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With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 12h;Inert atmosphere; Reflux;
2.4 g of 3,9-dibromo-indenofluorenedione was mixed with 3.4 g of 3,5-bis(trifluoromethyl)phenylboronic acid, 0.23 g of tetraxis(triphenylenephosphine)palladium (0), 20 ml of 2M sodium carbonate and 130 ml of toluene under argon stream. The mixture was stirred with reflux for 12 hours. After cooling, the reaction liquid was filtered, washed with water and methanol, whereby 3.5 g of a reddish purple solid as an intermediate A was obtained.As a result of mass spectroscopy of the resulting solid, a peak was observed at M/Z=706.
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; toluene; at 20 - 125℃;sealed microwave vial;
Preparation of i-1 bStep A: Preparation of methyl 2-amino-3',5'-bis(trifluoromethyl)biphenyl-4-carboxylate (i-Ia)[l 5r-Bis(diphenylphosphino)ferrocene]dichloropaIladium(II) (265 mg, 0,360 mmol) was added to a solution of <strong>[412947-54-7]methyl 3-amino-4-iodobenzoate</strong> (2.00 g, 7.22 mmol)f 3,5- bistrifluorophenylboronic acid (2.05 g, 7.94 mmol) and sodium carbonate (5.40 mL of a 2.0 M aqueous solution, 10.83 mmol) in EtOH:toluene (12.0 mL of an 80:20 mixture, respectively) at rt. The resulting solution was heated to 125 C in a sealed microwave vial for 20 min. After cooling to rt, the reaction mixture was filtered through a short column of Celite, eluting with EtOAc. The filtrate was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (isocratic elution; 10% EtOAc/hexanes as eluent) to furnish the title compound i-la. m/z (ES) 364 (MH)+.
With bis(eta3-allyl-mu-chloropalladium(II)); 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-4,5-dihydroimidazolinium chloride; In tetrahydrofuran; water; at 100℃; for 2h;Inert atmosphere; Sealed tube;
General procedure: [PdCl(eta3-allyl)]2 (0.00125-0.005 mmol), imidazolinium salt 1a (0.0025-0.01 mmol), arylboronic acid (0.50 mmol) and an inorganic base (2.0 mmol) were charged in a 10 mL test tube sealed with a rubber septum. The test tube was evacuated and backfilled with argon. This sequence was repeated five times. Then solvent (0.5 mL) and 37 wt % formaldehyde in H2O (102 mg, formaldehyde 1.25 mmol) were added via the rubber septum with syringe. In anargon flow, the rubber septum was replaced with a Teflon liners crew cap. The test tube was placed in an oil bath preheated at 100 C. The reaction mixture was stirred for 2 h and was cooled to room temperature. Then, operation of (i) or (ii) was performed. (i)The obtained crude was purified by passing it through a silica gel column with a hexane/ethyl acetate eluent (Table 4 entry 2 and Table 5 entries 8-16). (ii) Diphenylmethane (84.1 mg, 0.50 mmol) as an internal standard was added and then an aliquot of the organic layer of the reaction mixture was subjected to the quantitative analysis by 1H NMR (Table 4).
2-(3,5-bis(trifluoromethyl)phenyl)-1-(pyrimidin-2-yl)-1H-indole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
98%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;
General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.
With 4-nitrophenylhydrazone; cesium fluoride; at 80℃; for 12h;
25 mL reaction flaskNitrophenylhydrazine (0.25 mmol)3,5-bis-trifluoromethyl-phenyl boronic acid (0.5mmol),Cesium fluoride (2.0 mmol)And polyethylene glycol-400 (2.0 g).The mixture was reacted at 80 C until the reaction was complete.The reaction mixture was cooled to room temperature,The product was isolated by column chromatography after evaporation of the solvent under reduced pressure. The yield was 87%.
With palladium diacetate; potassium carbonate; In ethanol; water; toluene; at 80℃; for 12h;
5,5'-Dibromo-2,2'-bisthiophene (0.325 g, 1.0 mmol), (3,5-bis(trifluoromethyl)phenyl)boronic acid (0.774 g, 3.0 mmol),Palladium acetate (0.0058 g, 0.03 mmol) and potassium carbonate (0.415 g, 3.0 mmol) were mixed in a 100 mL reaction apparatus, and then a mixed liquid of 18 mL of toluene, 9 mL of ethanol, and 3 mL of water was added, and the mixture was reacted at 80 C for 12 hours.After completion of the reaction, the mixture was separated and evaporated with dichloromethane.The solvent was removed by a rotary evaporator to obtain a solid powder, which was then separated from the column using pure petroleum ether as a solvent and recrystallized from petroleum ether.An organic compound of 5-(3,5-bis(trifluoromethyl)phenyl)-2,2'-bisthiophene was obtained in a yield of 60%.
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