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With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 95℃; for 12h;Inert atmosphere;
General procedure: A roundbottomed flask was charged with <strong>[13130-79-5]1-bromoisoquinolin-3-amine</strong> (4a, 0.300 g,1.34 mmol), 2-nitrophenylboronic acid (0.268 g, 1.61 mmol), Pd(PPh3)4(0.077 g, 0.067 mmol, 5 mol %), and Na2CO3 (0.284 g, 2.68 mmol) followed by adding toluene (8 mL), EtOH (4 mL) and H2O (0.5 mL). The mixture was flushed with argon for 5 min and, then, was heated under reflux for 12 h with magnetic stirring. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica using hexane/EtOAc (1:1) as the eluent yielding yellow crystals 3a (0.298 g, 84%, mp 154-155 C).
With copper(I) 2-hydroxy-3-methylbenzoate; potassium carbonate; In methanol; at 65℃; for 3h;
General procedure: A dry flask was charged with the nitrogen containing heterocycles (1 mmol), aryl boronic acids (2.2 mmol), potassium carbonate (2 mmol) andCuMeSal (0.015 mmol)then anhydrous methanol (10 ml) was added. The reaction mixture was stirred at 65 oC, open to air, for 3 h (5 h in case of indole and benzimidazole), cooled to room temperature, filtered, and the precipitate was washed with methanol (2 ml), the filtrate was concentrated under vacuum, then stirred with ice water (30 ml) and extracted with ethyl acetate (3 × 50 ml), dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by chromatography or recrystallization as indicated with each compound.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 85℃; for 4h;Inert atmosphere;
under nitrogen gas, 6-bromo-5-chloro-1H-indole (8.40g, 36.4mmol) in THF/H2O (80 ml/20 ml), 2-Nitrophenylboronic acid (6.08g, 36.4mmol), and K2CO3(15.1g, 0.109mol), Pd (PPh3)4(2.11g, 1.82mmol) , were added , in 85 C stirred 4 hours. Furthermore, after cooled to room temperature, was of concentrating the THF. After, ethyl which has organic layer which is then subjected to reverse phase, MgSO4in organic layer to the second interlayer, filters the concentrated within column chromatography for purifying the 4-chloro-6 - (2-nitrophenyl) - 1H-indole (8.44g, yield: 85%) is obtained.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 110℃; for 24h;Inert atmosphere;
A nitrogen atmosphere in a reaction flask in 2-Bromo-phenanthrene 30.0g (116.67 mmol), compound [23-1] 29.8g (151.67 mmol), tetrakis (triphenylphosphine) palladium, 4.04g (3.50 mmol), potassium carbonate 24.18g (175.00 mmol), 80mL of distilled water, 450mL of toluene was added and the mixture was stirred for 24 hours at 110 . After the reaction was solidified at room temperature was added to 1L of methanol. The resulting solid was filtered and stirred under reflux in acetone 300mL. After cooling to room temperature, filtered and dried in the yellow-green solid intermediate compound [23-2] was prepared in 26g (67wtpercent).
With potassium fluoride; In dimethyl sulfoxide; at 130℃; for 2h;Inert atmosphere;
General procedure: The mixture of phenylboronic acid (1 mmol), aromatic amine (1.2 mmol) and 0.12 g (2 mmol) of KF in DMSO (4 mL) were added to Cu-IS-AMBA-MNPs (0.06 g, 0.025 mmol) at 130 °C under nitrogen atmosphere for 2 h with vigorous stirring. Then, after completion of the reaction, the catalyst was separated by an external magnet and washed with dry CH2Cl2 three times and checked for its reusability. The solvent of the reaction mixture was evaporated by a rotary evaporator and then ethyl acetate and water were added to the residue. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography using ethyl acetate/n-hexane.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Reflux;
<strong>[1097884-37-1]4-bromo-9-phenylcarbazole</strong> 50g (135.4 mmol), 2-nitrophenyl boronic acid 26.9g (148.9 mmol), Pd(PPh3)47.8g (6.8 mmol), potassium carbonate 37.4g (270.8 mmmol) ) Was suspended in 680 ml of toluene, 135 ml of ethyl alcohol, and 135 ml of distilled water, and then stirred under reflux for 12 hours.After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and purified by a silica gel column to obtain Compound 2-1, 24.7g (yield: 50%).
50%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Reflux;
<strong>[1097884-37-1]4-bromo-9-phenylcarbazole</strong> 50g (135.4 mmol), 2-nitrophenyl boronic acid 26.9g (148.9 mmol), Pd(PPh3)4 7.8g (6.8mmol), potassium carbonate 37.4g (270.8mmol) was suspended in a solution consisting of 680 ml of toluene, 135 ml of ethyl alcohol, and 135 ml of distilled water, followed by stirring under reflux for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer (dichloromethane layer) was distilled under reduced pressure and then subjected to silica gel column to obtain Compound 2-1, 24.7 g (yield: 50%) was obtained.
With trans-bis(triphenylphosphine)palladium dichloride; cesium fluoride; In 1,4-dioxane; water; at 50℃;
To a solution of <strong>[689291-89-2]5-bromo-2-iodobenzaldehyde</strong> (620 mg, 1.99 mmol) in 1,4-dioxane/water (10/4 mL ) was added CsF (909 mg, 5.98 mmol), PdCl2(PPh3)2 (30 mg, 0.04 mmol) and 2-nitrophenylboronic acid (333 mg, 1.99 mmol). This mixture was stirred at 50 C overnight. The reaction mixture was diluted with water and extracted with EtOAc (3x20 mL). The organic layer was washed with brine and concentrated to dryness to give crude residue, which was purified by column chromatography on silica gel (petroleum ether / EtOAc = 10/1 to 8/1) to give 170-1 (410 mg, about 67% yield) as an oil. MS Calcd.: 305.0; MS Found: 323.2 [M + H]+.
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