in anhydrous tetrahydrofuran (600 mL) was added dropwise maintaining the reaction temperature below -65 C. The reaction mixture was stirred for 2 hours at -78 C before slowly pouring over saturated ammonium chloride solution (700 mL). The crude product was extracted into ethyl acetate (700 mL) and the organic layers were combined and washed with brine solution (350 mL). The collected organic phase was dried over magnesium sulfate, filtered and the solvent evaporated to yield an off-white crude solid. The crude solid was precipitated from a minimum volume of ethyl acetate, filtered, and washed with diethyl ether to yield rac-allyl [ 1 – {N’-cyano-N- [3 – (difluoromethoxy)phenyi]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazoi-4- yl] carbamate, 7.6 g (67%) as a white solid. NM R (400 MHz, DMSO-d6): delta [ppm] = 4.08 (dd, 1H), 4.36-4.53 (m, 3H), 5.11 (dd, 1H), 5.17 (dd, 1H), 5.50-5.59 (m, 1H), 5.77-5.90 (m, 1H), 6.99 (dd, 1H), 7.16 (t, 1H), 7.21 (t, 1H), 7.23 (dd, 1H), 7.39 (t, 1H), 7.73-7.81 (m, 2H), 8.15 (d, 1H), 8.17 (d, 1H), 9.79 (br s, 1H). I MS (method 3): Rt = 1.78 min MS (ESI): [M + Hf = 523.2

According to the analysis of related databases, 22236-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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Some common heterocyclic compound, 107622-80-0, name is (4-Phenoxyphenyl)methanamine, molecular formula is C13H13NO, 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. name: (4-Phenoxyphenyl)methanamine

General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 107622-80-0, its application will become more common.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
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171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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. Application In Synthesis of 3,5-Dimethoxyphenylacetylene

To a solution of 69 benzyl-3-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)azetidine-1-carboxylate 2e (0.123 g, 0.31 mmol), 43 1-ethynyl-3,5-dimethoxybenzene (0.740 g, 3.10 mmol) and 44 triethylamine (0.310 g, 3.10 mmol) in 32 N,N-dimethylformamide (5 mL), under nitrogen protection, were added 45 cuprous iodide (12 mg, 0.06 mmol) and 46 1,1?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (22 mg, 0.03 mmol). The mixture was heat to 80 C. and stirred for 5 h. The mixture was cooled to room temperature, quenched with saturated ammonium chloride solution (10 mL) and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with brine (20 mL×2), dried over anhydrous sodium sulfate and filtered. The residue was purified by preparative-TLC (19:1 dichloromethane/methanol) to provide 71 benzyl-3-(8-amino-1-((3,5-dimethoxyphenyl)ethynyl)imidazo [1,5-a]pyrazin-3-yl)azetidine-1-carboxylate2f (52.5 mg, 0.11 mmol, grey solid), yield: 35%.MS m/z (ESI): 484 [M+1].

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU INNOCARE PHARMA TECH CO., LTD.; KONG, Norman Xianglong; ZHOU, Chao; CHEN, Xiangyang; US2019/177333; (2019); 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. 109-85-3, name is 2-Methoxyethylamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H9NO

To a suspension of 43 (1.3 g, 3.26 mmol) in dry DCM (50 mL) at RT was added 2- methoxyethanamine (1.226 g, 16.32 mmol), acetic acid (0.98 g, 16.32 mmol) and sodium triacetoxyborohydride (3.46 g, 16.32 mmol), and the reaction mixture was stirred at RT for 24 hours. It was then diluted with additional DCM and washed with saturated NaHCO3 solution, dried OVCr Na2SO4, filtered and concentrated to dryness to afford 44 (1.5 g, 100% yield) as an yellow oil which was used crude in the next step with no additional purification MS (m/z): 458.2 (M+H)

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; METHYLGENE INC.; WO2009/109035; (2009); A1;,
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Electric Literature of 17061-62-0,Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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 solution of N,N-bis(4-methoxybenzyl)amine (Intermediate EEl 1; 200 g, 775.19 mmol) in DCM (2.5 L) was added Et3N (336.17 mL, 2325.5 mmol), andthe reaction mixture was cooled to 0 C. Ethanesulfonyl chloride ( 95 mL,1007.75 mmol) was added in drop-wise manner followed by DMAP (19.0 g,155.03 mmol). The resulting reaction mixture was stirred at ambient temperaturefor 30 mm. The reaction was monitored by TLC and upon completion, themixture was diluted with H20 and the layers were separated and the aqueousphase was extracted with DCM (3 x 1.5 L). The combined organic layer waswashed with H20, brine, and dried over Na2504. The solvent was removed under reduced pressure to afford the cmde material which was purified by column chromatography over 5i02 gel (100-200 mesh), eluting with a gradient of 0-12% EtOAc in hexane affording the title compound (145 g, 5 3.4%) as a white fluffy solid.

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

Reference:
Patent; AMGEN INC.; HARRINGTON, Paul E.; ASHTON, Kate; BROWN, Sean P.; KALLER, Matthew R.; KOHN, Todd J.; LANMAN, Brian Alan; LI, Kexue; LI, Yunxiao; LOW, Jonathan D.; MINATTI, Ana Elena; PICKRELL, Alexander J.; STEC, Markian M.; TAYGERLY, Joshua; (991 pag.)WO2018/183418; (2018); A1;,
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Synthetic Route of 592-55-2, 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. 592-55-2, name is 1-Bromo-2-ethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 15Production of Compound A-7In a 100 ml four-neck flask, 8.567 g (0.0400 mol) of 3-hydroxynaphthalic anhydride, 48.0 g of dimethyl sulfoxide, and 10.081 g (0.0730 mol) of potassium carbonate were put and stirred, and the atmosphere in the system was replaced with nitrogen gas. Dropwise added was 11.233 g (0.0734 mol) of bromoethyl ethyl ether, and the resultant was stirred at 70 C. for 5 hours. In the reaction liquid, 12 ml of deionized water and 9.6 ml of 48% by weight aqueous sodium hydroxide solution were put, stirred at 50 C. for 2 hours, and thereafter ice-cooled, and 21.0 g of 35% by weight aqueous hydrochloric acid solution was put and stirred at 60 C. for 2 hours. The reaction liquid, 500 ml of methylene chloride, and 200 ml of deionized water were added and subjected to oil-water separation to yield the organic layer, which was washed three times with 200 ml of deionized water and thereafter concentrated, and the organic layer was concentrated and subjected to purification by silica gel chromatogram (developing solvent with a hexane-to-ethyl acetate volume ratio of 2 (hexane):3 (ethyl acetate)) to yield the compound A-7 which was a target as a pale yellow solid. Yield: 5.20 g (yield: 45.4%), purity: 98.3% by HPLC (column: Inertsil ODS-2 manufactured by GL Sciences Inc., 4.6 mm×250 mm, solvent: acetonitrile/water=7/3, L-7455 diode array detector manufactured by Hitachi, Ltd., detection wavelength: 230 nm). The measurement results of 1H-NMR by a deuterated dimethyl sulfoxide solvent are listed in Table 1-3.

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

Reference:
Patent; Murai, Toshihiko; Makabe, Yoshie; Fujita, Shohei; US2012/289697; (2012); A1;,
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