Ethers-buliding-blocks

Electric Literature of 886762-08-9, These common heterocyclic compound, 886762-08-9, name is 5-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.

General procedure: A solution of substituted anilines (12.4 mmol) dissolved in 30 mL anhydrous THF was added very slowly into a stirred solution of triphosgene (1.40 g, 4.80 mmol) in 20 mL of THF. After stirringfor 15 min, triethylamine (2.90 mL, 20.6 mmol) was then added slowly to the reaction mixture. Stirring was continued for 20 min, various aromatic heterocyclic amines (12.0 mmol) in anhydrous THF (20 mL) was added directly to the above residue. After completion of the action, the reaction was quenched with dilute NaHCO3 and the solvent was subsequently removed in vacuo and extracted with ethyl acetate (3 30 mL). The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silicagel flash chromatography (PE/AcOEt = 5:1) gave as white solid (3a-3h) (yield: 30-50%).

Statistics shows that 5-Bromo-2-(trifluoromethoxy)aniline is playing an increasingly important role. we look forward to future research findings about 886762-08-9.

Reference:
Article; Shan, Yuanyuan; Wang, Chen; Zhang, Lin; Wang, Jinfeng; Wang, Maoyi; Dong, Yalin; Bioorganic and Medicinal Chemistry; vol. 24; 4; (2016); p. 750 – 758;,
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Some common heterocyclic compound, 2734-70-5, name is 2,6-Dimethoxyaniline, molecular formula is C8H11NO2, 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. SDS of cas: 2734-70-5

[015581 3-isothiocyanato-2,4-dimethoxypyridine, Example 771.1. A 2L round bottom flask was charged with 1,1?-thiocarbonyldi-2(1H)-pyridone (47.0 g, 202 mmol) and dissolved in dry DCM (405 mL). To that solution was added 2,6- dimethoxyaniline (31 g, 202 mmol) dissolved in DCM (405 mL) via an addition funnel at RT over 40 minutes. After 16 hours, the reaction was concentrated in vacuo and purified on silica gel (0-20percent EtOAc in heptanes) to give 2-isothiocyanato-1,3-dimethoxybenzene (32 g, 164 mmol, 81 percent yield). LCMS-ESI (POS.) mlz: 197.1 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2734-70-5, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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Related Products of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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 2.73 mmol appropriate alkyl halide (i.e., 17a-c, or18a-c), 0.6 g K2CO3 (4.34 mmol), and 0.6 g NaI (4.00 mmol) in ACN(12 mL) was mixed for 5 min in a 30 mL microwave reaction vessel.Then, 8.2 mmol appropriate amine derivative (i.e., 1-6, as shown inScheme 3) was added and the resulting content was mixed foradditional 2 min. The reaction vessel was capped, and insertedinside the microwave instrument (i.e., A CEM Model Single ModeMicrowave Instrument) and heated for 32 min at 105 C at thedynamic mode of the instrument automatically calibrating theradiation and temperature balance with respect to the change inpressure. Then, acetonitrile was distilled out under vacuum andthe residue thus obtained was mixed with 20 mL of K2CO3 solution(5.0%) and this mixture was heated at 60 C for 1 h. Then the mixturewas cooled down to room temperature and the aqueous phasewas extracted 3 times with 20 mL of ethylacetate. Combinedorganic extracts were dried over MgSO4 and concentrated underreduced pressure to give the product (i.e., free base). The free basewas dissolved in 10 mL acetone and HCl gas was continuouslypassed until HCl salt precipitation took place.

Statistics shows that 1-(3-Methoxyphenyl)-N-methylmethanamine is playing an increasingly important role. we look forward to future research findings about 41789-95-1.

Reference:
Article; Gulcan, Hayrettin Ozan; Unlu, Serdar; Esiringu, Ilker; Ercetin, Tugba; Sahin, Yasemin; Oz, Demet; Sahin, Mustafa Fethi; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5141 – 5154;,
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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 1462-37-9 as follows. Recommanded Product: ((2-Bromoethoxy)methyl)benzene

To a suspension of NaH (13.0 g, 0.32 mol) in THF (70 mL) was added malonic acid diethyl ester (51.9 g, 0.32 mol) drop wise at 0°C. When no more gas was formed reagent 1 (57.2 g, 0.27 mol) was added. The mixture was stirred at 75°C for 5 h. The mixture was allowed to reach room temperature and then quenched with water (300 mL). The mixture was extracted with MTBE (250 mL x 3). The combined organic layers were dried over MgS04 and evaporated to dryness. Flash chromatography (silica, petroleum ether: EtOAc 20:1 to 10:1 ) gave reagent 2 as a colorless oil (69.6 g, 74percent). 1H NMR (CDCI3) delta 7.24-7.34 (m, 5 H), 4.42 (s, 2 H), 4.10-4.22 (m, 4 H), 3.57 (t, J = 7.2 Hz, 1 H), 3.51 (t, J = 6.4 Hz, 1 H), 3.33 (s, 1 H), 2.17- 2.22 (m, 2 H), 1 .20-1.28 (m, 6 H).

According to the analysis of related databases, 1462-37-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; ESKILDSEN, J°rgen; WO2014/49133; (2014); 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 2062-98-8 as follows. name: Perfluoro(2-methyl-3-oxahexanoyl) fluoride

Under a nitrogen atmosphere, ethyl 3-dimethylam- inoethyl acrylate (1.43 g) was dissolved in toluene (10 ml), and pyridine (0.8 g) was added at room temperature. Perfluoro(1 -(1 -propoxy) propionic acid) fluoride (perfluoro(2- methyl-3-oxa-hexanoyl) fluoride) (3.2 g) was dropwise added thereto, followed by stirring for 10 hours at the same temperature. Water (20 ml) was added to the reaction mixture, and the organic phase was separated. Further, the aqueous phase was extracted with toluene (10 ml), and the extract was combined with the previous organic phase. This organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled oil to obtain 4.5 g of a compound represented by the following formula.

According to the analysis of related databases, 2062-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASAHI GLASS COMPANY, LIMITED; MORIZAWA, Yoshitomi; TAKAHIRA, Yusuke; (32 pag.)US2016/295864; (2016); A1;,
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Application of 36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

To a solution of 1-pyrazol [1,5-b] [PYRIDAZIN-3-YLETHANONE] (8.5 g, 52.7 [MMOL)] in DMF (100 mL) was added [DIMETHYLFORMAMIDE] di-tert-butylacetal (16.1 g, 79.2 [MMOL).] The reaction was heated at an oil bath temperature of 100 [C] for about 4 hours. The solvent was removed in vacuo. The residue was triturated with diethyl ether to give the title compound as a brown solid (8 g, 70%). 1H-NMR (300 MHz, [D6-DMSO) 6] 8.76 (dd, 1H, J = 10.0, 2. [0 HZ),] 8.74 (s, [1H),] 8.61 (dd, [1 H, J = 4.] 0,2. [0 HZ),] 7.74 (d, 1H, J = 12 Hz), 7.44 (dd, [1H,] J = 10.0, 4.0 Hz), 5.87 (d, [1H,] J = 12 Hz), 3.18 (bs, 3H), 2.97 (bs, 3H); MS [(ESI)] (M+H) [+] 217.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/35588; (2004); A1;,
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Related Products of 13070-45-6, A common heterocyclic compound, 13070-45-6, name is 6-Methoxy-1,2,3,4-tetrahydrocarbazole, molecular formula is C13H15NO, 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 stirred solution of acrylate 9 (1 mmol), cycloalkaneindole 10a,b, 11a-j, 12a,b, or 13a,b, (1 mmol), CsF (0.1 g), and hydroquinone (0.02 g) in DMF (1.5 mL) was heated at 120-140C for 4 h. The solvent was removed in vacuo (3 Torr), the residue was extracted with dichloromethane, the solvent was removed in vacuo. Column chromatography of the residue (silica gel (60 mesh), elution with methanol-chloroform, 1 : 10) afforded target compounds. This procedure was applied for the synthesis of the following compounds: 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2,3dihydro-1H-cyclopenta[b]indol-4-yl)propan-1-one hydrochloride (14a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(7-methyl-2,3-dihydro-1H-cyclopenta[b]indol-4-yl)propan-1-one (14b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15c), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15d), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-trifluoromethoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15e), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15f), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3,6-dimethyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15g), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6-fluoro-3-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15h), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3-methyl-6-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15i), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(3methyl-6-trifluoromethoxy-1,2,3,4-tetrahydrocarbazol-9-yl)propan-1-one (15j), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(7,8,9,10-tetrahydro-6H-cyclohepta[b]indol-4-yl)propan-1-one (16a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2-methyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]indol-4-yl)propan-1-one (16b), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)propan-1-one (17a), 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]-3-(2-methyl-6,7,8,9,10,11-hexahydrocycloocta[b]indol-5-yl)propan-1-one (17b).

The synthetic route of 13070-45-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bachurin; Sokolov; Aksinenko; Epishina; Goreva; Gabre?yan; Grigo?ev; Russian Chemical Bulletin; vol. 64; 6; (2015); p. 1354 – 1361; Izv. Akad. Nauk, Ser. Khim.; 6; (2015); p. 1354 – 1361,7;,
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24988-36-1, name is 1,5-Dibromo-2,4-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. category: ethers-buliding-blocks

4,6-Dimethoxy-1,3-dibromobenzene21 (1.50 g, 5.07 mmol) was added to a solution of i-PrMgCl (1 M in THF, 7 mL, 7 mmol) at -10 C under N2 atmosphere. After 45 min, methyl iodide (0.5 mL, 7.7 mmol) was added drop wise, and the mixture was allowed to stir at the same temperature for 30 min and then at rt for 4 h. The reaction was quenched by the addition of 10% HCl (15 mL). THF was removed in vacuum, and the mixture was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*30 mL) and brine (20 mL), dried (Na2SO4), filtered, and concentrated. The resulting crude compound was purified by column chromatography to get 8 (950 mg, 81%) as a colorless liquid. Rf 0.6 (1:10 ethyl acetate:hexane); numax (film) cm-1 1555, 1222, 1143, 1045; 1H NMR (CDCl3, 500 MHz): delta 7.24 (s, 1H, C6-H), 6.42 (s, 1H, C3-H), 3.87 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 2.1 (s, 3H, CH3); 13C NMR (CDCl3,125 MHz): delta 157.8 (C), 154.6 (C), 133.8 (CH), 120.0 (C), 100.8 (C), 96.2 (CH), 56.3 (CH3), 55.5 (CH3), 15.1 (CH3); HRMS (EI+) m/z 229.9946 ([M]+ C9H11BrO2, requires 229.9942).

The synthetic route of 24988-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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Electric Literature of 20781-20-8, A common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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: The 6-chloronicotinic acid (2g, 12.73 mmol) was dissolved inDMF (20 ml). In the prepared solution, TBTU (4.90 g, 15.28 mmol)and TEA (2.66 mL, 19.10 mmol) was added. The reaction mixture was stirred for 30 min at room temperature. An amine(12.73 mmol) was added and stirred for 3 h at room temperature.The progress of the reaction was monitored by TLC. The reactionmixture was then quenched with crushed ice (50g) and stirred for30 min. The obtained precipitate was filtered and dried. Finally the product was purified by column chromatography using ethyl acetate:petroleum ether as eluent. Yield: (2a:87%, 2c:86%, 2l: 88%).

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

Reference:
Article; Thirunavukarasu, Jayaprakash; Begam, Rosina; Shajahan; Journal of Molecular Structure; vol. 1196; (2019); p. 518 – 526;,
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Synthetic Route of 126829-31-0,Some common heterocyclic compound, 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, 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: A THF solution (0.2 mL) of PdCl2(MeCN)2 (3.9 mg, 0.015 mmol) and 2b (10.2 mg, 0.015 mmol) was stirred for 10 min. To the solution were added diiodoparacyclophane 6 (0.05 mmol) in THF (0.8 mL), i-Pr2NH (0.2mL), alkyne 7 (0.2 mmol) and CuI (2.9 mg, 0.015 mmol) in order. The resulting mixture was stirred at room temperature. After the reaction was complete, H2O was added to the reaction mixture, and organic materials were extracted with AcOEt. The organic layer was washed with brine and dried with Na2SO4. The solvent was removed under reduced pressure, and the crude products were purified by thin-layer chromatography to give dialkynylated product 8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Ethynyl-1,3-dimethoxybenzene, its application will become more common.

Reference:
Article; Kanda, Kazumasa; Oshima, Shoya; Shizuno, Tsubasa; Hamanaka, Risa; Fukai, Miku; Shibata, Takanori; Heterocycles; vol. 8; 2; (2014); p. 1355 – 1370;,
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