Tag: M.W=200-300

168971-68-4, The chemical industry reduces the impact on the environment during synthesis 168971-68-4, name is 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

Step 3: (1 -benzyl-3-(2-fluoro-4-(trifluoromethoxy)phenyl)-4-methyl-5-(trifluoromethyl)-1 H-pyrrol2-yl)(morpholino)methanone (SC-262)Under an nitrogen atmosphere (1 -benzyl-4-methyl-3-(4,4,5, 5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-5- (trifluoromethyl)-IH-pyrrol-2-yl)(morpholino)methanone (50 mg, 0.106 mmol) was dissolved in DMF (0.5 mL) and LiOH (2 mg, 0.106 mmol), bis(tri-tert-butylphosphine)palladium (0) (3 mg, 0.007 mmol) and 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene (24 mg, 0.096 mmol) were subsequently added. The reaction mixture was stirred at 80C under microwave irridation for I h. The mixture was cooled to RT and the reaction was stopped by addition of 1 M NaOH solution (2 mL). The crude product was extracted with EtOAc (2×3 mL) and the combined organic layers were washed with water (3×1 mL), dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude mass was purified by flash chromatography to give SC-262 (34 mg, 66.8 %).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; WO2014/32801; (2014); A1;,
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19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline, A new synthetic method of this compound is introduced below.

To a solution of 4-bromo-3-methoxyaniline (5.7 g, 28.2 mmol) in toluene (100 mL) and water (10 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-lH-pyrazole-l-carboxylate (9.96 g, 33.9 mmol), potassium phosphate (8.98 g, 42.3 mmol) and PdCl2(dppf)-DCM (1.152 g, 1.411 mmol) at RT. The reaction was stirred under argon at 95 ¡ãC for 2.5 hrs and then was cooled to RT. The reaction mixture was diluted with EtOAc, washed with H20, saturated aHC03 and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by normal phase chromatography to give Intermediate 1 as light tan solid (5.1 g, 63percent yield). LCMS (ESI) m/z: 290.1 (M+H)+; XH NMR (400MHz, chloroform-d) delta 8.35 (d, J=0.5 Hz, 1H), 8.01 (s, 1H), 7.29 (d, J=8.0 Hz, 1H), 6.37 – 6.26 (m, 2H), 3.84 (s, 3H), 3.79 (br. s., 2H), 1.66 (s, 9H).

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; BRISTOL-MYERS SQUIBB COMPANY; HU, Zilun; QUAN, Mimi L.; WO2014/134391; (2014); 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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 51388-20-6

Preparation XXVIII Methyl 2-methyl-2-[[4-(phenylmethoxy)phenyl]amino]propionate 3 g (15 mmol) of 4-(phenylmethoxy)aniline and 5.5 g (30 mmol) of methyl 2-bromo-2-methylpropionate are mixed and 1.95 g of sodium bicarbonate are added. The reaction medium is stirred for 5 h at 140 C. and then cooled and taken up with 50 ml of water and 100 ml of ethyl ether. The aqueous phase is separated off and re-extracted with 50 ml of ethyl ether and the combined organic phases are washed with water and then dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (8/2; v/v) as the eluent to give the expected product in the form of a beige crystalline solid (yield=75%). M.p.<50 C. The synthetic route of 51388-20-6 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Binet, Jean; Boubia, Benaissa; Chaput, Evelyne; Edgar, Alan; Ou, Khan; Ratel, Philippe; Samreth, Soth; Thomas, Didier; US2006/25589; (2006); A1;,
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These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)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. 54314-84-0

To a solution of Lambda/-[4-(7-Hydroxy-6-methoxy-quinoIin-4-yloxy)-phenyl]-benzamide (0.12g, 0.32mmol) in DMF (3ml) was added potassium carbonate (0.11g, O.deltammol, 2.5eq) and benzyl 3- bromopropyl ether (64ul, 0.36mmol, 1.1 eq). The reaction wasstirred at room temperature for 48 hours. The DMF was removed under reduced pressure and ethyl acetate was added to the crude residue, washing with water. The ethyl acetate layer was dried over magnesium sulphate and evaporated under reduced pressure. The product was purified by column chromatography, eluting with ethyl acetate/heptane (2:1 ) to yield the title compound (0.15g, 90percent) as a yellow solid, m/z 535 [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 54314-84-0.

Reference:
Patent; CHROMA THERAPEUTICS LTD; WO2006/117570; (2006); A1;,
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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. 29578-83-4 name is 1-Bromo-3-methoxy-5-methylbenzene, 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. 29578-83-4

Synthesis of 5-(1-(3-methoxy-5-methylphenyl)cyclohexyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (3) A solution of 1-bromo-3-methoxy-5-methylbenzene (2, 8.0 g, 39.80 mmol) in tetrahydrofuran (20 mL) was added dropwise to a flask containing Mg turnings (1.36 g, 55.72 mmol) in tetrahydrofuran (30 mL). Catalytic iodine was added to the mixture and refluxed the reaction for 2 h. To a solution of 5-cyclohexylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (1, 8.0 g, 35.71 mmol) in tetrahydrofuran (50 mL) at 0 C., freshly prepared (3-methoxy-5-methylphenyl)magnesium bromide was added slowly. The reaction was allowed to stir at room temperature for 12 h. On completion, the reaction mixture was quenched with 1 M hydrochloric acid and extracted with ethyl acetate (100 mL). The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 5-(1-(3-methoxy-5-methylphenyl)cyclohexyl)-2,2-dimethyl-1,3-dioxane-4,6-dione as a colorless liquid. Yield: 8.0 g, crude; MS (ESI) m/z 347.12 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-methoxy-5-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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Adding some certain compound to certain chemical reactions, such as: 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, 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 3401-47-6. 3401-47-6

2-Methoxynaphthalene-1-thiol (compound 11r) was prepared as follows. (Preparation of (2-methoxynaphthalen-1-yl)magnesium bromide) A THF solution (8 mL) of 1-bromo-2-methoxynaphtalene (4 g, 16.87 mmol) was added, dropwise, to a THF slurry (17 mL) of magnesium turnings (533 g, 21.93 mmol) that had been previously activated through the addition of 1,2-dibromoethane (150 muL, 1.69 mmol). The flask was gently heated with a heat gun, while avoiding boiling. After 30 min, the flask was irradiated at rt in an ultrasonic cleaning bath for 2.5 h to afford a THF solution of the Grignard reagent. Elemental sulfur (0.757 g, 23.62 mmol) was added in one portion, under a N2 blanket, to the 0 C. solution of (2-methoxynaphtalen-1-yl)magnesium bromide (vide supra). After 30 min, lithium aluminum hydride powder (0.32 g, 8.44 mmol) was added in very small portions. After 30 min, the reaction was diluted with cold, aqueous, saturated NH4Cl (20 mL) and then aqueous citric acid 2M (5 mL). The mixture was extracted with dichloromethane (3¡Á30 mL) and, after the removal of volatiles, the resulting slightly yellow solid was partially dissolved with pentane. The pentane solution was cooled by immersion into a -78 C. cooling bath and after 5 min the temperature was raised to 0 C. After 15 min the solution was filtered to afford 3.01 g (94%) of compound 11r as a white crystalline solid: Mp 66-67 C. (lit. 65-68 C.). 1H NMR (400 MHz, Chloroform-d) delta 7.98 (dd, J=8.5, 0.9 Hz, 1H), 7.74 (d, J=8.2 Hz, 1H), 7.61 (d, J=9.0 Hz, 1H), 7.49 (ddd, J=8.4, 6.8, 1.3 Hz, 1H), 7.34 (ddd, J=8.0, 6.8, 1.1 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 4.39 (s, 1H), 3.95 (s, 3H); 13C NMR (100 MHz, Chloroform-d) delta 151.51, 132.01, 129.28, 128.43, 126.64, 126.28, 124.04, 123.98, 114.72, 112.71, 56.82; IR (ATR) 3052, 2937, 2838, 2579, 1506, 1265, 1247, 1075, 797, 767, 741 cm-1; HRMS calculated for C22H18O2S2 (disulfide) 401.0640. found 401.0648 (M+Na)+

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 1-Bromo-2-methoxynaphthalene.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY GHOST; FLEMING, FRASER FERGUSSON; Lujan-Montelongo, Jesus Armando; US2015/239833; (2015); 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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 103291-07-2

Under a nitrogen atmosphere, 4-fluoro-3-methoxybromobenzene (163 mg) was added dropwise to a THF suspension of magnesium (23 mg) and iodine (catalytic amount). After heating under reflux,After stirring at room temperature for 30 minutes, {(5S) -2-oxo-5- (propan-2-yl) -3- [6- (trifluoromethyl) pyridin-3-yl] imidazolidin-1-yl} acetaldehyde A THF solution of (50 mg) was added dropwise. After stirring at room temperature for 2 hours,A saturated ammonium chloride aqueous solution was added, and the mixture was extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was purified by preparative HPLC.DMSO (2 mL) of the obtained product2-iodoxybenzoic acid (27 mg) was added to the solution,Stir overnight at room temperature. After adding water and filtering through Celite,The filtrate was extracted with chloroform. After concentrating the organic layer under reduced pressure,The residue was purified by PTLC (silica gel, hexane / ethyl acetate = 1: 1),The title compound (24 mg) was obtained.

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co Ltd; Moriya, Minoru; Yamamoto, Shuji; Abe, Kimiyoshi; Ota, Hiroyuki; Sun, Ziang Min; Wakasugi, Daisuke; Araki, Hiroko; (49 pag.)JP2015/157764; (2015); A;,
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Some common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, molecular formula is C11H16O4, 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. 35896-58-3

Compound 3 (0.32 g, 1.5 mmol) was dissolved in acetonitrile (2 mL), and an excess of asolution of K2S2O8 (1.6 g, 6 mmol) in 3mL water was added at 25 C. The reactionmixture was stirred at room temperature for 1 h. The progress of the reaction was monitoredby TLC. After completion of the reaction, the mixture was extracted withdichloromethane (10mL 3). The organic layers were washed with brine until neutrality,then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude productwas purified by a silica-gel column chromatography with petroleum ether and EtOAc(3:1) to give CoQ0, 0.26 g, 96%, red needles, m.p 56-57 C (lit5 57-59 C). IR: (cm1)3590, 3415, 1661, 1603, 1291, 1226, 999. 1H NMR (400 MHz, CDCl3) d 6.44 (q,J1.7 Hz, 1H), 4.02 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 2.04 (d, J1.6 Hz, 3H,CH3). 13C NMR (101 MHz, CDCl3) d 184.4 (C5O), 184.2(C5O), 145.0, 144.8, 144.0,131.2, 61.2 (OCH3), 61.1 (OCH3), 15.4 (CH3). GC-MS (EI): m/z 182. The spectroscopicdata are in accord with the literature

The chemical industry reduces the impact on the environment during synthesis 1,2,3,4-Tetramethoxy-5-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Qiu, Yong-Fu; Yan, Yi-Yu; Lu, Bin; Tang, Lei; Zhai, Yu-Lin; Chen, Ke-Xin; Wang, Jin; Organic Preparations and Procedures International; vol. 51; 6; (2019); p. 602 – 605;,
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402-07-3, 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 402-07-3 as follows.

To a solution of 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (69.0 mg, 0.27 mmol) in dry THF (4 mL) at -78 C under N2 was slowly added N-BuLi (0.11 mL, 2.5 M in N-pentane, 0.27 mmol). After being stirred for 30 min, a solution of 8 (50 mg, 0.11 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4Cl (15 mL) solution, and extracted with EtOAc (10 mL ¡Á 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtOAc/petroleum ether, Rf = 0.2) to give 25 (56 mg, 81%) as a pale brown solid. mp 34.7-36.7 C; 1H NMR (400 MHz, CDCl3) delta 0.001 (s, 3H), 0.07 (s, 3H), 0.83 (s, 9H), 2.41 (s, 3H), 2.94 (d, J = 4.0 Hz, 1H), 3.73 (s, 3H), 4.43 (d, J = 12.0 Hz, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.81-5.84 (m, 2H), 6.10 (t, J = 3.2 Hz, 1H), 6.34 (d, J = 3.6 Hz, 1H), 6.66 (dd, J = 3.6, 2.0 Hz, 1H), 6.99 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24 (d, J = 3.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H) ppm; 13C NMR (CDCl3, 100 MHz) delta -5.71, -5.67, 18.53, 21.56, 25.92, 25.92, 25.92, 53.27, 55.53, 62.79, 106.87, 106.91, 108.05, 108.43, 111.37, 117.21, 117.25, 121.56, 123.91, 126.96, 127.01, 127.35, 128.40, 129.44, 129.87, 134.75, 134.76, 135.81, 136.29, 145.17, 156.02 ppm; HRMS (M + Na+) calcd. for C31H37F3N2NaO5SSi 657.2042, found 657.2040; IR (KBr) 3383, 3146, 2956, 2929, 2857, 1734, 1594, 1465, 1415, 1377, 1329, 1241, 1175, 1123, 1032, 841, 778, 670 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 402-07-3, and friends who are interested can also refer to it.

Reference:
Article; Cheng, Chunwei; Liu, Yan; Song, Hao; Pan, Lili; Li, Jerry; Qin, Yong; Li, Rongshi; Marine Drugs; vol. 11; 8; (2013); p. 2927 – 2948;,
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7025-06-1, The chemical industry reduces the impact on the environment during synthesis 7025-06-1, name is 1-Bromo-2-phenoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: Toasolutionofbromide12(a-c)(0.3mmol)and bis(triphenylphosphine)palladium(II)dichloride(9mumol),N-ethyl-N-isopropylpropan-2-amine(0.3mmol)andcopper(I)iodide(0.03mmol)inDMF(1.5ml)wasaddedtheappropriatealkynerelatedalkyne(0.45mmol)andthevesselwasflushedwithargon,sealedandheated(70¡ãC,overnight).Theresultingdarkmixturewascooledtoroomtemperatureandpurifiedbysilicagelchromatographytoafford13(a-d).

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

Reference:
Article; Zhao, Xue Zhi; Hymel, David; Burke, Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 20; (2016); p. 5009 – 5012;,
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