* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Trifluoro-acetic acid (5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester[ No CAS ]
With exclusion of oxygen, 350 mg [1.44 mmol] of (3-bromo-2,6-dimethylphenyl)acetic acid, 198 mg [0.43 mmol] of <strong>[25776-12-9]sodium tetrakis(4-fluorophenyl)borate</strong> dihydrate and 4.6 mg [0.014 mmol] of n-tetrabutylammonium bromide are suspended in a mixture of 268 mg [3.02 mmol, 45% strength] of sodium hydroxide solution, 405 mg of n-butanol and 2 g of water under argon. 1.53 mg of palladium on carbon [10%] are added, and the reaction mixture is stirred at 90 C. for 12 hours. After the reaction has ended (monitored by GC), the reaction mixture is cooled to RT and 1 g of water and 20 g of ethyl acetate are added. The pH of the mixture is adjusted to 1.5 using 32% strength hydrochloric acid and the mixture is then filtered through Celite. The organic phase is separated off and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried and concentrated. This gives a white solid which, according to GC-MS, has the following composition; 1.6% of 4,4'-difluorobiphenyl, 0.78% of (2,6-dimethylphenyl)acetic acid and 96.44% of (4'-fluoro-2,4-dimethylbiphenyl-3-yl)acetic acid [98% of theory].
To a mixture of 2a (0.22 g, 0.50 mmol) and 1b (0.15 g, 0.50 mmol) in ethanol (12 mL), Et3N (0.3 mL) was added in portions, and then the mixture was refluxed for 1 h. ;The reaction was cooled to room temperature, and ethyl ether (20 mL) was added slowly during 0.5 h.The solid was filtrated, washed with ethyl ether (3 * 10.0 mL) and water (3 * 10.0 mL) to afford the iodide salt..To a clear solution of the iodide salt (0.060 g, 0.125 mmol) under reflux sodium tetra(4-fluorophenyl)borate (0.083 g, 0.25 mmol) was added in portions, and then the mixture was heated under reflux for 1 h. ;The solid was filtrated and washed by ethanol to afford 4a as dark green powder.
To a mixture of 2a (0.22 g, 0.50 mmol) and 1b (0.15 g, 0.50 mmol) in ethanol (12 mL), Et3N (0.3 mL) was added in portions, and then the mixture was refluxed for 1 h. ;The reaction was cooled to room temperature, and ethyl ether (20 mL) was added slowly during 0.5 h.The solid was filtrated, washed with ethyl ether (3 * 10.0 mL) and water (3 * 10.0 mL) to afford the iodide salt..To a clear solution of the iodide salt (0.060 g, 0.125 mmol) under reflux sodium tetra(4-fluorophenyl)borate (0.083 g, 0.25 mmol) was added in portions, and then the mixture was heated under reflux for 1 h.The solid was filtrated and washed by ethanol to afford 4a as dark green powder.
To a mixture of 2a (0.22 g, 0.50 mmol) and 1b (0.15 g, 0.50 mmol) in ethanol (12 mL), Et3N (0.3 mL) was added in portions, and then the mixture was refluxed for 1 h. ;The reaction was cooled to room temperature, and ethyl ether (20 mL) was added slowly during 0.5 h.The solid was filtrated, washed with ethyl ether (3 * 10.0 mL) and water (3 * 10.0 mL) to afford the iodide salt..To a clear solution of the iodide salt (0.060 g, 0.125 mmol) under reflux sodium tetra(4-fluorophenyl)borate (0.083 g, 0.25 mmol) was added in portions, and then the mixture was heated under reflux for 1 h. ;The solid was filtrated and washed by ethanol to afford 4a as dark green powder.
To a mixture of 2a (0.22 g, 0.50 mmol) and 1b (0.15 g, 0.50 mmol) in ethanol (12 mL), Et3N (0.3 mL) was added in portions, and then the mixture was refluxed for 1 h. ;The reaction was cooled to room temperature, and ethyl ether (20 mL) was added slowly during 0.5 h.The solid was filtrated, washed with ethyl ether (3 * 10.0 mL) and water (3 * 10.0 mL) to afford the iodide salt..To a clear solution of the iodide salt (0.060 g, 0.125 mmol) under reflux sodium tetra(4-fluorophenyl)borate (0.083 g, 0.25 mmol) was added in portions, and then the mixture was heated under reflux for 1 h. The solid was filtrated and washed by ethanol to afford 4a as dark green powder.
2-[4-(<i>N</i>-acetyl-anilino)-buta-1,3-dienyl]-3-methyl-benzooxazolium; iodide[ No CAS ]
[ 25776-12-9 ]
[ 1403363-76-7 ]
Yield
Reaction Conditions
Operation in experiment
22%
To a mixture of 2a (0.22 g, 0.50 mmol) and 1b (0.15 g, 0.50 mmol) in ethanol (12 mL), Et3N (0.3 mL) was added in portions, and then the mixture was refluxed for 1 h. ;The reaction was cooled to room temperature, and ethyl ether (20 mL) was added slowly during 0.5 h.The solid was filtrated, washed with ethyl ether (3 * 10.0 mL) and water (3 * 10.0 mL) to afford the iodide salt..To a clear solution of the iodide salt (0.060 g, 0.125 mmol) under reflux sodium tetra(4-fluorophenyl)borate (0.083 g, 0.25 mmol) was added in portions, and then the mixture was heated under reflux for 1 h. ;The solid was filtrated and washed by ethanol to afford 4a as dark green powder.
To a mixture of 2a (0.22 g, 0.50 mmol) and 1b (0.15 g, 0.50 mmol) in ethanol (12 mL), Et3N (0.3 mL) was added in portions, and then the mixture was refluxed for 1 h. ;The reaction was cooled to room temperature, and ethyl ether (20 mL) was added slowly during 0.5 h.The solid was filtrated, washed with ethyl ether (3 * 10.0 mL) and water (3 * 10.0 mL) to afford the iodide salt..To a clear solution of the iodide salt (0.060 g, 0.125 mmol) under reflux sodium tetra(4-fluorophenyl)borate (0.083 g, 0.25 mmol) was added in portions, and then the mixture was heated under reflux for 1 h. ;The solid was filtrated and washed by ethanol to afford 4a
N-(3,5-bis(trifluoromethyl)phenyl)-N-tosylbenzamide[ No CAS ]
[ 25776-12-9 ]
[ 345-83-5 ]
Yield
Reaction Conditions
Operation in experiment
91%
With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; potassium carbonate; tricyclohexylphosphine; In 1,4-dioxane; at 110℃; for 10h;Inert atmosphere; Schlenk technique;
General procedure: Under a N2 atmosphere, to a 10 mL dry flask were added amide (0.5 mmol), sodium tetraarylborate (0.19 mmol), Pd(PCy3)2Cl2(5 mmol%), PCy3 (3 mmol%), K2CO3 (1 mmol), and dry dioxane (4 mL). The mixture was stirred at 110 C for a given time or monitored by TLC until the starting material was completely consumed. The reaction mixture was diluted with CH2Cl2 (15 mL), followed by washing with H2O (2 10 mL). The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel to afford product.
General procedure: A vial equipped with a screwcap was charged with a suspensionof 1avscl (1.0 mg, 8.5104 mmol), NaBPh4 (3a) (23.3 mg,0.068 mmol), and (2E)-3-biphenyl-4-ylprop-2-en-1-yl acetate (2a)(8.6 mg, 0.034 mmol) in H2O (1 mL). The mixture was agitated byshaking at 50 C for 10 min then allowed to cool to 25 C. The cooledmixture was extracted with t-BuOMe (41.0 mL), and the organiclayers were combined, dried over Na2SO4, and concentrated underreduced pressure. The residue was purified by chromatography(silica gel, hexane) to give 4-[(1E)-3-phenylprop-1-en-1-yl]biphenyl(4aa; 5.4 mg, 0.020 mmol, 59%) as a white solid.
With copper(II) acetate monohydrate; triethylamine; In acetonitrile; at 20℃; for 24h;
General procedure: A 10 mL vial was charged with the substrate amine 1 (0.2 mmol), NaBPh4 or NaBAr4 (0.1 mmol), and Cu(OAc)2·H2O (0.2 equiv) in MeCN (2 mL). To this mixture was added Et3N (2.0 equiv). The reaction mixture was then stirred at r.t. for 24 h. After completion of the reaction as monitored by TLC, the mixture was then concentrated through a rotary evaporator to yield the product, which was purified by direct flash column chromatography (Tables 2 and 3).
With magnesium; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere;
General procedure: Sodium tetraarylborates were prepared according to the literature, with some modifications. NaBF4 (1.0 g, 9.11 mmol) and Mg turnings(0.99 g, 41.00 mmol) were taken in an oven-dried sealed tube. The tube was filled with argon by the standard Schlenk technique. To this mixture, THF (20 mL) and 1,2-dibromoethane (40 μL, 0.46 mmol) were added, and the resulting mixture was stirred for 1 min. Finally,4-bromotoluene (4.7 mL, 38.3 mmol) was added in one shot at 0 C. A very exothermic reaction started immediately after the addition of aryl halide. After the apparent exotherm had ceased, the resulting suspension was stirred at r.t. for 12 h. The solution became gray and white precipitates were formed. The reaction mixture was then added to aq Na2CO3. The resulting mixture was stirred for 30 min and then extracted with MeCN (3 × 30 mL). The combined organic layerwas washed with brine (50 mL), dried over MgSO4, filtered and concentratedunder reduced pressure with a rotary evaporator. The crude residue was purified by precipitation using Et2O-hexane (1:2) to provide sodium tetra-4-tolylborate as a white powder; yield: 3.48 g (8.75mmol, 96%).
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 80℃; for 4h;Schlenk technique;
General procedure: A flame-dried Schlenk tube was charged with Pd2(dba)3 (5.71 mg,0.006 mmol) and SPhos (5.12 mg, 0.012 mmol) under argon. To this,anhydrous THF (31 mL) was added at r.t. The resulting dark brownish purple solution was brought to reflux at 80 C for 10 min to generate an active Pd-SPhos species, which was observed by a clear dark red coloration from purple during the course of heating. After the reaction mixture was cooled to r.t., 1a (0.50 g, 1.25 mmol) and sodium tetra-4-tolylborate (0.55 g, 1.37 mmol) were added. The mixture was again brought to 80 C for 1 h. After completion, the reaction mixture was filtered through a short bed of silica gel and the solvent was removed using a rotary evaporator. The crude mixture was purified by silica gel column chromatography (hexane) to provide 2b as a white solid; yield: 189 mg (1.12 mmol, 90%).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
