Category: ethers-buliding-blocks

These common heterocyclic compound, 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)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. Product Details of 175278-09-8

4-Bromo-2-trifluoromethoxy-phenylamine (13 g, 0.05 mol) and But-2-ynedioic acid diethyl ester (10.3 g, 0.12 mol) were dissolved in EtOH (120ml) in a 500 ml round bottom flask and refluxed. The reaction was monitored by LC-MS. 3 h later; 0.3 eq. but-2-ynedioic acid diethyl ester was added. At t = 5h, the reaction mixture was concentrated down to remove the solvent under vacuum, a thick oil was obtained and was used without purification for the next step. MS [M+H]+ = 426.

The synthetic route of 4-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong, R.; DU, Zhimin; JI, Mingzhe; JIN, Haolun; KIM, Choung, U.; MISH, Michael, R.; PHILLIPS, Barton, W.; PYUN, Hyung-jung; SHENG, Xiaoning, C.; WU, Qiaoyin; ZONTE, Catalin, Sebastian; WO2011/156610; (2011); A2;,
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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. 7664-66-6, name is 4-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H13NO

Phenyl chloroformate (15.2 kg, 97.1 mol) was dissolved in toluene (115.7 kg) and cooled to 3 0C. 4-isopropoxyaniline (III) (13.3 kg, 88.0 mol) was mixed with acetonitrile (43.4 kg) and slowly added to the phenyl chloroformate solution over 1 hour 40 minutes, followed by slow addition of triethylamine (9.8 kg, 96.8 mol) over 46 minutes. The mixture was heated to 17.5 0C and stirred for 3 hours 30 minutes until the reaction was deemed complete by HPLC. The product solution was washed with IN HCl, followed by removing acetonitrile though an azeotropic distillation with additional toluene (52.3 kg). The solution was heated to 58 0C before slowly adding heptane (43.7 kg) over 1 hour 2 minutes, after which the slurry was cooled to 23.5 0C over 2 hours 35 minutes and stirred for an additional 2 hours 51 minutes. The material was isolated, washed twice with heptane, and dried at < 40 0C for 3 hours 49 minutes. The product was discharged, yielding 19.1kg of the title compound (HIa) (80% yield, 100% purity HPLC AUC). 1H NMR (300 MHz, CD3OD, delta): 7.38 (m, 4H), 7.19 (m, 3H), 6.86 (d, J = 9Hz 2H), 4.52 (sept, J = 6Hz, IH), 1.28 (d, J = 6Hz, 6H). 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 7664-66-6. Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC; ARMITAGE, Ian; BOURLAND, Michael, E.; BOYLE, Craig, J.S.; COOPER, Martin, Ian; FERDOUS, Abu, J.; LANGSTON, Marianne; WO2010/59239; (2010); A2;,
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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 5414-19-7 as follows. Product Details of 5414-19-7

Part F:; To a DMF (9 mL) solution of Part E (1.08 g, 2.71 mmol) was added K2CO3 (1.12 g, 8.16 mmol), 18-crown-6 (0.21 g, 0.80 mmol), and bis (2-bromoethyl) ether (0.37 mL, 2.9 mmol). The slurry was stirred at 60C for 72 hr. Additional bis (2-bromoethyl) ether was added at 24 hr (0.4 mmol) and 48 hr (1.2 mmol). The solvent was stripped in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was separated, dried over MgS04, and evaporated to an oil. Recrystallization from diethyl ether produced 0. 88 g (69 %) of the desired compound in the form of a white solid. LCMS: itvz = 469.2 (M+H).

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/42521; (2005); A2;,
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Electric Literature of 767-91-9, A common heterocyclic compound, 767-91-9, name is 2′-Methoxyphenyl acetylene, molecular formula is C9H8O, 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 mixture of aryl iodide (2 mmol), aryl alkyne (2.4 mmol), Ni(OAc) 2 (10 mol %), Et3N (6 mmol) and 1,4-dioxane (15 mL) were charged into the reactor (steel bomb). The reactor was closed and pressurized to ~2bar CO and then stirred at 100 C for 4 h. The reaction Progress was monitored by TLC. The reaction mixture was cooled to room temperature, before being filtered through a pad of Celite. The filtrate was concentrated and purified by silica gel with a mixture of hexane and ethyl acetate to give the pure product. For all examples, reactions were performed on 100 mg scale of corresponding aryl iodides.

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:
Article; Charugandla, Renuka; Vangala, Markandeya Sarma; Chidara, Sridhar; Korupolu, Raghu Babu; Tetrahedron Letters; vol. 59; 34; (2018); p. 3283 – 3287;,
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Related Products of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole (L1): A solution of 3,5-dimethyl-1H-pyrazole (0.30 g, 3.2 mmol) in DMF/THF (v/v = 1:1, 12 mL) was added to a suspension of NaH (0.15 g, 6.4 mmol) in DMF/THF (v/v = 2:1, 15 mL) and stirred at 60 ¡ãC for 2 h. Then, the resulting solution was added under stirring to a solution of 3-bromopropyl phenyl ether (0.70 g, 3.2 mmol) in DMF (7 mL). The mixture was allowed to stir for 24 h at 60 ¡ãC, cooled, and treated cautiously with H2O (5 mL) to decompose excess NaH. The solvents were then evaporated under reduced pressure. The residue was extracted with ethyl acetate (3 * 15 mL), washed with H2O (2 * 15 mL). The organic phase was dried over MgSO4 and filtered, before the solvent was evaporated under reduced pressure. After workup and purification by chromatographic column on silica gel (hexane/ethyl acetate, 90:10), L1 was obtained as a colorless oil (0.47 g, 64percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Bromopropoxy)benzene, its application will become more common.

Reference:
Article; Ulbrich, Ana H.D.P.S.; Campedelli, Roberta R.; Milani, Jorge L. Sonego; Santos, Joao H.Z. Dos; Casagrande, Osvaldo De L.; Applied Catalysis A: General; vol. 453; (2013); p. 280 – 286;,
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Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 111-95-5, Formula: C6H15NO2

EXAMPLE 61 Bis-(2-methoxy-ethyl)-prop-2-ynyl-amine Propargyl bromide (17.8 g, 150 mmol) was added dropwise to a mixture of bis(2-methoxy-ethyl)amine (20 g, 150 mmol) and cesium carbonate (49 g, 150 mmol) in 350 mL of acetone. The mixture was stirred overnight under nitrogen at room temperature. The inorganic salts were then filtered off, and the solvent was removed. The residue was dissolved in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were then evaporated to give 20 g of bis-(2-methoxy-ethyl)-prop-2-ynyl-amine: mass spectrum (m/e): M+H 172.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; American Cyanamid Company; US6297258; (2001); B1;,
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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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-4-methoxynaphthalene

2-(4-Methoxy-1-naphthyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (S2). 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (1.92 mL, 15.00 mmol) was added dropwise to a solution of 1-bromo-4-methoxynaphthalene S1 (1.19 g, 5.00 mmol), NEt3 (2.79 mL, 20 mmol) and Pd(ddpf)Cl2.CH2Cl2 (510 mg, 0.625 mmol) in anhydrous dioxane (15 mL) and the reaction mixture heated at 100 C. for 23 h. After cooling to room temperature, the reaction was quenched cautiously with water (20 mL) and extracted with CH2Cl2 (3¡Á35 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2; EtOAc/heptane; 0-30%) afforded the pinacol ester as an off-white solid (1.09 g, 77%). 1H NMR (400 MHz, CDCl3) delta=1.41 (s, 12H), 4.02 (s, 3H), 6.82 (d, J=7.8 Hz, 1H), 7.43-7.48 (m, 1H), 7.53-7.57 (m, 1H), 8.04 (d, J=7.8 Hz, 1H), 8.28 (dd, J=0.9, 8.3 Hz, 1H), 8.75 (d, J=8.3 Hz, 1H). 13C NMR (100 MHz, CDCl3) delta=25.1, 55.6, 83.5, 103.3, 122.1, 125.0, 125.5, 127.0, 128.3, 137.0, 138.3, 158.3. HRMS (ESI+) (m/z): [M+H]+ calcd. for C17H22BO3, 285.1657; found, 285.1643.

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 5467-58-3.

Reference:
Patent; Hadjifrangiskou, Maria; Almqvist, Fredrik; Shaffer, Carrie L.; Good, James; (66 pag.)US2017/233409; (2017); A1;,
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Related Products of 1978-39-8,Some common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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 compound Al (400 rng, 0.53 mrnoi) and 5-fluoro-2-rnethoxyaniline (150,7mg, 1.07 mmoi) intoluene (10 rnL) was added Ti(O-i] r)4 (151.6 mg, 0.53 mmoi). Themixture was stirred at 120 C over night under N2. The mixture was quenched with [120 (50 rnL) and extracted with DCM (20 mL x 3). The combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by silica gel column chromatography (DCMMeOH = 15/i) to afford the crude products 29-1 and 29-2 (320 mg) as a yellow solid. LC-MS: m/z 89.4 [M+I-[. To a solution of compounds 29-1 and 292 (310 ing, 0.35 rnrnol) in DCM (5 mL) was added DAST (56.2mg, 0.35 mmoi) at -78 C underN2. After stirred at -78 C for 2 h, the mixture was quenched with aqueous NaHCO3 and 1-120 and then extracted with DCM (30 rnL x 3. The combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by prep-HPLC to afford compound 29 (53 rng, yield17.5%) as white solid. Partial ?HNMR (CDC13, 400 MHz): 6.756.7I (m, 2H). 6.64-6.59 (rn, 2H), 4.89 (s, IH), 4.76-4.72 (rn. 1H), 4.43 (d, J= 8.0 Hz, IH), 4.34-4.30 (rn, TH), 3.87 (s. 3H). 2.59-2.50 (m, 21-1), LG-MS: m/z 871.4 [M¡ÀH.

The synthetic route of 1978-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGRIMETIS, LLC; CALABRESE, Andrew; (110 pag.)WO2018/132288; (2018); A1;,
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Application of 171290-52-1, 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 171290-52-1 as follows.

To a mixture of compound 97 (6.78 g), compound 98 (10.0 g), cuprous iodide (340 mg), bistriphenylphosphine palladium dichloride (1.25 g) and triethylamine (14.7 mL) at room temperature DMF, nitrogen replacement three times, rise to 80 and stir overnight, add water, extract with ethyl acetate, the extract was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, the solvent was removed, the residue was separated by column chromatography, Target product (10.5g).

According to the analysis of related databases, 171290-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shou Yao Konggu (Beijing) Co., Ltd.; Wang Jinghan; Yao Jinsuo; Duan Xiaowei; Yuan Baokun; Sun Ying; Lu Chang; (42 pag.)CN110950867; (2020); A;,
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Application of 31576-51-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 31576-51-9 name is 2-(2-Methoxyethoxy)ethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(i) 3-Ami no-5-bromo-N-(2-(2-methoxyethoxy)ethyl)benzamideA stirred mixture of 3-amino-5-bromobenzoic acid (800 mg, 3.59 mmol), 2-(2- methoxyethoxy)ethanamine (856 mg, 7.18 mmol) and Et3N (1.5 mL, 10.76 mmol) in DCM (13mL) was cooled in an ice bath. T3P (50 w/w in EtOAc, 3.2 mL, 5.38 mmol) was added dropwise, the ice bath was removed and the reaction mixture allowed to warm to room temperature. DMF (2 mL) was added to aid solubility and the reaction stirred at room temperature overnight. The reaction mixture was partitioned between sat. aq. NaHCO3 (50 mL) and DCM (50 mL). The aqueous phase was back extracted with fresh DCM (50 mL).The combined organic extracts were washed with water (100 mL), brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to afford an orange oil. The crude product was purified by chromatography on silica gel (40 g column, 0-5% MeOH) to afford the sub-title compound (880 mg) as an orange oil.1H NMR (DMSO-d6) 400 MHz, O: 8.36 (t, 1H), 7.07 (t, 1H), 7.00-6.99 (m, 1H), 6.84 (t, 1H),5.57 (s, 2H), 3.53-3.48 (m, 4H), 3.44-3.42 (m, 2H), 3.35 (q, 2H), 3.23 (s, 3H). LCMS m/z 317/319 (M¡ÂH) (ES)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Methoxyethoxy)ethanamine, and friends who are interested can also refer to it.

Reference:
Patent; TOPIVERT PHARMA LIMITED; RESPIVERT LIMITED; FYFE, Matthew Colin Thor; WO2014/162121; (2014); A1;,
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