* 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.
With triethylamine; triphenylphosphine;palladium diacetate; at 120℃; for 18h;Inert atmosphere;
The aryl halide (2.1 mmol) and P(PPh)3 (0.82 mmol) were dissolved in triethylamine (3.15 mmol) in a glass pressure tube and nitrogen gas was bubbled through the solution via a gas dispersion tube for 10 minutes. Ethyl acrylate (2.3 mmol) and palladium acetate (0.41 mmol) were added to the reaction mixture and the tube was sealed and placed into an oil bath pre-heated to 120 0C for 18 h. The resulting solution was concentrated under vacuum and purified via an isco column. Retention time (min) = 2.416, method [1], MS(ESI) 260.1 (M+Eta).
Step 1: 2-bromo-1-iodo-3-trifluoromethyl-benzene An ice-cold solution of NaNO2 (0.15 g) in water (0.5 mL) is added to a mixture of <strong>[58458-10-9]2-bromo-3-trifluoromethyl-aniline</strong> (0.48 g), concentrated H2SO4 (2 mL), and water (1.8 mL) at ca. 5 C. The mixture is stirred in the cooling bath for 20 min and then poured into a solution of KI (0.56 g) and I2 (0.56 g) in water (0.5 mL). After ceasing of gas evolution, the mixture is heated to 40 C. and stirred at this temperature for 1 h. The mixture is cooled to room temperature and aqueous Na2SO3 solution is added. The resulting mixture is extracted with ethyl acetate and the combined extracts are dried (Na2SO4) and concentrated. The solvent is evaporated and the residue is chromatographed (cyclohexane/ethyl acetate 95:5?90:10) to give the title compound.
An ice-cold solution of NaNO2 (0.15 g) in water (0.5 mL) is added to a mixture of 2- bromo-3-trifluoromethyl-aniline (0.48 g), concentrated H2SO4 (2 mL), and water (1 .8 mL) at ca. 5 C. The mixture is stirred in the cooling bath for 20 min and then poured into a solution of Kl (0.56 g) and (0.56 g) in water (0.5 mL). After ceasing of gas evolution, the mixture is heated to 40 C and stirred at this temperature for 1 h. The mixture is cooled to room temperature and aqueous Na2SO3 solution is added. The resulting mixture is extracted with ethyl acetate and the combined extracts are dried (Na2SO4) and concentrated. The solvent is evaporated and the residue is chromatographed (cyclohexane/ethyl acetate 95:5?90 : 1 0 ) to g ive th e t itl e compound.
10.0 g
Step 1: 2-Bromo-3-trifluoromethyl-iodobenzene 2-Bromo-3-trifluoromethylaniline (8 g, 33.33 mmol) is suspended in water (90 mL) and cooled to 0 C. 96% H2SO4 (26.7 mL, 13.7 mmol) is added and the mixture stirred for 30 minutes. NaNO2 (2.41 g, 35 mmol) is dissolved in a small quantity of water and added dropwise at 0 C. The mixture is stirred for 30 minutes then potassium iodide (9.24 g, 55.66 mmol) and iodine (9.31 g, 36.66 mmol) in water are added dropwise with cooling. The mixture is stirred until gas evolution ceases then warmed to 40 C. and allowed to cool to room temperature. The mixture is shaken with excess aqueous Na2SO3 solution and extracted with ethyl acetate. The organic extracts are evaporated and the residue purified by flash chromatography (eluent:cyclohexane) to give the title compound (Yield 10.0 g) GC (GC METHOD 1): tR=8.40 min; Mass spectrum (EI+): m/z=350 [M]+.
10 g
Step 1: 2-Bromo-3-trifluoromethyl-iodobenzene2-Bromo-3-trifluoromethylaniline (8 g, 33.33 mmol) is suspended in water (90 ml) andcooled to 0 C. 96% H2S04 (26.7 ml, 13.7 mmol) is added and the mixture stirred for 30minutes. NaN02 (2.41 g, 35 mmol) is dissolved in a small quantity of water and addeddropwise at 0 C. The mixture is stirred for 30 minutes then potassium iodide (9.24 g,55.66 mmol) and iodine (9.31 g, 36.66 mmol) in water are added dropwise with cooling.The mixture is stirred until gas evolution ceases then warmed to 40 oc and allowed to coolto room temperature. The mixture is shaken with excess aqueous Na2S03 solutionandextracted with ethyl acetate. The organic extracts are evaporated and the residuepurified by flash chromatography (eluent: cyclohexane) to give the title compound (Yield10.0 g)GC (GC METHOD 1): tR = 8.40 min; Mass spectrum (EI+): m/z = 350 [Mf.
An ice-cold solution of NaNO2 (0.15 g) in water (0.5 mL) is added to a mixture of <strong>[58458-10-9]2-bromo-3-trifluoromethyl-aniline</strong> (0.48 g), concentrated H2SO4 (2 mL), and water (1.8 mL) at ca. 5 C. The mixture is stirred in the cooling bath for 20 min and then poured into a solution of KI (0.56 g) and I2 (0.56 g) in water (0.5 mL). After gas evolution ceases, the mixture is heated to 40 C. and stirred at this temperature for 1 h. The mixture is cooled to room temperature and aqueous Na2SO3 solution is added. The resulting mixture is extracted with ethyl acetate, and the combined extracts are dried (Na2SO4) and concentrated. The solvent is evaporated and the residue is chromatographed (cyclohexane/ethyl acetate 95:5?90:10) to give the title compound.
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In tetrahydrofuran; water;Reflux;
A mixture of 2-bromo-3-(tri r1uoromethyl)benzenamine (9.6 g; 40 mmol), 3,6-dihydro- 4-(4.4.5.5-tetramethyl- 1.3.2-dioxaborolan-2-yl )- 1.1-dimethylethylester- 1(2H)- pyridinecarboxilic acid (14.84 g; 48 mmol ). [l. l "-bis|bis( 1.1- dimethylethyl )phosphinoJferrocene]dichloro-palladium (652 mg; 1 mmol) and sodium carbonate (16.96 g; 160 mmol) in water (100 ml .) and THF (300 ml, ) was heated at reflux overnight. The solvent was removed under reduced pressure and the residue was solubilized with EtOAc and H20. The organic layer was separated, dried over MgSO.i, filtered and evaporated. The residue was purified by chromatography over silica gel (eluent: from 100% petrol ether to 50% petrol ether, 50% EtOAc). The pure fractions were collected and the solvent was evaporated to give 12 g (95%, white crystals) of intermediate 152
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
